A new Synthesis of 3-arylpropenoic acids and 5-phenyl-2,4- pentadienoic acid from 4-acetyl-3-arylsydnones and arylaldehydes

Organic Communications

Volumn 2, Issue 2, 2009, Pages 42-48

  Sanyal, R ^a   Badami, Bharati V ^a  

^a KARNATAK UNIVERSITY   (India)

Author keywords

3 Aryl (4 cinnamoyl)sydnones; 3 Arylpropenoic acids; 5 Phenyl 2,4 pentadienoic acid

Indexed keywords

EID: 77951543930     PISSN: None     EISSN: 13076175     Source Type: Journal    
DOI: None     Document Type: Article

References (14)

1. Veverkova, E.; Pacherova, E.; Toma, S. Examination of the Perkin reaction under microwave irradiation. Chem. Pap. - Chem. Zvesti, 1999, 53, 257-290.
2. Narasimhan, B.; Belsare, D.; Pharande, D.; Mourya, V.; Dhake, A. Esters, amides and substituted derivatives of cinnamic acid: synthesis, antimicrobial activity and QSAR investigations. Eur. J. Med. Chem. 2004, 39, 827-834.
3. Adisakwattana, S.; Sookkongwaree, K.; Roengsumran, S.; Petsom, A.; Ngamrojnavanich, N.; Chavasiri, W.; Deesamer, S.; Yibchok-Anun, S. Structure-activity relationships of trans-cinnamic acid derivatives on alpha-glucosidase inhibition. Bioorg. Med. Chem. Lett. 2004, 14, 2893-2896.
4. Monien, B. H.; Henry, B.L.; Raghuraman, A.; Hindle, M.; Desai U.R. Novel chemo-enzymatic oligomers of cinnamic acids as direct and indirect inhibitors of coagulation proteinases. Bioorg. Med. Chem. 2006, 14, 7988-7998.
5. Werbel, L. M.; Headen, N.; Elslager E. F. Derivatives of 5-phenyl-2,4-pentadienoic acid as potential antimalarial agents. J. Med. Chem. 1968, 11, 1073-1074.
6. Hosamani, C. K.; Badami, B. V. Michael addition of ethyl acetoacetate to alpha-beta unsaturated ketones of 3-arylsydnones: Synthesis and antimicrobial activity of 3-(4-cinnamoyl), 4-(6 '-carbethoxy-5 '-aryl-cyclohex-2 '-en-1 '-one-3 '-yl) and 4-(1 ',2 ',4 ',5 '-tetrahydro-4 '-aryl-indazolin-3 '-one-6 '-yl)-arylsydnones. Indian J. Heterocycl. Chem. 1998, 7, 245-248.
7. Kavali, J. R.; Badami, B. V. 1,5-Benzodiazepine derivatives of 3-arylsydnones: synthesis and antimicrobial activity of 3-aryl-4-[2 '-aryl-2 ',4 ',6 ',7 '-tetrahydro-(1 ' H)-1 ',5 '-benzodiazepine-4 '-yl]sydnones. Farmaco, 2000, 55, 406-409.
8. Greco C. V.; Tobias J.; Kier L. B. Acylation of 3-phenylsydnone with carboxylic acids and phosphorus pentoxide. J. Heterocycl. Chem. 1967, 4, 160-162.
9. Tikare R. K.; Upadhya K. G.; Badami B. V.; Puranik, G. S. Synthesis and biological-activity of 4-substituted 3-arylsydnones - 3-aryl-4-(benzofuran-2'-carbonyl)-, 3-aryl-4-(6'-imidazo[2,1-b]-thiazolyl)-and 3-aryl-4-[2'-imidazo-[1,2-a]pyridyl)-sydnone. Ind. J. Chem. 1984, 23B, 798-800.
10. Baker, W.; Ollis, W. D. Mesoionic compounds. Quart. Rev. (London), 1957, 11, 15-29.
11. Thamotharan, S.; Parthasarathi, V.; Sanyal, R.; Badami, B.; Linden A. 3-(4-Methoxyphenyl)-4-(5-phenyl-2,4-pentadienoyl)sydnone. Acta Cryst. 2003, E59, o894-896.
12. Patel, B.A.; Dickerson, J.E.; Heck, R.F. Palladium-catalyzed arylation of conjugated dienes. J. Org. Chem. 1978, 43, 5018-5020.
13. Clarke, H.T. A handbook of organic qualitative and quantitative analysis, Edward Arnold, London, 1960, p.143.
14. Bellassoued, M.; Lensen, N.; Bakasse M.; Mouelhi, S. Two-Carbon Homologation of Aldehydes via Silyl Ketene Acetals: A New Stereoselective Approach to (E)-Alkenoic Acids. J. Org. Chem. 1998, 63, 8785-8789.