Microwave-assisted convenient synthesis of α,β-unsaturated esters and ketones via aldol-adduct elimination

Helvetica Chimica Acta

Volumn 96, Issue 8, 2013, Pages 1548-1559

  Suman, Pathi ^a   Nageswara Rao, Rayala ^a   China Raju, Bhimapaka ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

1,3 Diketones; Aldol adduct elimination; C,C Bond formation; Esters; Fluorine compounds; Ketones; Microwave irradiation

Indexed keywords

1 ,3-DIKETONES; ALDOL-ADDUCT ELIMINATION; BOND FORMATION; C,C-BOND FORMATION; MICROWAVE-ASSISTED; SYSTEMATIC STUDY; UNSATURATED ESTERS;

ESTERIFICATION; ESTERS; FLUORINE COMPOUNDS; MICROWAVE IRRADIATION;

KETONES;

ESTER; KETONE; PIPERIDINE;

ALDOL REACTION; ARTICLE; CHEMICAL BINDING; CHEMICAL STRUCTURE; ELIMINATION REACTION; MICROWAVE IRRADIATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; ROOM TEMPERATURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 84882249440     PISSN: 0018019X     EISSN: 15222675     Source Type: Journal    
DOI: 10.1002/hlca.201200526     Document Type: Article

References (40)

1. J. Carrillo, A. M. Costa, M. Sidera, J. Vilarrasa, Tetrahedron Lett. 2011, 52, 5153
2. A. M. Heapy, M. A. Brimble, Tetrahedron 2010, 66, 5424
3. J. S. Yadav, U. V. Subha Reddy, B. Anusha, B. V. Subha Reddy, Tetrahedron Lett. 2010, 51, 5529
4. H. Takamura, S. Kikuchi, Y. Nakamura, Y. Yamagami, T. Kishi, I. Kadota, Y. Yamamoto, Org. Lett. 2009, 11, 2531
5. D. Rossi, A. C. Baraglia, M. Serra, O. Azzolina, S. Collina, Molecules 2010, 15, 5938.
6. W. C. Shearouse, C. M. Korte, J. Mack, Green Chem. 2011, 13, 598
7. K. Ando, K. Yamada, Green Chem. 2011, 13, 1143
8. K. Ando, K. Yamada, Tetrahedron Lett. 2010, 51, 3297
9. N. Shimojuh, Y. Imura, K. Moriyama, H. Togo, Tetrahedron 2011, 67, 951.
10. E. Knoevenagel, Chem. Ber. 1904, 37, 4461
11. P. D. Gardner, R. L. Brandon, J. Org. Chem. 1957, 22, 1704.
12. M. V. Pryadeina, O. G. Kuzueva, Y. V. Burgart, V. I. Saloutin, K. A. Lyssenko, M. Y. Antipin, J. Fluorine Chem. 2002, 117, 1
13. S. Zhu, B. Xu, J. Zhang, J. Fluorine Chem. 1995, 74, 167
14. R. A. Khera, M. Hussain, R. Ahmad, A. Saeed, A. Villinger, A. Fischer, P. Langer, J. Fluorine Chem. 2010, 131, 892.
15. B. China Raju, G. Saidachary, J. Ashok Kumar, B. Sridhar, Helv. Chim. Acta 2011, 94, 248.
16. B. China Raju, G. Saidachary, J. Ashok Kumar, Tetrahedron 2012, 68, 6289.
17. B. China Raju, P. Suman, Chem.-Eur. J. 2010, 16, 11840.
18. B. China Raju, R. N. Rao, P. Suman, P. Yogeeswari, D. Sriram, T. B. Shaik, S. V. Kalivendi, Bioorg. Med. Chem. Lett. 2011, 21, 2855
19. B. China Raju, A. K. Tiwari, J. A. Kumar, A. Z. Ali, S. B. Agawane, G. Saidachary, K. Madhusudana, Bioorg. Med. Chem. 2010, 18, 358
20. P. V. Ramachandran, D. Pratihar, G. Garner, B. China Raju, Tetrahedron Lett. 2011, 52, 4985
21. P. Narender, M. Ravinder, P. Sarathi Sadhu, B. China Raju, C. Ramesh, V. J. Rao, Helv. Chim. Acta 2009, 92, 959.
22. A. Gazit, Z. Rappoport, J. Chem. Soc., Perkin Trans 1 1984, 2863.
23. D. Mead, R. Loh, A. E. Asato, R. S. H. Liu, Tetrahedron Lett. 1985, 26, 2873.
24. T. Ishihara, T. Maekawa, T. Ando, Tetrahedron Lett. 1983, 24, 4229
25. D. Zhang, C. Yuan, Eur. J. Org. Chem. 2007, 23, 3916.
26. S. Ikeda, M. Shibuya, N. Kanoh, Y. Iwabuchi, Org. Lett. 2009, 11, 1833.
27. J. P. Surivet, J. M. Vatele, Tetrahedron 1999, 55, 13011.
28. A. F. S. Barreto, O. E. Vercillo, C. K. Z. Andrade, M. A. Birkett, J. C. Caulfield, L. Wessjohann, Org. Bio. Chem. 2011, 9, 5024
29. I. A. Rivero, L. Guerrero, K. A. Espinoza, M. C. Meza, J. R. Rodriguez, Molecules 2009, 14, 1860
30. C. R. Strauss, D. W. Rooney, Green Chem. 2010, 12, 1340.
31. M. Jida, R. Poulain, S. Malaquin, P. Roussel, F. Niedercorn, B. Deprez, G. Laconde, Green Chem. 2010, 12, 961.
32. B. M. Choudary, M. L. Kantam, K. V. S. Ranganath, K. Mahendar, B. Sreedhar, J. Am. Chem. Soc. 2004, 126, 3396
33. E. Winter, L. D. Chiaradia, C. A. S. Cordova, R. J. Nunes, R. A. Yunes, T. B. Creczynski-Pasa, Bioorg. Med. Chem. 2010, 18, 8026
34. A. Basnet, P. Thapa, R. Karki, Y. Na, Y. Jahng, B. S. Jeong, T. C. Jeong, C. S. Lee, E. S. Lee, Bioorg. Med. Chem. 2007, 15, 4351
35. K. Aelvoet, A. S. Batsanov, A. J. Blatch, C. Grosjean, L. G. S. Patrick, C. A. Smethurst, A. Whiting, Angew. Chem., Int. Ed. 2008, 47, 768
36. A. R. Martin, K. Mohanan, L. Toupet, J. Vasseur, M. Smietana, Eur. J. Org. Chem. 2011, 3184
37. N. A. Begum, N. Roy, R. A. Laskar, K. Roy, Med. Chem. Res. 2011, 20, 184
38. J. V. Allen, S. Bergeron, M. J. Griffiths, S. Mukherjee, S. M. Roberts, N. M. Williamson, L. U. Wu, J. Chem. Soc., Perkin Trans. 1 1998, 3171
39. C. M. Santos, A. M. S. Silva, J. A. S. Cavaleiro, A. Levai, T. Patonay, Eur. J. Org. Chem. 2007, 2877
40. W. Li, W. Wu, J. Yang, X. Liang, J. Ye, Synthesis 2011, 7, 1085.