Synthesis of 3-Alkyl Spiro[4,5]trienones by

Copper-Catalyzed Oxidative ipso-

Annulation of Activated Alkynes with

Unactivated Alkanes

Xuan-Hui Ouyang,† Ren-Jie Song,*† Bang Liu,† and Jin-Heng Li*†

†State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry

and Chemical Engineering, Hunan University, Changsha 410082, China

srj0731@hnu.edu.cn and jhli@hnu.edu.cn

Supporting Information

List of Contents

(A) Typical experimental procedure

(B) Analytical data

(C) Reference

(D) Spectra

Electronic Supplementary Material (ESI) for ChemComm.This journal is © The Royal Society of Chemistry 2015

(A) Typical experimental procedure

(a) Synthesis of Substrates 1:

All of compounds 1 were synthesized according to the known literatures, and the

NMR spectra were consisted with the reported data.[S1]

(b) Typical Experimental Procedure Copper-Mediated Oxidative for the

Difunctionalization of N-Arylpropiolamides (1) with Unactivated Alkanes C(sp3)-

H Bonds (2):

To a Schlenk tube were added N-arylpropiolamide 1 (0.3 mmol), Cu(OAc)2 (10

mol%), TBHP (anhydrous, 3 equiv) and alkane (1 mL). Then the tube was charged

with argon, and was stirred at 110 oC for 36 h. After the reaction was finished, the

reaction mixture was cooled to room, then concentrated in vacuum, and the resulting

residue was purified by silica gel column chromatography (hexane/ethyl acetate) to

afford the desired product and the N-arylpropiolamide was recovered.

(c) The 18O-labeled experiment:

O

N O

50.0 75.0 100.0 125.0 150.0 175.0 200.0 225.0 250.0 275.0 300.0 325.0 350.0 375.0 400.0 425.0 450.00

25

50

75

100

%

333

278129 165115 211 290178 223 25091 30455 77

405355 377 417 437

[MS Spectrum]

# of Peaks 338

Raw Spectrum 18.595 (scan :

3020) Base Peak m/z

333.20 (Inten : 84,557)

Background 18.520 (scan :

3005)

