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Synthesis and Characterizationof New Chalcone Derivativesfrom cis-Bicyclo[3.2.0]hept-2-en-6-oneMustafa Ceylan a & Esra Fındık a

a Faculty of Arts and Sciences, Department ofChemistry, Gaziosmanpasa University , Tokat, TurkeyPublished online: 25 Feb 2009.

To cite this article: Mustafa Ceylan & Esra Fındık (2009) Synthesis andCharacterization of New Chalcone Derivatives from cis-Bicyclo[3.2.0]hept-2-en-6-one, Synthetic Communications: An International Journal for Rapid Communication ofSynthetic Organic Chemistry, 39:6, 1046-1054, DOI: 10.1080/00397910802474974

To link to this article: http://dx.doi.org/10.1080/00397910802474974

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Synthesis and Characterization ofNew Chalcone Derivatives fromcis-Bicyclo[3.2.0]hept-2-en-6-one

Mustafa Ceylan and Esra FındıkFaculty of Arts and Sciences, Department of Chemistry,

Gaziosmanpasa University, Tokat, Turkey

Abstract: A series of chalcone derivatives (3a–k) were prepared via the reaction ofcis-bicyclo[3.2.0]hept-2-en-6-one (1) with the respective arylaldehydes (2a–k) andwere then characterized by Fourier transform infrared (FT-IR), 1H NMR,13C NMR, and elemental analyses.

Keywords: cis-Bicyclo[3.2.0]hept-2-en-6-one, chalcone, Claisen–Schmidtcondensation

a,b-Unsaturated ketones, especially 1,3-diarylprop-2-en-1-ones,commonly known as chalcones, have received considerable attention inmedicinal chemistry.[1] Chalcones are natural or synthetic compoundsbelonging to the flavonoid family,[2] and they are important compoundsnot only because of their biological properties but also because they serveas important intermediates for the synthesis of a large number of hetero-cyclic systems.[1] They are also very important as a Michael acceptor inorganic syntheses.[3]

Moreover, chalcones have been extensively studied[4] for their broadspectrum of biological activities, including bacteriostatic, fungistatic, anti-parasitic, cardiovascular, antitumor,[5] anticancer,[6,7] anti-inflammatory,[8,9]

antileishmanial,[10] antitubercular,[11] and antifung[12] activities. In fact, the

Received June 25, 2008.Address correspondence to Mustafa Ceylan, Faculty of Arts and Sciences,

Department of Chemistry, Gaziosmanpasa University, 60250 Tokat, Turkey.E-mail: mceylan@gop.edu.tr

Synthetic Communications1, 39: 1046–1054, 2009

Copyright # Taylor & Francis Group, LLC

ISSN: 0039-7911 print=1532-2432 online

DOI: 10.1080/00397910802474974

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pharmacological properties of chalcones are due to the presence of botha,b-unsaturation[13] and an aromatic ring. Constant interest in chalconeshas resulted in syntheses of new derivatives using both classical[14,15] andcombinatorial techniques.[16]

In this study, a series of new chalcone-like compounds (3a–k) weresynthesized by the reaction of cis-bicyclo[3.2.0]hept-2-en-6-one withappropriately aldehyde derivatives (2a–k).

The general synthetic strategy employed to prepare the chalconederivatives (3a–k) based on Claisen–Schmidt condensation, which wasreported previously.[17] As shown in Scheme 1 and Table 1, new chalconederivatives (3a–k) were prepared by base-catalyzed condensation of cis-bicyclo[3.2.0]hept-2-en-6-one with substituted benzaldehydes, furfural,thiophene-2-carbaldehyde, and 1H-pyrrole-2-carbaldehyde in yields of89–98% (Scheme 1). The structures of all the 11 chalcone derivatives(3a–k) synthesized in this study were established on the basis of infrared(IR), 1H NMR and 13C NMR spectral data, and elemental analyses.

