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Tetrahedron Letters Vol. 54, Issue 40, 2013
Contents
COMMUNICATIONS
Synthesis, X-ray analysis and photophysical properties of a new N-containing pentacyclic helicene pp 5421–5425
Mourad Ben Braiek, Faouzi Aloui, Souad Moussa, Moncef Tounsi, Jérome Marrot, Béchir Ben Hassine*
A photolabile protection strategy for terminal alkynes pp 5426–5429
Tina A. Gschneidtner, Kasper Moth-Poulsen*
T3P�-promoted Kabachnik–Fields reaction: an efficient synthesis of a-aminophosphonates pp 5430–5433
Mátyás Milen, Péter Ábrányi-Balogh, András Dancsó, Dávid Frigyes, László Pongó, György Keglevich*
26°C, 5 minT3P
EtOAcAr1 CHO Ar2 NH2+ + P(OEt)3
HNAr2
Ar1 P(O)(OEt)280−96%
Ar1 = 4-MeC6H4, 4-FC6H4, 4-ClC6H4, 4-O2NC6H4, 4-F3CC6H4, 4-MeOC6H4, 4-BnOC6H4, 3-NCC6H4, 1-naphthylAr2 = Ph, 4-MeC6H4, 4-PhC6H4, 4-FC6H4, 4-ClC6H4, 4-BrC6H4, 4-O2NC6H4, 4-EtO2CC6H4, 4-MeOC6H4,
3,4-(MeO)2C6H3, 2-MeSC6H4, 2-Ph(OC)C6H4, 3-PhOC6H4, 3-F3CC6H4, 3-F3COC6H4, 1-naphthyl
5411
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One pot four-component reaction for the efficient synthesis of spiro[indoline-3,40-pyrano[2,3-c]pyrazole]-30-carboxylate derivatives
pp 5434–5440
Suman Pal, Md. Nasim Khan, Shaik Karamthulla, Sk Jahir Abbas, Lokman H. Choudhury*
N
O
OCN
R3
PhHNNH2
COOR4R4OOC
R2
Et3N, EtOH,rt
O
R3
H2N NNH
NO
COOR4
R2
R1
R1
2C-C, 2C-N, 1C-O bond formation
H2NNH2.H2O
O
R3
H2N NN
NO COOR4
R2R1
Ph
Synthesis and dynamic study of new ortho-(alkylchalcogen)acetanilide atropisomers. A second lookat the hydrolysis of quaternary 2-methylbenzazol-3-ium salts
pp 5441–5444
Susana S. Ramos, Lucinda V. Reis, Renato E. F. Boto, Paulo F. Santos, Paulo Almeida*
Experimental temperature dependence of 1H NMR | Computer line shape simulation
I
X = O, S, Se; R = Et, Hex
N
XR
N
X
Studies on the synthesis and biosynthesis of the fungal alkaloid necatorone pp 5445–5447
Jörn Carstens, Markus R. Heinrich*, Wolfgang Steglich*
NO
CO2Me
N
3-aminotyrosine
NH2
HNHO
CO2H
CO2H
F
NH2
NH2
HO
CO2H
CO2Me
NH2
MeO
N
Cu-mediated 1,3-dipolar cycloaddition of azomethine ylides with dipolarophiles: a faster access to spirooxindolesof potential pharmacological interest
pp 5448–5452
Shambhu Nath Singh, Sridhar Regati, Abir Kumar Paul, Mohosin Layek, Sarva Jayaprakash, K. Venkateshwara Reddy,Girdhar Singh Deora, Soumita Mukherjee, Manojit Pal*
NH
O
OH
+N
O
O O R3N
NO
R3OC
R1
R1
R2
R2CuI
MeCN80-85 oC
12 examples; 75-92% yieldCu-mediated three-component reaction afforded novel spirooxindoles for the potential inhibition of PDE4.