m/z Absolute Intensity

Relative Intensity

50.00 163 0.19

51.00 1376 1.63

52.00 598 0.71

53.00 1389 1.64

54.10 637 0.75

55.10 4224 5.00

56.10 957 1.13

57.10 310 0.37

58.05 4017 4.75

59.10 87 0.10

60.10 40 0.05

62.10 244 0.29

63.05 1129 1.34

64.00 401 0.47

65.05 1558 1.84

66.05 2035 2.41

67.05 2956 3.50

68.05 987 1.17

69.00 347 0.41

70.00 315 0.37

71.00 39 0.05

72.00 39 0.05

74.10 209 0.25

75.05 1051 1.24

76.05 1309 1.55

77.05 3809 4.50

78.00 1536 1.82

79.05 2008 2.37

80.10 606 0.72

81.05 1783 2.11

82.05 708 0.84

83.05 896 1.06

84.00 519 0.61

85.00 24 0.03

86.00 137 0.16

87.00 261 0.31

88.00 750 0.89

89.05 1690 2.00

90.10 519 0.61

91.05 5122 6.06

92.10 1135 1.34

93.10 1771 2.09

94.15 801 0.95

95.05 1220 1.44

96.10 962 1.14

97.10 276 0.33

98.10 704 0.83

99.10 129 0.15

100.10 295 0.35

101.05 1467 1.73

102.10 3069 3.63

103.05 1454 1.72

104.00 678 0.80

105.00 1820 2.15

106.10 798 0.94

107.10 1614 1.91

108.15 695 0.82

109.15 602 0.71

110.10 1475 1.74

111.10 296 0.35

112.10 1475 1.74

113.10 610 0.72

114.10 857 1.01

115.05 8402 9.94

116.05 1817 2.15

117.05 2035 2.41

118.05 4011 4.74

119.05 910 1.08

120.05 1521 1.80

121.10 3210 3.80

122.15 1453 1.72

123.20 2494 2.95

124.15 1362 1.61

125.20 340 0.40

126.10 936 1.11

127.10 2979 3.52

128.10 5980 7.07

129.05 8998 10.64

130.05 2567 3.04

131.05 1966 2.33

132.05 837 0.99

133.05 214 0.25

134.05 694 0.82

135.20 397 0.47

136.20 603 0.71

137.10 466 0.55

138.15 1267 1.50

139.05 2074 2.45

140.10 954 1.13

141.10 7301 8.63

142.10 2462 2.91

143.10 1352 1.60

144.10 1380 1.63

145.05 1230 1.45

146.10 1111 1.31

147.05 299 0.35

148.10 221 0.26

149.10 405 0.48

150.10 1034 1.22

151.10 1883 2.23

152.10 5515 6.52

153.10 4372 5.17

154.10 1646 1.95

155.10 3534 4.18

156.10 1556 1.84

157.15 1309 1.55

158.15 1026 1.21

159.20 431 0.51

160.20 789 0.93

161.20 57 0.07

162.00 353 0.42

163.05 1332 1.58

164.10 1474 1.74

165.05 8483 10.03

166.10 2858 3.38

167.10 3255 3.85

168.05 1635 1.93

169.10 1347 1.59

170.10 784 0.93

171.10 440 0.52

172.10 820 0.97

173.10 369 0.44

174.10 759 0.90

175.10 439 0.52

176.10 1981 2.34

177.10 1779 2.10

178.15 6907 8.17

179.10 5078 6.01

180.10 2675 3.16

181.10 4243 5.02

182.10 2220 2.63

183.15 3530 4.17

184.10 1946 2.30

185.10 661 0.78

186.10 456 0.54

187.10 512 0.61

188.10 1000 1.18

189.10 3945 4.67

190.10 2968 3.51

191.10 4621 5.46

192.15 2532 2.99

193.10 2549 3.01

194.10 4308 5.09

195.10 1888 2.23

196.10 1214 1.44

197.10 1102 1.30

198.05 880 1.04

199.10 451 0.53

200.10 763 0.90

201.10 800 0.95

202.10 3058 3.62

203.10 3355 3.97

204.15 2455 2.90

205.10 3317 3.92

206.10 2464 2.91

207.05 5822 6.89

208.05 5156 6.10

209.05 2685 3.18

210.15 2586 3.06

211.10 8261 9.77

212.10 2521 2.98

213.10 663 0.78

214.10 499 0.59

215.10 1610 1.90

216.15 949 1.12

217.10 1437 1.70

218.10 2813 3.33

219.10 2548 3.01

220.05 2774 3.28

221.10 2563 3.03

222.10 3976 4.70

223.10 5691 6.73

224.15 2466 2.92

225.10 634 0.75

226.10 247 0.29

227.10 499 0.59

228.10 760 0.90

229.10 642 0.76

230.10 514 0.61

231.05 1419 1.68

232.15 1775 2.10

233.10 4446 5.26

234.10 3664 4.33

235.10 2649 3.13

236.10 3426 4.05

237.10 1306 1.54

238.05 967 1.14

239.10 290 0.34

240.15 1006 1.19

241.20 313 0.37

242.20 395 0.47

243.20 279 0.33

244.20 591 0.70

245.10 1031 1.22

246.05 1643 1.94

247.10 2755 3.26

248.10 3435 4.06

249.05 1577 1.87

250.05 5285 6.25

251.10 4152 4.91

252.15 2736 3.24

253.05 569 0.67

254.10 122 0.14

255.10 131 0.15

256.10 2419 2.86

257.10 642 0.76

258.10 366 0.43

259.10 726 0.86

260.10 1544 1.83

261.10 1515 1.79

262.10 2992 3.54

263.10 1547 1.83

264.10 7313 8.65

265.10 5707 6.75

266.10 1517 1.79

268.00 25 0.03

269.00 99 0.12

270.00 6 0.01

271.00 114 0.13

272.00 210 0.25

273.10 1176 1.39

274.15 1333 1.58

275.10 2120 2.51

276.10 6933 8.20

277.15 2644 3.13

278.10 13827 16.35

279.15 3010 3.56

280.10 490 0.58

284.00 6 0.01

285.00 122 0.14

286.00 337 0.40

287.00 228 0.27

288.00 727 0.86

289.10 573 0.68

290.15 6937 8.20

291.15 2215 2.62

292.15 2960 3.50

293.20 603 0.71

294.20 61 0.07

298.20 49 0.06

299.20 10 0.01

300.20 63 0.07

301.20 510 0.60

302.20 499 0.59

303.20 713 0.84

304.15 4702 5.56

305.20 2045 2.42

306.20 377 0.45

307.20 67 0.08

308.20 39 0.05

310.20 32 0.04

312.20 7 0.01

313.20 38 0.04

314.20 219 0.26

315.20 20 0.02

316.20 1367 1.62

317.20 433 0.51

318.15 1859 2.20

319.20 436 0.52

320.20 100 0.12

321.20 29 0.03

324.20 15 0.02

328.20 1 0.00

330.20 61 0.07

331.15 569 0.67

332.15 75790 89.63

333.20 84557 100.00

334.20 18293 21.63

335.15 2566 3.03

336.10 128 0.15

337.10 47 0.06

338.10 6 0.01

341.10 13 0.02

342.10 67 0.08

343.10 77 0.09

344.10 30 0.04

345.10 13 0.02

346.10 33 0.04

347.10 51 0.06

348.10 68 0.08

350.10 8 0.01

351.10 7 0.01

354.10 7 0.01

355.10 117 0.14

359.10 53 0.06

360.10 27 0.03

361.10 20 0.02

362.10 36 0.04

364.10 4 0.00

365.10 43 0.05

366.10 4 0.00

368.10 15 0.02

369.10 6 0.01

372.10 8 0.01

374.10 22 0.03

375.10 1 0.00

377.10 46 0.05

378.10 42 0.05

379.10 40 0.05

382.10 9 0.01

383.10 14 0.02

386.10 12 0.01

388.10 8 0.01

391.10 56 0.07

392.10 8 0.01

393.10 40 0.05

399.10 30 0.04

402.10 51 0.06

403.10 1 0.00

405.10 177 0.21

406.10 3 0.00

407.10 13 0.02

408.10 37 0.04

409.10 21 0.02

412.10 20 0.02

413.10 12 0.01

415.10 27 0.03

416.10 5 0.01

417.10 40 0.05

418.10 30 0.04

419.10 24 0.03

422.10 14 0.02

424.10 17 0.02

425.10 10 0.01

426.10 20 0.02

427.10 7 0.01

428.10 4 0.00

431.10 33 0.04

433.10 31 0.04

434.10 34 0.04

436.10 35 0.04

437.10 38 0.04

440.10 2 0.00

442.10 7 0.01

443.10 9 0.01

444.10 6 0.01

446.10 22 0.03

448.10 7 0.01

18ON O

50.0 75.0 100.0 125.0 150.0 175.0 200.0 225.0 250.0 275.0 300.0 325.0 350.0 375.0 400.0 425.0 450.00

25

50

75

100

%

332

278165129 211115 290178 223 30491 25158 77 356 401387 439432

[MS Spectrum]

# of Peaks 274

Raw Spectrum 19.335 (scan :

3168) Base Peak m/z

333.10 (Inten : 58,078)

Background 19.290 (scan :

3159)