1H NMR spectrum of all chalcone derivatives show AB system atd¼ 2.76–2.45 ppm arising from H3 protons, the AB system of H2 and H6protons at d¼ 4.50–3.80 ppm, and the signal of b proton at d¼ 6.80 ppmas singlet. Fourteen lines in 13C NMR chalcone derivative spectrum arein agreement with the proposed structures.

EXPERIMENTAL

Instruments

Melting points of the compounds were measured using an Electrothermal9100 apparatus. IR spectrums (KBr or liquid) were taken by a JascoFT=IR-430 IR spectrophotometer. 1H and 13C NMR spectra were rec-orded using a Brucker Avance III instrument using tetramethylsilane(TMS, d 0.00) for 1H NMR and CDCl3 (d 77.0) for 13C NMR spectro-scopy as internal reference standards; J values were given in hertz. Themultiplicities of the signals in the 1H NMR spectra are abbreviated bys (singlet), d (doublet), t (triplet), q (quarted), m (multiplet), br (broad),

Scheme 1. Synthesis of chalcone derivatives 3a–k.

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Table 1. Synthesized new chalcone derivatives

Entry Ketones Ar Products Isolated yield (%)

1 1 Ph 95

2 1 4-BrPh 97

3 1 4-ClPh 98

4 1 4-CH3OPh 95

5 1 4-CH3Ph 93

6 1 3-CH3Ph 91

7 1 3-ClPh 93

8 1 3-BrPh 94

9 1 Thienyl 95

(Continued )

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and combinations thereof. Elemental analyses were obtained from aLECO CHNS 932 elemental analyzer.

Reagent

Bicyclo[3.2.0]hept-2-en-6-one and aldehyde derivatives were commercialproducts with the highest reagent grade.

General Procedure for Synthesis (3a–k)

A solution of NaOH (2.3 mmol) in water was added to a vigorouslystirring solution of the mixture of cis-bicyclo[3.2.0]hept-2-en-6-one(2.3 mmol) and benzaldehyde derivative (2.3 mmol) in ethanol (10 ml).The resultant solution was then stirred at room temperature for 3 h.The reaction mixture was diluted with EtOAc, neutralized with HClsolution (10%), and then washed with water. The organic layer was driedover anhydrous Na2SO4, filtered, and evaporated. Solid compounds wererecrystallized in EtOAc=n-hexane (1:9).

Data

7-Benzylidenebicyclo[3.2.0]hept-2-en-6-one (3a)

Viscous oil, bp 188–190 �C=760 torr; 1H NMR (400 MHz, CDCl3) d¼ 7.56–7.55 (m, 2H, ArH), 7.38–7.37 (m, 3H, ArH), 6.83 (s, 1H), 6.01–5.99 (m, 1H),5.83–5.82 (m, 1H), 4.36 (m, 1H), 3.88–3.85 (m, 1H), 2.78–2.76 (m,1H), 2.58–2.44 (m, 1H). 13C NMR (100 MHz, CDCl3): d¼ 203.7,

Table 1. Continued

Entry Ketones Ar Products Isolated yield (%)

10 1 Furyl 92

11 1 Pyrrol 89

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149.41, 134.25, 133.27, 129.99, 129.88 (2C), 129.0 (2C), 128.86, 124.17,60.56, 49.68, 34.84. IR (liquid): 3419, 3237, 3054, 2916, 2851, 1742,1640, 1448, 1241, 1162, 1101, 1089, 895, 751, 674, 625, 466, 413. Anal.calcd. for C14H12O:C, 85.68; H, 6.16, Found: C, 85.48; H, 5.96.

7-(4-Brombenzylidene)bicyclo[3.2.0]hept-2-en-6-one (3b)

Yellowish crystals, mp 95–97 �C. 1H NMR (400 MHz, CDCl3): d¼ 7.52(d, J¼ 8.4 Hz, 2H), 7.42 (d, J¼ 8.4 Hz, 2H), 6.77 (s, 1H), 5.98–5.96 (m,1H), 5.87–5.86 (m, 1H), 4.35–4.34 (m, 1H), 3.92–3.88 (m,1H), 2.78 (bd,J¼ 17.6 Hz, 1H), 2.58 (dd, J¼ 17.6, 10.4 Hz, 1H). 13CNMR (100 MHz,CDCl3): d¼ 203.61, 149.91, 133.68, 133.16, 132.25 (2 C), 131.13 (2 C),128.36, 124.34, 122.88, 60.84, 49.61, 34.77. IR (KBr): 3444, 3057,301, 2918, 2899, 1736, 1636, 1484, 1399, 1154, 1069, 906, 811, 717, 533,472. Anal. calcd. for C14H11BrO: C, 61.11; H, 4.03, Found: C, 60.98;H, 4.16.