5412 Contents / Tetrahedron Letters 54 (2013) 5411–5419
Highly regioselective hydroselenation of inactivated terminal alkynes using diselenide–Ph2P(O)H mixedsystems under visible-light irradiation
pp 5453–5456
Yohsuke Kobiki, Shin-ichi Kawaguchi, Akiya Ogawa*
R (R'Se)2Ph2P(O)H (3a)
+hν (>300 nm)
1 2 4
R SeR'
A cytotoxic dimeric furanoheliangolide from Piptocoma rufescens pp 5457–5460
Yulin Ren, Francisco Jiménez, Ricardo García, Milciades Mejía, Heebyung Chai, Norman R. Farnsworth, Djaja D. Soejarto,A. Douglas Kinghorn*
O
O
O
O
O
O O
O
O
O
O
O
1
A solvent-free amidation of vinylogous esters via direct aziridination pp 5461–5463
Emily C. McLaughlin*, Anuska Shrestha, Madison H. Fletcher, Nathaniel S. Steinauer, Min Kyung Shinn,Sabrina M. Shahid
Reductive iodonio-Claisen rearrangement of iodothiophene diacetates with allylsilanes: formal synthesis of Plavix� pp 5464–5466
Hai Nguyen, Hem Raj Khatri, Jianglong Zhu*
BF3 Et2O, CH2Cl2,-50°C, 2 h
Me3Si
S S
I
97% yield
I(OAc)2
S
N
Cl
CO2Me
Plavix
Contents / Tetrahedron Letters 54 (2013) 5411–5419 5413
Non-phosgene route to unsymmetrical ureas from N-Cbz-a-amino acid amides pp 5467–5469
Ebrahim H. Ghazvini Zadeh*, Nader E. Abo-Dya, Ania C. Sotuyo, Ion Ghiviriga, C. Dennis Hall
BnO
O
NH
R1
O
NHR2
O
NH
R1
OR2HN
RO-
1 2
OHN
R1
O
NR2
HO- RO-
Expanding the scope of the asymmetric anti-aldol addition of chiral N-amino cyclic carbamate hydrazones pp 5470–5472
John D. Knight, Don M. Coltart*
A novel reaction of the ‘Huisgen zwitterion’ with benzofuran-2,3-diones: an efficient strategy for the synthesis ofspirocyclic benzofuran-2-one derivatives
pp 5473–5476
Ze-Dong Wang, Nan Dong, Feng Wang, Xin Li*, Jin-Pei Cheng*
Environmentally benign deprotection of dithioacetals using 30% hydrogen peroxide catalyzedby Fe(acac)3 and sodium iodide
pp 5477–5480
Masayuki Kirihara*, Satoshi Suzuki, Yuki Ishizuka, Kento Yamazaki, Ryoji Matsushima, Takaya Suzuki, Toshiaki Iwai
R R'SS
R R'
OFe(acac)3 (0.1 eq.), NaI (1.0 eq.),30% H2O2 (4.0 eq.)
AcOEt-H2O = 1 : 1, r.t. 99~78%
R1
R3R4
O
O
NN
O
OR5O
+ NN
R5O2C
CO2R5O
R1
R3R4
O
O
CH2Cl2, rt, <10 min
R2R2PPh3
OR5
13 examplesup to 93% yield
5414 Contents / Tetrahedron Letters 54 (2013) 5411–5419
Armillariols A to C from the culture broth of Armillaria sp. pp 5481–5483
Hajime Kobori, Atsushi Sekiya, Nobuhiro Yasuda, Keiichi Noguchi, Tomohiro Suzuki, Jae-Hoon Choi, Hirofumi Hirai,Hirokazu Kawagishi*
Selectivity between N-1 and N-7 nucleosides: regioselective synthesis of BMK-Y101, a potent cdk7 and 9 inhibitor pp 5484–5488
Young-Jong Kim, Soon Ho Kwon, Il Hak Bae, B. Moon Kim*
Bidirectional synthesis of montamine analogs pp 5489–5491
Melanie B. Freitas, Kelly A. Simollardes, Caroline M. Rufo, Chantel N. McLellan, Gabrielle J. Dugas, Leslie E. Lupien,Elizabeth A. Colby Davie*
Regio- and stereoselective synthesis of (Z)-2-Arylsulfanyl allylic alcohols using anhydrous CeCl3 as catalystunder solvent free conditions
pp 5492–5495
Claudio C. Silveira*, Guilherme M. Martins, Samuel R. Mendes
H3CCH3
C2H5S S
CH3HO
H3C
HO
H3C CH3+ Solvent free, 80 °C
CeCl3 (20 mol%)MeNO2 (2 mL/mmol)
CeCl3 (20 mol%)
R-SH0.5 h, 81%3.0 h, 42%
Contents / Tetrahedron Letters 54 (2013) 5411–5419 5415
Palladium-catalyzed aminocarbonylation of aryl iodides using aqueous ammonia pp 5496–5499
Tongyu Xu, Howard Alper*
O O
O P
CH3
H3C
CH3
CH3
Ph
CYTOP® 292
I
+ NH3aqueous
+Pd(OAc)2/CYTOP® 292
CONH2
CO (100 psi )tolueneR R
One-pot solid phase synthesis of (E)-nitroalkenes pp 5500–5504
Lalthazuala Rokhum, Ghanashyam Bez*
R1
O
HR2 NO2+
R1
NO2
R2
CH2Cl2, RT
PPh2/I2/ImH
An efficient protocol for the synthesis of (E)-nitroalkene by sequential one-pot reaction of aldehyde and nitroalkane in the presence of polymer-boundtriphenylphosphine, iodine, and imidazole is described. One-step synthesis of nitroalkenes without using conventional dehydrating reagents, easypurification, and excellent yield of the products are some of the major advantages of the protocol.