m/z Absolute Intensity

Relative Intensity

51.00 62 0.11

52.00 818 1.41

53.00 444 0.76

54.95 2807 4.83

56.00 858 1.48

57.90 2568 4.42

58.90 368 0.63

61.90 295 0.51

62.90 638 1.10

64.85 1021 1.76

66.05 1747 3.01

67.15 1788 3.08

70.20 826 1.42

73.05 277 0.48

75.00 381 0.66

76.00 811 1.40

77.10 2493 4.29

77.90 648 1.12

78.90 1174 2.02

79.90 302 0.52

80.90 370 0.64

81.90 475 0.82

82.90 376 0.65

85.90 107 0.18

86.90 306 0.53

87.80 18 0.03

88.80 1182 2.04

90.10 490 0.84

91.10 3863 6.65

91.90 695 1.20

92.95 1181 2.03

94.25 1587 2.73

94.80 497 0.86

95.85 76 0.13

96.80 376 0.65

98.80 90 0.15

99.80 220 0.38

100.70 337 0.58

101.75 1461 2.52

102.75 905 1.56

104.05 968 1.67

105.20 1510 2.60

106.95 1013 1.74

108.00 625 1.08

108.80 338 0.58

109.75 882 1.52

110.80 438 0.75

111.80 290 0.50

112.80 256 0.44

114.00 683 1.18

115.05 5724 9.86

116.10 937 1.61

117.05 1124 1.94

118.05 3203 5.51

119.65 902 1.55

121.00 2382 4.10

122.55 1568 2.70

123.60 1081 1.86

125.60 502 0.86

126.80 1772 3.05

128.05 4260 7.33

129.05 6451 11.11

130.05 1050 1.81

130.95 1525 2.63

132.50 1718 2.96

135.05 1738 2.99

136.00 359 0.62

138.00 1403 2.42

139.10 1890 3.25

140.95 4391 7.56

142.00 2550 4.39

143.45 1696 2.92

144.90 1642 2.83

146.25 1436 2.47

149.20 1225 2.11

150.65 567 0.98

152.00 4472 7.70

153.10 2962 5.10

153.80 348 0.60

154.85 2095 3.61

156.10 2156 3.71

157.10 521 0.90

159.10 975 1.68

160.10 802 1.38

163.05 1966 3.39

163.90 184 0.32

164.90 5218 8.98

166.00 3203 5.51

167.15 3073 5.29

167.90 277 0.48

168.85 1172 2.02

169.90 814 1.40

172.90 969 1.67

173.90 119 0.20

175.90 1478 2.54

177.10 2517 4.33

178.05 4332 7.46

179.05 2088 3.60

180.00 3284 5.65

181.15 3648 6.28

182.05 456 0.79

182.95 2457 4.23

184.15 1862 3.21

187.10 1079 1.86

188.10 826 1.42

189.05 1314 2.26

190.05 1460 2.51

191.05 3130 5.39

191.90 1066 1.84

192.85 910 1.57

194.10 3643 6.27

195.30 1863 3.21

196.00 3 0.01

196.95 846 1.46

198.00 858 1.48

200.00 30 0.05

200.70 289 0.50

201.75 1423 2.45

202.70 1769 3.05

204.00 2119 3.65

205.15 3092 5.32

206.05 1315 2.26

206.95 1968 3.39

208.00 3433 5.91

209.05 1992 3.43

209.95 1145 1.97

211.00 6025 10.37

212.20 2335 4.02

215.10 1914 3.30

215.70 127 0.22

216.70 1027 1.77

218.00 1683 2.90

218.95 1856 3.20

219.90 1909 3.29

220.90 1357 2.34

222.05 3482 6.00

223.00 3921 6.75

223.95 1493 2.57

225.00 790 1.36

226.00 156 0.27

228.00 424 0.73

229.00 937 1.61

230.75 1070 1.84

232.05 1833 3.16

233.05 2795 4.81

233.95 2035 3.50

234.95 1895 3.26

236.10 3409 5.87

237.10 526 0.91

239.10 766 1.32

240.10 703 1.21

242.10 90 0.15

243.10 722 1.24

246.10 1748 3.01

246.95 1187 2.04

247.85 1837 3.16

248.95 1394 2.40

250.15 4400 7.58

251.05 2058 3.54

251.95 1689 2.91

253.00 936 1.61

254.00 336 0.58

256.00 1017 1.75

257.00 604 1.04

259.00 391 0.67

260.00 1221 2.10

260.80 287 0.49

261.80 2101 3.62

263.05 1490 2.57

264.10 5151 8.87

265.05 2335 4.02

265.85 1970 3.39

267.10 1633 2.81

270.10 980 1.69

271.10 284 0.49

273.10 1192 2.05

274.20 1769 3.05

274.90 589 1.01

275.95 3913 6.74

277.05 2737 4.71

278.00 9498 16.35

278.95 1287 2.22

280.05 1292 2.22

283.80 251 0.43

286.80 397 0.68

287.80 30 0.05

289.95 3568 6.14

291.10 2186 3.76

292.20 2623 4.52

294.20 28 0.05

295.20 671 1.16

298.20 830 1.43

299.20 169 0.29

301.20 326 0.56

302.20 953 1.64

304.00 2880 4.96

305.10 2324 4.00

306.10 342 0.59

308.10 413 0.71

309.10 220 0.38

312.10 714 1.23

315.10 580 1.00

316.10 1108 1.91

317.90 1344 2.31

318.90 383 0.66

321.90 566 0.97

324.90 228 0.39

325.90 49 0.08

327.90 222 0.38

328.90 849 1.46

331.15 1127 1.94

332.10 55127 94.92

333.10 58078 100.00

334.10 18054 31.09

335.00 8480 14.60

336.10 2438 4.20

339.10 578 1.00

340.10 540 0.93

343.10 964 1.66

346.10 1063 1.83

347.10 446 0.77

349.10 88 0.15

350.10 726 1.25

353.10 626 1.08

354.10 340 0.59

356.10 333 0.57

357.10 894 1.54

360.10 686 1.18

361.10 142 0.24

363.10 258 0.44

364.10 626 1.08

367.10 724 1.25

368.10 6 0.01

370.10 345 0.59

371.10 577 0.99

374.10 782 1.35

377.10 538 0.93

378.10 516 0.89

381.10 719 1.24

384.10 490 0.84

385.10 462 0.80

388.10 788 1.36

391.10 610 1.05

392.10 346 0.60

394.10 13 0.02

395.10 676 1.16

398.10 630 1.08

399.10 292 0.50

401.10 181 0.31

402.10 714 1.23

405.10 1356 2.33

406.10 330 0.57

408.10 318 0.55

409.10 626 1.08

412.10 706 1.22

413.10 84 0.14

415.10 398 0.69

416.10 642 1.11

419.10 812 1.40

422.10 398 0.69

423.10 537 0.92

426.10 718 1.24

429.10 721 1.24

430.10 559 0.96

433.10 735 1.27

436.10 540 0.93

437.10 338 0.58

439.10 41 0.07

440.10 689 1.19

443.10 633 1.09

444.10 273 0.47

446.10 138 0.24

447.10 671 1.16

450.10 644 1.11

(B) Analytical data

3-Cyclohexyl-1-methyl-4-phenyl-1-azaspiro[4.5]deca-

3,6,9-triene-2,8-dione (3aa):

Yellow solid; mp: 126.1-127.9 oC (uncorrected); 1H NMR

(400 MHz, CDCl3) : 7.33-7.28 (m, 3H), 7.05 (d, J = 6.0 Hz, 2H), 6.48 (d, J = 9.6 Hz,

2H), 6.37 (d, J = 10.0 Hz, 2H), 2.87 (s, 3H), 2.47-2.41 (m, 1H), 1.75-1.65 (m, 4H),

1.63-1.53 (m, 3H), 1.23-1.12 (m, 3H); 13C NMR (400 MHz, CDCl3) : 184.2, 170.5,

148.7, 145.9, 142.1, 132.8, 131.6, 128.8, 128.5, 128.1, 67.4, 36.9, 30.4, 26.2, 25.9,

25.5; IR (KBr, cm-1): 1702, 1686; LRMS (EI, 70 eV) m/z (%): 333 (M+, 100), 332

(90), 207 (26); HRMS m/z (ESI) calcd for C22H24NO2 ([M+H]+) 334.1802, found

334.1806.