7-(4-Chlorobenzylidene)bicyclo[3.2.0]hept-2-en-6-one (3c)

Yellowish crystals, mp 92–94 �C. 1H NMR (400 MHz, CDCl3): d¼ 7.51(d, J¼ 8.4 Hz, 2H), 7.38 (d, J¼ 8.4 Hz, 2H), 6.80 (d, J¼ 2 Hz, 1H),6.00–5.97 (m, 1H), 5.89–5.87 (m, 1H), 4.37–4.36 (m, 1H), 3.90 (ddd,J¼ 9, 7, 2 Hz, 1H), 2.82–2.75 (m, 1H), 2.63–2.55 (m, 1H). 13C NMR(100 MHz, CDCl3): d¼ 203.59, 149.79, 135.95, 133.66, 132.76, 130.93(2 C), 129.30 (2 C), 128.40, 122.81, 60.82, 49.58, 34.75. IR (KBr): 3414,3057, 3010, 2965, 2902, 2848, 1736, 1636, 1404, 1234, 1076, 897, 814,720, 535, 474, 406. Anal. calcd. for C14H11ClO: C, 72.89; H, 4.81, Found:C, 72.68; H, 4.49.

7-(4-Methoxybenzylidene)bicyclo[3.2.0]hept-2-en-6-one (3d)

Yellowish crystals, mp 82–84 �C. 1H NMR (400 MHz, CDCl3): d¼ 7.53(d, J¼ 8.6 Hz, 2H), 6.93 (d, J¼ 8.6 Hz, 2H), 6.82 (s, 1H), 6.03–6.02 (m,1H), 5.85–5.83 (m, 1H), 4.33–4.32 (m, 1H), 3.89–3.86 (m, 1H), 3.83 (s,3H, -OCH3), 2.76 (bd, J¼ 17.6 Hz, 1H), 2.55 (dd, J¼ 17.6, 10.4 Hz,1H). 13C NMR (100 MHz, CDCl3): d¼ 203.7, 161.7, 147.06, 133.12,131.65 (2C), 129.03, 126.89, 124.21, 114.55 (2C), 60.4, 55.39, 49.35,34.50. IR (KBr): 3417, 3081, 3041, 2967, 2927, 2853, 1736, 1597, 1510,1307, 1257, 1175, 1023, 824, 708, 544, 493, 406. Anal. calcd. forC15H14O2: C, 79.62; H, 6.24, Found: C, 79.44; H, 6.02.

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7-(4-Methylbenzylidene)bicyclo[3.2.0]hept-2-en-6-one (3e)

Viscous oil, bp 217–219 �C=760 torr; 1H NMR (400 MHz, CDCl3):d¼ 7.44 (d, J¼ 8 Hz, 1H), 7.18 (d, J¼ 8 Hz, 1H), 6.80 (s, 1H), 6.01–5.99 (m, 1H), 5.81–5.79 (m, 1H), 4.31–4.30 (m, 1H), 3.83 (dt, J¼ 7.2,2 Hz, 1H), 2.70 (dd, J¼ 17.2, 2 Hz, 1H), 2.53 (ddd, J¼ 17.2, 10.2, 2 Hz,1H), 2.34 (s, 3H). 13C NMR (100 MHz, CDCl3): d¼ 203.72, 148.42,140.49, 133.10, 131.71, 129.93 (2 C), 129.78 (2 C), 128.78, 124.33, 60.51,49.57, 34.61, 21.53. IR (liquid): 3406, 3050, 3026, 2918, 2852, 1739,1637, 1617, 1511, 1236, 1160, 1109, 1078, 907, 811, 704, 603, 469. Anal.calcd. for C15H14O: C, 85.68; H, 6.71, Found: C, 85.38; H, 6.34.