DBSA mediated chemoselective synthesis of 2-substituted benzimidazoles in aqueous media pp 5505–5509
Vikash Kumar, Dipratn G. Khandare, Amrita Chatterjee*, Mainak Banerjee*
Microwave assisted efficient aminocarbonylation of N-tosylhydrazones with molybdenum hexacarbonyl and amines pp 5510–5513
K. Penta Rao, Ashok K. Basak, Amancha Raju, Vikas S. Patil, L. Krishnakanth Reddy*
23 examples, 44-82% yield
H2N+
R3Mo(CO) 6, Et4NCl
DBU, DioxaneMicrowave, 140 °C, 45 min
NNHTs
R2
R2
O
R3HN
R1 R1
5416 Contents / Tetrahedron Letters 54 (2013) 5411–5419
Synthesis and spectral properties of ruthenium(II) complexes based on 2,20-bipyridines modified by a perylenechromophore
pp 5514–5517
Koichi Kodama, Akinori Kobayashi, Takuji Hirose*
N
N
N N
N
N RuII
N N
O
O
O
O
R
π-conjugated perylene diimideperylene
Ru(II) + 2,2'-Bipyridine + Perylene chromophores
Synthesis of bifunctional cyclic carbonates from CO2 catalysed by choline-based systems pp 5518–5522
Adérito J. R. Amaral, Jorge F. J. Coelho, Arménio C. Serra*
Lipase from Carica papaya latex presents high enantioselectivity toward the resolution of prodrug (R,S)-2-bromophenylacetic acid octyl ester
pp 5523–5526
Ivanna Rivera, Juan Carlos Mateos, Alain Marty, Georgina Sandoval, Sophie Duquesne*
Pd(OAc)2-catalyzed oxidative carbonylation of aromatics: synthesis of naphthalenecarboxylic acids pp 5527–5531
Alexander R. Elman*
COOHO OO
+COPd(OAc)2,
K2S2O8
Contents / Tetrahedron Letters 54 (2013) 5411–5419 5417
A new route to the synthesis of isoxazoline derivatives from dihydropyran via cycloaddition reaction in ionic liquid pp 5532–5536
Bhaskar Chakraborty*, Chiran Devi SharmaRNHOH
NO H
R1 R2
RR3
12
3
45
[bmim]BF4
[bmim]BF4
R = CH3/C6H5/C6H11/ C6H5CH2/4-OHC6H4/2-OHC6H4
R1 = Ph ; R2 = COOCH3
R1 = R2 = COOCH3
R1 = R2 = COOHR3 = -(CH2)4OHR4 = H ; CH3 ; C6H5
R2R1
OO N
OH
R
OHN+
O-
R1
OHN+
O-
R1 2
C
H2N
R4COOH
H
N
OR1
C
R
H R3
N
O
H
C
HC
R4
O
HO
3
N
R
R1
O
R2
R3
2a
A new approach to the synthesis and 1,3-dipolar cycloadditions of nitrones has been described from 2,3-dihydro-4H-pyran and various hydroxylamines,with electron-deficient alkynes for the synthesis of isoxazoline derivatives. Significant rate acceleration and improved yields of exclusively exoisoxazolines in 1-butyl-3-methylimidazolium based ionic liquids have been observed. Novel isoxazolines may be used as a precursor for the synthesis ofvariety of peptides.
A one-pot, three-component, microwave-promoted synthesis of 2-amino-substituted 7-amino-1,2,4-triazolo[1,5-a][1,3,5]triazines
pp 5537–5540
Svetlana A. Kalinina, Dmitrii V. Kalinin, Anton V. Dolzhenko*
N
N
NN
NN
NH2
NHN
N NH2
NH2
HC(OEt)3
+
N
Nmicrowaves
R1
R2R2
R1
4-CF3-ezetimibe analogs: design, synthesis, and biological evaluation of cholesterol absorption inhibitions pp 5541–5543
Yingle Liu, Jun-Ling Chen, Gai-Hong Wang, Peng Sun, Heyao Huang, Feng-Ling Qing*
NO
F
OH
Ezetimibe
OH
FN
O
F
OH
F
CF3
1a
CF3
93% inhibitionof cholesterol absorpion
73% inhibitionof cholesterol absorpion
OTHER CONTENT
Corrigendum to ‘‘The Michael addition of 1,2-cyclohexanedione to b-nitrostyrenes (I): the synthesis of 3-aryl-5,6-dihydrobenzofuran-7(4H)-ones’’ [Tetrahedron Lett. 54 (2013) 3371–3373]
p 5544
Chad M. Simpkins, David A. Hunt*
5418 Contents / Tetrahedron Letters 54 (2013) 5411–5419
Corrigendum to ‘‘Surprising behavior of NXO-peptides toward the lithium hydroxide solvolysis’’[Tetrahedron Lett. 54 (2013) 3679–3682]
p 5545
Farhan A. Khan*, Constantin Rabong, Ulrich Jordis, Jaywant Phopase*
*Corresponding authorSupplementary data available via ScienceDirect
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Contents / Tetrahedron Letters 54 (2013) 5411–5419 5419