N

O

O

12

3

4 5 1-Methyl-3-(methylcyclohexyl)-4-phenyl-1-azaspiro[4.5]deca-

3,6,9-triene-2,8-dione and 3-(Cyclohexylmethyl)-1-methyl-4-phenyl-1-

azaspiro[4.5]deca-3,6,9-triene-2,8-dione (3ab):

2/3/4/5 = 1.4:4.8:2.7:1.1

Yellow oil; 1H NMR (400 MHz, CDCl3) : 7.30 (m, 3.0H), 7.12-6.93 (m, 2.0H),

6.59-6.24 (m, 4.0H), 2.88 (s, 3.0H), 2.76 (m, 0.5H), 2.52-2.26 (m, 0.9H), 2.20-1.83

(m, 1.9H), 1.80-1.17 (m, 10.9H), 0.96-0.77 (m, 3.3H); 13C NMR (125 MHz, CDCl3) :

184.1, 170.4, 146.1, 146.0, 145.91, 132.8, 132.8, 128.9, 128.8, 128.4, 128., 128.1,

128.1, 128.1, 127.3, 67.5, 67.3, 38.7, 38.3, 36.7, 36.6, 36.4, 35.8, 35.7, 34.9, 34.7,

ON O

34.1, 32.4, 31.6, 31.3, 30.7, 30.4, 30.2, 29.5, 27.2, 26.2, 25.9, 25.8, 24.3, 22.5, 20.3,

17.3, 17.0; HRMS m/z (ESI) calcd for C23H26NO3 ([M+H]+) 347.1885, found

347.1894.

3-Cyclopentyl-1-methyl-4-phenyl-1-azaspiro[4.5]deca-

3,6,9-triene-2,8-dione (3ac):

Yellow solid; mp: 110.3-111.7 oC(uncorrect); 1H NMR

(400 MHz, CDCl3) : 7.34 -7.29 (m, 3H),7.11-7.10 (m, 2H), 6.51 (d, J = 9.2 Hz, 2H),

6.40 (d, J = 9.6 Hz, 2H), 2.88 (s, 3H), 2.82-2.73 (m, 1H), 1.93-1.89 (m, 2H), 1.80-

1.63 (m, 4H), 1.53-1.52 (m, 2H); 13C NMR (100 MHz, CDCl3) : 184.2, 170.1, 148.6,

146.0, 140.7, 132.8, 131.6, 128.9, 128.4, 128.3, 67.1, 37.2, 31.1, 26.2, 25.7; IR (KBr,

cm-1): 1681, 1662; LRMS (EI, 70 eV) m/z (%): 319 (M+, 78), 318 (100), 278 (18);

HRMS m/z (ESI) calcd for C21H22NO2 ([M+H]+) 320.1645, found 320.1653.

3-Cycloheptyl-1-methyl-4-phenyl-1-azaspiro[4.5]deca-

3,6,9-triene-2,8-dione (3ad):

Yellow solid; mp: 116.1-117.7 oC(uncorrect); 1H NMR

(400 MHz, CDCl3) : 7.34-7.29 (m, 3H), 7.08-7.06 (m, 2H), 6.48 (d, J = 9.2 Hz, 2H),

6.38 (d, J = 9.2 Hz, 2H), 2.88 (s, 3H), 2.61-2.56 (m, 1H), 1.89-1.81 (m, 2H), 1.73-

1.64 (m, 4H), 1.52-1.46 (m, 4H), 1.41-1.36 (m, 2H); 13C NMR (100 MHz, CDCl3) :

184.1, 170.4, 147.0, 145.9, 143.8, 132.7, 131.6, 128.8, 128.4, 128.1, 67.3, 38.2, 32.7,

27.6, 27.4, 25.8; IR (KBr, cm-1): 1680, 1661; LRMS (EI, 70 eV) m/z (%): 347 (M+,

100), 278 (18), 65 (36); HRMS m/z (ESI) calcd for C23H26NO2 ([M+H]+) 348.1958,

found 348.1974.

ON O

ON O

3-Cyclooctyl-1-methyl-4-phenyl-1-azaspiro[4.5]deca-

3,6,9-triene-2,8-dione (3ae):

Yellow solid; mp: 115.1-117.5 oC(uncorrect); 1H NMR

(400 MHz, CDCl3) : 7.34-7.32 (m, 3H), 6.49 (d, J = 9.2 Hz, 2H), 6.38 (d, J = 9.2 Hz,

2H), 2.87 (s, 3H), 2.69 (t, J = 9.2 Hz, 1H), 1.96-1.88 (m, 2H), 1.69-1.67 (m, 2H),

1.60-1.40 (m, 10H); 13C NMR (100 MHz, CDCl3) : 184.1, 170.6, 146.8, 146.9, 144.4,

132.7, 131.5, 128.7, 128.4, 128.1, 67.2, 35.7, 31.5, 26.1 (2C), 25.9, 25.8; IR (KBr,

cm-1): 1683, 1666, 1630; LRMS (EI, 70 eV) m/z (%): 361 (M+, 100), 265 (25), 278

(23); HRMS m/z (ESI) calcd for C24H28NO2 ([M+H]+) 362.2115, found 362.2128.

