Cu(OTf)2 catalyzed synthesis of bis(5-methyl-2-furyl)methanes by condensation of 2-methylfuran with carbonyl compounds under solvent free conditions

Chinese Journal of Chemistry

Volumn 29, Issue 7, 2011, Pages 1483-1488

  Muthyala, Manoj Kumar ^a   Rao, V Kameswara ^a   Kumar, Anil ^a  

^a BIRLA INSTITUTE OF TECHNOLOGY AND SCIENCE   (India)

Author keywords

2 methylfuran; bis(5 methyl 2 furyl)methane; copper(II) triflate; Lewis acid; multicomponent condensation; solvent free condition

Indexed keywords

EID: 79960931718     PISSN: 1001604X     EISSN: 16147065     Source Type: Journal    
DOI: 10.1002/cjoc.201180269     Document Type: Article

References (37)

1. Butin, A. V.,;, Stroganova, T. A.,;, Kul'nevich, V. G.,. Chem. Heterocycl. Compd., 1999, 35, 757.
2. Butin, A. V.,;, Gutnov, A. V.,;, Abaev, V. T.,;, Krapivin, G. D.,. Molecules, 1999, 4, 52.
3. Pajewski, R.,;, Ostaszewski, R.,;, Ziach, K.,;, Kulesza, A.,;, Jurczak, J.,. Synthesis, 2004, 865.
4. Hall, J. E.,. US 4429090, 1984.
5. Gandini, A., EP 0379250, 1990.
6. Musau, R. M.,;, Whiting, A.,. J. Chem. Soc., Perkin Trans. 1, 1994, 2881.
7. He, Y.,;, Chen, Z.,;, Wu, C.,. Chin. J. Synth. Chem., 1993, 1, 123.
8. Stoll, M.,;, Winter, M.,;, Gautschi, F.,;, Flament, I.,;, Willhalm, B.,. Helv. Chim. Acta, 1967, 50, 628.
9. Shulezhko, A. A.,;, Rozhdestvenskaya, I. T.,;, Kiprianov, A. I.,. Zh. Org. Khim., 1970, 6, 2118.
10. Fukuda, M.,;, Fukunishi, A.,;, Mori, M., JP 06171214, 1994.
11. Nakanishi, M.,;, Mukai, T.,;, Inamasu, S., JP 44027990, 1969.
12. Brown, W. H.,;, French, W. N.,. Can. J. Chem., 1958, 36, 537.
13. Brown, W. H.,;, Hutchinson, B. J.,. Can. J. Chem., 1978, 56, 617.
14. Riad, A.,;, Mouloungui, Z.,;, Delmas, M.,;, Gaset, A.,. Synth. Commun., 1989, 19, 3169.
15. VanRhijn, W. M.,;, DeVos, D. E.,;, Sels, B. F.,;, Bossaert, W. D.,;, Jacobs, P. A.,. Chem. Commun., 1998, 317.
16. Li, T.,;, Cheng, S. I.,;, Lee, J.-F.,;, Jang, L.-Y.,. J. Mol. Catal. A: Chem., 2003, 198, 139.
17. Hashmi, A. S. K.,;, Schwarz, L.,;, Rubenbauer, P.,;, Blanco, M. C.,. Adv. Synth. Catal., 2006, 348, 705.
18. Nair, V.,;, Abhilash, K. G.,;, Vidya, N.,. Org. Lett., 2005, 7, 5857.
19. Algarraa, F.,;, Corma, A.,;, Garciaa, H.,;, Primoa, J.,. Appl. Catal. A: Gen., 1995, 128, 119.
20. Wewerka, E. M.,;, Loughran, E. D.,;, Walters, K. L.,. J. Appl. Polym. Sci., 1971, 15, 1437.
21. Stroganova, T. A.,;, Butin, A. V.,;, Sorotskaya, L. N.,;, Kul'nevich, V. G.,. ARKIVOC, 2000, 641.
22. Genovese, S.,;, Epifano, F.,;, Pelucchini, C.,;, Curini, M.,. Eur. J. Org. Chem., 2009, 1132.
23. Tanaka, K.,;, Toda, F.,. Chem. Rev., 2000, 100, 1025.
24. Cave, G. W. V.,;, Raston, C. L.,;, Scott, J. L.,. Chem. Commun., 2001, 2159.
25. Rothenberg, G.,;, Downie, A. P.,;, Raston, C. L.,;, Scott, J. L.,. J. Am. Chem. Soc., 2001, 123, 8701.
26. Kumar, R.,;, Selvam, C.,;, Kaur, G.,;, Chakraborti, A. K.,. Synlett, 2005, 1401.
27. Chakraborti, A. K.,;, Gulhane, R.,. Synlett, 2004, 627.
28. Ranu, B. C.,;, Banerjee, S.,;, Das, A.,. Tetrahedron Lett., 2006, 47, 881.
29. Ranu, B. C.,;, Banerjee, S.,. J. Org. Chem., 2005, 70, 4517.
30. Liang, X.,;, Gao, S.,;, Yang, J.,;, He, M.,. Catal. Commun., 2008, 10, 156.
31. Kumar, A.,;, Rao, V. K.,;, Rao, M. S.,. J. Heterocycl. Chem., 2010, in press.
32. Kumar, A.,;, Ahmad, I.,;, Rao, M. S.,. J. Sulf. Chem., 2010, 30, 570.
33. Rao, M. S.,;, Ahmad, I.,;, Khungar, B.,;, Kumar, A.,. Can. J. Chem., 2009, 87, 714.
34. Kumar, A.,;, Rao, M. S.,;, Ahmad, I.,;, Khungar, B.,. Aust. J. Chem., 2009, 62, 322.
35. Kumar, A.,;, Ahmad, I.,;, Rao, M. S.,. Can. J. Chem., 2008, 86, 899.
36. Kumar, A.,;, Jain, N.,;, Rana, S.,;, Chauhan, S. M. S.,. Synlett, 2004, 2785.
37. Ackman, R. G.,;, Brown, W. H.,;, Wright, G. F.,. J. Org. Chem., 1955, 20, 1147.