7-(3-Methylbenzylidene)bicyclo[3.2.0]hept-2-en-6-one (3f)

Viscous oil, bp 213–215 �C=760 torr; 1H NMR (400 MHz, CDCl3):d¼ 7.37 (d, J¼ 7.6 Hz, 1H), 7.39 (s, 1H), 7.26 (t, J¼ 7.6 Hz, 1H), 7.16(d, J¼ 7.6 Hz, 1H), 6.78 (s, 1H), 6.0–5.98 (m, 1H), 5.81–5.79 (m, 1H),4.32–4.31 (m, 1H), 3.82 (dt, J¼ 8, 1.6 Hz, 1H), 2.74 (bd, J¼ 17.2 Hz,1H), 2.53 (ddd, J¼ 17.2, 10.4, 1.6 Hz, 1H), 2.34 (s, 3H). 13C NMR(100 MHz, CDCl3): d¼ 203.65, 149.21, 138.58, 134.19, 133.14, 130.88,130.85, 128.96, 128.88, 126.82, 124.38, 60.58, 49.70, 34.67, 21.39. IR(liquid): 3236, 3051, 2949, 2918, 2852, 1745, 1637, 1443, 1288, 1244,1076, 893, 784, 706, 508, 458. Anal. calcd. for C15H14O: C, 85.68; H,6.71, Found: C, 85.54; H, 6.67.

7-(3-Chlorobenzylidene)bicyclo[3.2.0]hept-2-en-6-one (3g)

Viscous oil, bp 220–221 �C=760 torr; 1H NMR (400 MHz, CDCl3):d¼ 7.48 (s, 1H), 7.42–7.39 (m, 1H), 7.30–7.29 (m, 2H), 6.72 (s, 1H),5.96–5.94 (m, 1H), 5.84–5.83 (m, 1H), 4.33–4.32 (m, 1H), 3.87 (dt,J¼ 8.6, 1.2 Hz, 1H), 2.74 (bd, J¼ 17.6 Hz, 1H), 2.55 (ddd, J¼ 17.6,10.4, 1.6 Hz, 1H). 13C NMR (100 MHz, CDCl3): d¼ 203.64, 150.50,136.03, 134.87, 133.67, 130.22, 129.82, 129.43, 128.38, 127.86, 122.76,60.87, 49.66, 34.83. IR (liquid): 3423, 3056, 2920, 2852, 1744, 1639,1563, 1428, 1242, 1160, 1080, 915, 784, 684, 540, 435. Anal. calcd. forC14H11ClO: C, 72.89; H, 4.81, Found: C, 72.61; H, 4.64.

7-(3-Brombenzylidene)bicyclo[3.2.0]hept-2-en-6-one (3h)

Viscous oil, bp 205–207 �C=760 torr;1HNMR (400 MHz, CDCl3):d¼ 7.65 (s, 1H), 7.46 (d, J¼ 7.6 Hz, 1H), 7.29–7.21 (m, 2H), 6.71

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(s, 1H), 5.97–5.95 (m, 1H), 5.79–5.76 (m, 1H), 4.34–4.33 (m, 1H), 3.87(dt, J¼ 8.4, 1.2 Hz, 1H), 2.75 (d, J¼ 17.2 Hz, 1H), 2.55 (ddd, J¼ 17.2,9.2, 1.2 Hz, 1H). 13C NMR (100 MHz, CDCl3): d¼ 203.6, 150.53,136.32, 133.70, 132.72, 132.42, 130.49, 128.38, 128.24, 123.04, 122.52,60.90, 49.66, 34.84. IR (liquid): 3486, 3236, 3056, 3016, 2918, 2852,1742, 1638, 1161, 1074, 910, 781, 616. Anal. calcd. for C14H11BrO: C,61.11; H, 4.03, Found: C, 61.00; H, 3.87.