3-Hexanyl-1-methyl-4-phenyl-1-azaspiro[4.5]deca-3,6,9-

triene-2,8-dione (3af):

2/3 = 6.1/3.9

Yellow oil; 1H NMR (400 MHz, CDCl3) :7.37-7.29 (m, 3.0H), 7.10-7.00 (m,

2.0H), 6.62-6.36 (m, 4.0H), 2.89 (s, 3.0H), 2.71 (s, 0.8H), 2.61-2.50 (m, 0.8H), 2.19 (s,

1.2H), 1.86-1.71 (m, 2.0H), 1.56-1.44 (m, 2.0H), 1.28-1.13 (m, 6.3H), 0.86-0.81(m,

4.7H); 13C NMR (125 MHz, CDCl3) : 184.2, 170.2, 150.7, 149.1, 146.0, 145.9, 142.0,

140.3, 133.0, 132.9, 132.8, 131.4, 128.9, 128.8, 128.7, 128.5, 128.2, 128.1, 67.7, 67.5,

39.3, 36.9, 34.9, 33.8, 31.9, 30.3, 29.9, 25.9, 25.9, 25.8, 22.5, 21.3, 19.1, 14.1, 14.0,

12.7; HRMS m/z (ESI) calcd for C22H26NO2 ([M+H]+) 336.1958., found 336.1945.

1-Methyl-4-phenyl-3-(1-phenylethyl)-1-

azaspiro[4.5]deca-3,6,9-triene-2,8-dione (3ag):

ON O

ON O

N

O

O

12

3

Yellow oil; 1H NMR (400 MHz, CDCl3) : 7.32-7.23 (m, 7H), 7.19-7.17 (m, 1H),

7.01 (d, J = 6.4 Hz, 2H), 6.48 (t, J = 9.2 Hz, 2H), 6.37 (t, J = 10.0 Hz, 2H), 4.13-3.81

(m, 1H), 2.86 (s, 3H), 1.59 (d, J = 7.2 Hz, 3H); 13C NMR (125 MHz, CDCl3) : 184.1,

169.9, 149.6, 145.6, 145.5, 142.9, 141.1, 133.0, 132.9, 131.0, 129.0, 128.5, 128.3,

128.2, 127.5, 126.4, 67.5, 36.8, 26.0, 18.3; IR (KBr, cm-1): 1664, 1683; LRMS (EI, 70

eV) m/z (%): 355 (M+, 100), 207 (56), 283 (24), 355 (100); HRMS m/z (ESI) calcd for

C24H22NO2 ([M+H]+) 356.1645, found 356.1657.

3-Benzyl-1-methyl-4-phenyl-1-azaspiro[4.5]deca-3,6,9-

triene-2,8-dione (3ai):

Yellow oil; 1H NMR (400 MHz, CDCl3) : 7.38-7.30

(m, 3H), 7.26-7.17 (m, 3H), 7.15-7.09(m, 4H), 6.50 (d, J = 8.0 Hz, 2H), 6.42 (d, J =

8.0 Hz, 2H), 3.68 (s, 2H), 2.90 (s, 3H); 13C NMR (100 MHz, CDCl3) : 184.1, 170.6,

150.6, 145.6, 138.2, 137.2, 133.0, 131.0, 129.3, 128.6, 128.5, 128.3, 126.4, 67.6. 30.8,

26.1; IR (KBr, cm-1): 1660, 1682; LRMS (EI, 70 eV) m/z (%): 341 (M+, 100), 191

(15), 262 (13), 340 (53), 341(100); HRMS m/z (ESI) calcd for C23H20NO2 ([M+H]+)

341.1425, found 341.1438.

1-Methyl-3-(3-methylbenzyl)-4-phenyl-1-

azaspiro[4.5]deca-3,6,9-triene-2,8-dione (3aj):

Yellow solid; mp: 153.9-159.5 oC(uncorrect); 1H

NMR (400 MHz, CDCl3) : 7.38-7.30 (m, 3H), 7.13-7.10 (m, 3H), 6.99-6.90 (m, 3H),

6.51 (d, J = 9.2 Hz, 2H), 6.42 (d, J = 9.2 Hz, 2H), 3.64 (s, 2H), 2.90 (s, 3H), 2.28 (s,

3H); 13C NMR (100 MHz, CDCl3) : 184.2, 170.6, 150.4, 145.6, 138.1, 138.0, 137.2,

ON O

ON O

133.0, 131.0, 129.4, 129.2, 128.4, 128.3(2C), 127.1, 125.4, 67.6, 30.7, 26.1, 21.4; IR

(KBr, cm-1): 1662, 1684; LRMS (EI, 70 eV) m/z (%): 355 (M+, 100), 326 (6), 262

(12); HRMS m/z (ESI) calcd for C24H22NO2 ([M+H]+) 356.1645, found 356.1658.

3-(3,5-Dimethylbenzyl)-1-methyl-4-phenyl-1-

azaspiro[4.5]deca-3,6,9-triene-2,8-dione (3ak):

Yellow solid; mp: 161.3-165.8 oC (uncorrect); 1H

NMR (400MHz, CDCl3) : 7.34-7.31 (m, 3H), 7.10 (d, J = 6.4 Hz, 2H), 6.81 (s, 1H),

6.72 (s, 2H), 6.51 (d, J = 9.2 Hz, 2H), 6.42 (d, J = 10.0 Hz, 2H), 3.61 (s, 2H), 2.90 (s,

3H), 2.23 (s, 6H); 13C NMR (100 MHz, CDCl3) : 184.2, 170.6, 150.5, 145.7, 138.0,

137.9, 137.3, 133.0, 131.0, 129.2, 128.4, 128.3, 128.0, 126.4, 67.6, 30.6, 26.1, 21.2;

IR (KBr, cm-1): 1663, 1685; LRMS (EI, 70 eV) m/z (%): 369 (M+, 100), 354 (7), 262

(13); HRMS m/z (ESI) calcd for C25H24NO2 ([M+H]+) 370.1802, found 370.1819.

1-Benzyl-3-cyclohexyl-4-phenyl-1-azaspiro[4.5]deca-3,6,9-

triene-2,8-dione (3ba):

Yellow oil; 1H NMR (400 MHz, CDCl3) : 7.23-7.18 (m,

8H), 6.90 (d, J = 6.8 Hz, 2H), 6.24 (d, J = 9.6 Hz, 2H), 6.08

(d, J = 9.6 Hz, 2H), 4.46 (s, 2H), 2.38 (t, J = 10.4 Hz, 1H), 1.65-1.54 (m, 7H), 1.20-

1.10 (m, 3H); 13C NMR (100 MHz, CDCl3) : 184.4, 170.5, 149.0, 146.2, 141.9,

137.8, 132.0, 131.3, 128.9, 128.8, 128.6, 128.5, 128.1, 127.7, 67.7, 44.7, 37.0, 30.5,

26.3, 25.6; IR (KBr, cm-1): 1670, 1681; LRMS (EI, 70 eV) m/z (%): 409 (M+, 100),

207 (25), 91 (91); HRMS m/z (ESI) calcd for C28H28NO2 ([M+H]+) 410.2115, found

410.2116.

ON O

ON O

1-Allyl-3-cyclohexyl-4-phenyl-1-azaspiro[4.5]deca-3,6,9-

triene-2,8-dione (3ca):

Yellow oil; 1H NMR (400 MHz, CDCl3) : 7.33-7.27 (m,

3H), 7.03 (d, J = 6.4 Hz, 2H), 6.51 (d, J = 9.6 Hz, 2H), 6.32

(d, J = 9.6 Hz, 2H), 5.83-5.71 (m, 1H), 5.13 (d, J = 13.2 Hz, 2H), 3.93 (d, J = 5.6 Hz,

2H), 2.43 (t, J = 11.6 Hz, 1H), 1.71-1.56 (m, 7H), 1.26-1.16 (m, 3H); 13C NMR (100

MHz, CDCl3) : 184.5, 170.3, 149.0, 146.2, 142.1, 133.4, 132.3, 131.4, 128.9, 128.6,

128.1, 118.4, 67.7, 43.6, 36.9, 30.4, 26.2, 25.5; IR (KBr, cm-1): 1666, 1681; LRMS

(EI, 70 eV) m/z (%): 359 (M+, 100), 318 (15), 290 (14); HRMS m/z (ESI) calcd for

C24H26NO2 ([M+H]+) 360.1958, found 360.1956.

3-Cyclohexyl-1,6-dimethyl-4-phenyl-1-azaspiro[4.5]deca-

3,6,9-triene-2,8-dione (3ea):

Yellow oil; 1H NMR (400 MHz, CDCl3) : 7.34 (s, 3H),

7.04 (d, J = 6.0 Hz, 2H), 6.46 (d, J = 10.0 Hz, 1H), 6.38 (d, J = 10.0 Hz, 1H), 6.28 (s,

1H), 2.78 (s, 3H), 2.50 (t, J = 11.6 Hz, 1H), 1.82-1.45 (m, 10H), 1.26-1.17 (m, 3H);

13C NMR (100 MHz, CDCl3) : 184.9, 170.8, 153.8, 148.5, 146.0, 142.6, 132.3, 131.7,

131.3, 128.9, 128.3, 128.0, 69.4, 36.8, 30.3, 30.1, 26.1, 25.4 (2C), 17.4; IR (KBr, cm-

1): 1660, 1684; LRMS (EI, 70 eV) m/z (%): 347 (M+, 90), 292 (17), 332 (8), 346 (100);

HRMS m/z (ESI) calcd for C23H26NO2 ([M+H]+) 348.1958, found 348.1972.

3-Cyclohexyl-1-methyl-4,6-diphenyl-1-azaspiro[4.5]deca-

3,6,9-triene-2,8-dione (3fa):

Yellow solid; mp 153.3-155.2oC (uncorrect); 1H NMR

ON O

ON O

ON O

Ph

(400 MHz, CDCl3) : 7.41-7.40 (d, J = 4.0 Hz, 1H), 7.35-7.32 (m, 3H), 7.26 (d, J =

8.0 Hz, 2H), 7.18 (d, J = 8.0 Hz, 2H), 6.92 (d, J = 8 Hz, 2H), 6.53 (s, 1H), 6.49 (d, J =

8.0 Hz, 1H), 6.45 (d, J = 12.0 Hz, 1H), 2.82 (s, 3H), 2.47-2.41 (m, 1H), 1.88-1.54 (m,

7H), 1.45-1.13 (m, 3H); 13C NMR (125 MHz, CDCl3) : 184.3, 170.7, 154.2, 148.8,

147.7, 142.6, 136.0, 132.3, 131.5, 131.3, 130.1, 129.0, 128.6, 128.4, 128.2, 127.1,

69.0, 36.8, 29.9, 29.5, 26.1, 25.7, 25.1; IR (KBr, cm-1): 1649, 1686; LRMS (EI, 70 eV)

m/z (%): 409 (M+, 100), 408 (98), 354 (9); HRMS m/z (ESI) calcd for C28H28NO2

([M+H]+) 410.2155, found 410.2106.

3-Cyclohexyl-1,7-dimethyl-4-phenyl-1-azaspiro[4.5]deca-

3,6,9-triene-2,8-dione (3ga):

Yellow solid; mp 134.2-135.3 oC (uncorrect); 1H NMR

(400 MHz, CDCl3) : 7.32 (s, 3H), 7.02 (d, J = 4.8 Hz, 2H), 6.44 (d, J = 9.6 Hz, 1H),

6.34 (d, J = 9.6 Hz, 1H), 6.26 (s, 1H), 2.87 (s, 3H), 2.42 (t, J = 11.2 Hz, 1H), 1.88 (s,

3H), 1.70-1.42 (m, 7H), 1.25-1.17 (m, 3H); 13C NMR (100 MHz, CDCl3) : 185.0,

170.4, 148.9, 145.8, 141.6, 140.8, 139.9, 132.6, 131.8, 128.7, 128.5, 128.0, 67.8, 36.8,

30.4 (2C), 26.2, 25.9, 25.5, 15.7; IR (KBr, cm-1): 1662, 1686; LRMS (EI, 70 eV) m/z

(%): 347 (M+, 100), 346 (63), 332 (7), 278 (61); HRMS m/z (ESI) calcd for

C23H26NO2 ([M+H]+) 348.1958, found 348.1966.

3-Cyclohexyl-6,9-dimethoxy-1-methyl-4-phenyl-1-

azaspiro[4.5]deca-3,6,9-triene-2,8-dione (3ha):

Yellow solid; mp 170.2-172.6 oC(uncorrect); 1H NMR (400

MHz, CDCl3) : 7.32-7.28 (m, 3H), 6.96-6.95 (m, 2H), 5.67 (s, 1H), 5.08 (s, 1H),

ON O

ON O

MeO

MeO

3.73 (s, 3H), 3.67 (s, 3H), 2.76 (s, 3H) 2.43-2.39 (m, 1H) 1.78-1.61 (m, 7H) 1.26-1.17

(m, 3H); 13C NMR (100 MHz, CDCl3) : 181.3, 171.1, 169.5, 152.8, 149.5, 141.3,

131.8, 128.8, 128.2(2C), 107.8, 105.5, 69.5, 56.3, 55.5, 36.7, 30.6, 30.5, 26.3, 25.6,

25.3; IR (KBr, cm-1): 1700, 1680, 1660, 1649, 1610; LRMS (EI, 70 eV) m/z (%): 393

(M+, 100), 392 (85), 338 (14); HRMS m/z (ESI) calcd for C24H28NO4 ([M+H]+)

394.2013, found 394.2015.