7-(Thiophen-2-ylmethylene)bicyclo[3.2.0]hept-2-en-6-one (3i)

Yellowish crystals, mp 62–64 �C. 1H NMR (400 MHz, CDCl3): d¼ 7.46(d, J¼ 4.4 Hz, 1H), 7.26 (d, J¼ 3.2 Hz, 1H), 7.08–7.05 (m, 2H), 6.07(dd, J¼ 5.4, 2 Hz, 1H), 5.82 (dd, J¼ 5.4, 2 Hz, 1H), 4.23–4.22 (m, 1H),3.80 (ddd, J¼ 8.4, 7, 2 Hz, 1H), 2.72 (bd, J¼ 17.2 Hz, 1H), 2.50 (ddd,J¼ 17.2, 10.4, 2 Hz, 1H). 13C NMR (100 MHz, CDCl3): d¼ 202.88,147.28, 138.31, 133.23, 132.81, 130.01, 128.69, 128.17, 117.33, 59.82,49.08, 34.45. IR (KBr): 3417, 3086, 3072, 2945, 2911, 1725, 1619, 1415,1231, 1107, 1081, 923, 861, 709, 580, 471, 404. Anal. calcd. for C12 H10

OS: C, 71.25; H, 4.98; S, 15.85, Found: C, 70.96; H, 4.76; S, 15.64.

7-(Furan-2-ylmethylene)bicyclo[3.2.0]hept-2-en-6-one (3j)

Orange crystals, mp 52–54 �C. 1H NMR (400 MHz, CDCl3): d¼ 7.55 (s,1H), 6.64–6.63 (m, 2H), 6.48–6.46 (m, 1H), 5.96 (dd, J¼ 5.2, 2 Hz, 1H),5.77 (dd, J¼ 5.2, 2 Hz, 1H), 4.29–4.28 (m, 1H), 3.79 (ddd, J¼ 8.6, 7,1.6 Hz, 1H), 2.70 (bd, J¼ 17.2 Hz, 1H), 2.52 (ddd, J¼ 17.2, 10.4,1.6 Hz, 1H). 13C NMR (100 MHz, CDCl3): d¼ 203.34, 150.96, 146.98,145.44, 132.27, 130.58, 116.28, 112.53, 111.07, 59.82, 49.34, 34.73. IR(KBr): 3412, 3103, 2956, 2913, 2846, 1728, 1637, 1617, 1474, 1267,1232, 1133, 754, 702, 594, 466, 414. Anal. calcd. for C12H10O2: C,77.40; H, 5.41, Found: C, 77.42; H, 5.26.

7-((1H-pyrrol-2-yl)methylene)bicyclo[3.2.0]hept-2-en-6-one (3k)

Green crystals, mp 141–144 �C. 1H NMR (400 MHz, CDCl3): d¼ 11.37(s, 1H, -NH), 7.09–7.08 (d, J¼ 1.2 Hz, 1H), 6.72–6.69 (m, 2H), 6.25 (s,1H), 6.06–6.04 (m, 1H), 5.79–5.74 (m, 1H), 4.17 (m, 1H), 3.80–3.75 (m,1H), 2.53–2.40 (m, 2H). 13C NMR (100 MHz, CDCl3): d¼ 201.96,142.83, 132.52, 130.22, 127.49, 124.20, 115.02, 114.14, 111.62, 59.22,48.42, 33.94. IR (KBr): 3477, 3415, 3241, 3101, 2899, 2838, 1698, 1615,1430, 1336, 1160, 1029, 984, 891, 741, 613, 418, 406. Anal. calcd. forC12H11NO: C, 77.81; H, 5.99; N, 7.56, Found: C, 77.62; H, 6.15.

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ACKNOWLEDGMENT

The authors are indebted to the Gaziosmanpasa University ScientificResearch Projects Committee (BAP-2005=30) and the Scientific andTechnical Research Council of Turkey (TUBITAK-BIDEP) for financialsupport.

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