4'-Cyclohexyl-1'-methyl-3'-phenyl-4H-spiro[naphthalene-

1,2'-pyrrole]-4,5'(1'H)-dione (3ia):

Yellow oil; 1H NMR (400 MHz, CDCl3) : 8.07 (d, J = 7.6

Hz, 1H), 7.63 (t, J = 7.6 Hz, 1H), 7.62 (t, J = 7.4 Hz, 1H), 7.48 (t, J = 7.2 Hz, 1H),

7.20-7.12 (m, 4H), 6.58-6.51 (m, 4H), 2.75 (s, 3H), 2.47 (t, J = 11.6 Hz, 1H), 1.78-

1.62 (m, 7H), 1.26-1.18 (m, 3H); 13C NMR (100 MHz, CDCl3) : 183.3, 171.1, 152.1,

146.3, 140.5, 137.7, 133.3, 132.6, 132.5, 131.5, 128.9, 128.5, 128.4, 127.9, 127.1,

125.5, 68.5, 36.7, 30.6, 30.3, 26.2, 25.6, 25.5; IR (KBr, cm-1): 1660, 1685; LRMS (EI,

70 eV) m/z (%): 383 (M+, 100), 382 (89), 328 (8); HRMS m/z (ESI) calcd for

C26H26NO2 ([M+H]+) 384.1958, found 384.1963.

4-(3-Cyclohexyl-1-methyl-2,8-dioxo-1-azaspiro[4.5]deca-

3,6,9-trien-4-yl)benzonitrile (3ja):

Yellow solid; mp: 176.3-177.9 oC(uncorrect); 1H NMR

(400 MHz, CDCl3) : 7.65 (d, J = 8.0 Hz, 2H), 7.20 (d, J =

4.0 Hz, 2H), 6.48 (d, J = 8.0 Hz, 2H), 6.41 (d, J = 8.0 Hz, 2H), 2.89 (s, 3H), 2.42-2.37

(m, 1H), 1.71-1.55 (m, 7H), 1.26-1.17 (m, 3H); 13C NMR (100 MHz, CDCl3) : 183.7,

O

N

O

ON O

NC

169.7, 146.2, 145.2, 143.7, 136.5, 133.3, 132.1, 129.5, 118.0, 113.0, 67.1, 37.1, 30.5,

26.1, 26.0, 25.4; IR (KBr, cm-1): 1688, 1669, 1629; LRMS (EI, 70 eV) m/z (%): 358

(M+, 100), 357 (97), 303 (19); HRMS m/z (ESI) calcd for C23H23N2O2 ([M+H]+)

359.1754, found 359.1771.

3-Cyclohexyl-1-methyl-4-m-tolyl-1-azaspiro[4.5]deca-3,6,9-triene-

2,8-dione (3ka):

Yellow solid; mp 108.3-109.7 oC (uncorrect); 1H NMR

(400 MHz, CDCl3) : 7.20-7.14 (m, 2H), 6.84 (s, 2H), 6.48 (d, J = 9.6 Hz, 2H), 6.38

(d, J = 9.2 Hz, 2H), 2.87 (s, 3H), 1.76-1.55 (m, 7H), 1.26-1.18 (m, 3H); 13C NMR

(100 MHz, CDCl3) : 184.3, 170.5, 148.8, 146.0, 141.8, 137.7, 132.7 131.5, 129.6,

129.0, 128.0, 125.5, 67.3, 36.8, 30.3, 26.2, 25.9, 25.5, 21.4; IR (KBr, cm-1): 1647,

1682; LRMS (EI, 70 eV) m/z (%): 347 (M+, 100), 346 (61), 332 (17); HRMS m/z (ESI)

calcd for C23H26NO2 ([M+H]+) 348.1958, found 348.1972.

3-Cyclohexyl-4-(2-methoxyphenyl)-1-methyl-1-

azaspiro[4.5]deca-3,6,9-triene-2,8-dione (3la):

Yellow solid; mp: 113.3-114.4 oC(uncorrect); 1H NMR

(400 MHz, CDCl3) : 7.30- (t, J = 8.8 Hz, 1H), 6.87-6.81 (m, 3H), 6.57 (d, J = 8.0 Hz,

1H), 6.45 (d, J = 7.6 Hz, 1H), 6.35 (d, J = 8.0 Hz, 1H), 6.21 (d, J = 8.4 Hz, 1H),3.72

(s, 3H), 2.89 (s, 3H), 2.33-2.27 (m, 1H), 1.65-1.47 (m, 4H), 1.26-1.07(m, 4H); 13C

NMR (125 MHz, CDCl3) : 184.6, 170.7, 156.5, 146.9, 146.2, 145.5, 143.1, 132.8,

131.0, 130.6, 130.3, 120.1, 119.9, 110.7, 68.2, 55.0, 37.2, 30.2, 29.7, 26.3, 26.2, 25.7;

ON O

ON O

OMe

IR (KBr, cm-1): 1683, 1666; LRMS (EI, 70 eV) m/z (%): 363 (M+, 60), 338 (100), 308

(12); HRMS m/z (ESI) calcd for C23H26NO3 ([M+H]+) 364.1907, found 364.1923.

3-Cyclohexyl-1-methyl-4-(pyridin-4-yl)-1-

azaspiro[4.5]deca-3,6,9-triene-2,8-dione (3ma):

Yellow solid; mp 175.6-179.7 oC(uncorrect); 1H NMR

(400 MHz, CDCl3) : 8.62 (d, J = 2.8 Hz, 2H), 7.01 (d, J = 4.0 Hz, 2H), 6.48-6.40 (m,

4H), 2.89 (s, 3H), 2.42 (t, J = 11.6 Hz, 1H), 1.71-1.57 (m, 3H), 1.26-1.18 (m, 3H); 13C

NMR (100 MHz, CDCl3) : 183.6, 169.6, 149.8, 145.3, 145.0, 143.6, 140.0, 133.3,

123.3, 66.9, 37.0, 30.4, 26.1, 26.0, 25.4; IR (KBr, cm-1): 1640, 1680; LRMS (EI, 70

eV) m/z (%): 334 (M+, 100), 333 (65), 279 (16); HRMS m/z (ESI) calcd for

C21H23N2O2 ([M+H]+) 335.1754, found 335.1763.

3-Cyclohexyl-1-methyl-4-(thiophen-2-yl)-1-

azaspiro[4.5]deca-3,6,9-triene-2,8-dione (3na):

Yellow oil; 1H NMR (400 MHz, CDCl3) : 7.38 (t, J =

2.0 Hz, 1H), 7.04 (s, 2H), 6.51-6.44 (m, 4H), 2.87-2.82 (m, 4H), 2.08-2.02 (m, 2H),

1.82-1.80 (m, 2H), 1.68-1.60 (m, 4H), 1.31-1.26 (m, 2H); 13C NMR (100 MHz,

CDCl3) : 184.4, 169.9, 146.2, 141.8, 141.1, 133.3, 132.1, 128.1, 127.7, 127.4, 66.4,

37.4, 29.7, 26.3, 25.6;IR (KBr, cm-1): 1680, 1669; LRMS (EI, 70 eV) m/z (%): 339

(M+, 100), 281 (29), 207 (78); HRMS m/z (ESI) calcd for C20H22NO2S ([M+H]+)

340.1371, found 340.1376.

1-(cyclohexyloxy)-2,2,6,6-tetramethylpiperidine (4):

NO

ON O

N

ON O

S

Yellow oil; 1H NMR (400 MHz, CDCl3) : 3.65-3.53 (m, 1H), 2.12-1.98 (m, 2H),

1.80-1.66 (m, 2H), 1.50-1.46 (m, 4H), 1.31-1.06 (m, 19H); 13C NMR (100 MHz,

CDCl3) : 81.7, 59.6, 40.2, 32.9, 25.9, 25.1, 17.3; LRMS (EI, 70 eV) m/z (%): 239

(M+, 100), 225 (29), 142 (59); HRMS m/z (ESI) calcd for C15H30NO ([M+H]+)

240.2322, found 240.2329.

3-Cyclohexyl-1-methyl-4-phenyl-1-azaspiro[4.5]deca-

3,6,9-triene-2,8-dione (3aa-18O):

Yellow solid; melting point 113.1-120.7oC；1H NMR

(400 MHz, CDCl3) : 7.41-7.29 (m, 3H), 7.05 (d, J = 7.2 Hz, 2H), 6.48 (d, J = 9.6 Hz,

2H), 6.37 (d, J = 9.2 Hz, 2H), 2.88 (s, 3H), 2.50-2.39 (m, 1H), 1.78-1.66 (m, 4H),

1.65-1.53 (m, 3H), 1.23-1.12 (m, 2H); 13C NMR (400 MHz, CDCl3) : 184.21, 184.17,

170.5, 148.6, 146.0, 142.2, 132.88, 131.6, 128.9, 128.5, 128.2, 67.4, 36.9, 30.4, 26.3,

25.9, 25.6; LRMS (EI, 70 eV) m/z (%): 335 (M+, 15), 334 (34), 333 (98), 332 (100),

290 (8), 278 (17); HRMS m/z (ESI) calcd for C22H24NO2 ([M+H]+) 336.1844, found

336.1849.

18ON O

(D) Spectra

3-Cyclohexyl-1-methyl-4-phenyl-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione (3aa)

1-Methyl-3-(methylcyclohexyl)-4-phenyl-1-azaspiro[4.5]deca-3,6,9-triene-2,8-

dione and 3-(Cyclohexylmethyl)-1-methyl-4-phenyl-1-azaspiro[4.5]deca-3,6,9-

triene-2,8-dione (3ab)

3-Cyclopentyl-1-methyl-4-phenyl-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione (3ac)

3-Cycloheptyl-1-methyl-4-phenyl-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione

(3ad)

3-Cyclooctyl-1-methyl-4-phenyl-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione (3ae)

3-Hexanyl-1-methyl-4-phenyl-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione (3af)

1-Methyl-4-phenyl-3-(1-phenylethyl)-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione

(3ag)

3-Benzyl-1-methyl-4-phenyl-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione (3ai)

1-Methyl-3-(3-methylbenzyl)-4-phenyl-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione

(3aj)

3-(3,5-Dimethylbenzyl)-1-methyl-4-phenyl-1-azaspiro[4.5]deca-3,6,9-triene-2,8-

dione (3ak)

1-benzyl-3-cyclohexyl-4-phenyl-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione (3ca)

1-Allyl-3-cyclohexyl-4-phenyl-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione (3da)

3-Cyclohexyl-1,6-dimethyl-4-phenyl-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione

(3ea)

3-Cyclohexyl-1-methyl-4,6-diphenyl-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione

(3fa)

3-Cyclohexyl-1,7-dimethyl-4-phenyl-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione

(3ga)

3-Cyclohexyl-6,9-dimethoxy-1-methyl-4-phenyl-1-azaspiro[4.5]deca-3,6,9-triene-

2,8-dione (3ha)

4'-Cyclohexyl-1'-methyl-3'-phenyl-4H-spiro[naphthalene-1,2'-pyrrole]-4,5'(1'H)-

dione (3ia)

4-(3-cyclohexyl-1-methyl-2,8-dioxo-1-azaspiro[4.5]deca-3,6,9-trien-4-

yl)benzonitrile (3ja)

3-Cyclohexyl-1-methyl-4-m-tolyl-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione (3ka)

3-Cyclohexyl-4-(2-methoxyphenyl)-1-methyl-1-azaspiro[4.5]deca-3,6,9-triene-2,8-

dione (3la)

3-Cyclohexyl-1-methyl-4-(pyridin-4-yl)-1-azaspiro[4.5]deca-3,6,9-triene-2,8-

dione (3ma)

3-Cyclohexyl-1-methyl-4-(thiophen-2-yl)-1-azaspiro[4.5]deca-3,6,9-triene-2,8-

dione (3na)

1-(Cyclohexyloxy)-2,2,6,6-tetramethylpiperidine (4)

3-Cyclohexyl-1-methyl-4-phenyl-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione (3aa-18O)