An efficient and direct solvent-free synthesis of naphtho[1,2-b]furans, naphtho[2,1-b]furans, and furo[3,2-c]chromenes

Synlett

Volumn , Issue 15, 2009, Pages 2542-2544

  Adib, Mehdi ^a   Mahdavi, Mohammad ^a   Bagherzadeh, Sharareh ^a   Bijanzadeh, Hamid Reza ^b  

^a UNIVERSITY OF TEHRAN   (Iran)

^b TARBIAT MODARES UNIVERSITY   (Iran)

Author keywords

Cyclizations; Furo 3,2c chromenes; Heterocycles; Isocyanides; Naphtho 2,1 b urans; Naphtho l,2 b furans; Solvent free synthesis; Three component reactions

Indexed keywords

4 HYDROXYCOUMARIN; 7 METHOXY 2 NITRONAPHTHO[2,1 B]FURAN; CHROMENE DERIVATIVE; FURAN DERIVATIVE; FURO[3,2 C]CHROMENE DERIVATIVE; N ALKYL 3 ARYLFURO[3,2 C]CHROMENE DERIVATIVE; N ALKYL 3 ARYLNAPHTHO[1,2 B]FURAN 2 AMINE DERIVATIVE; N ALKYL 3 ARYLNAPHTHO[2,1 B]FURAN 2 AMINE DERIVATIVE; NAPHTHO[1,2 B]FURAN DERIVATIVE; NAPHTHO[2,1 B]FURAN DERIVATIVE; NAPHTHOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; HEATING; ONE POT SYNTHESIS;

EID: 72049123730     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1217736     Document Type: Article

References (31)

1. Abdul-Aziz, M.; Auping, J. V.; Meador, M. A. J. Org. Chem. 1995, 60, 1303.
2. Frederiksen, P. K.; Jorgensen, M.; Ogilby, P. R. J. Am. Chem. Soc. 2001, 123, 1215.
3. Sheats, J. R.; Anthoniadis, H.; Hueschen, M.; Leonard, W.; Miller, J.; Moon, R.; Roitman, D.; Stocking, A. Science 1996, 273, 884.
4. Hide, F.; Díaz-Garzía, M. A.; Schwartz, B. J.; Heeger, A. J. Acc. Chem. Res. 1997, 30, 430.
5. Albota, M.; Beljonne, D.; Brédas, J.-L.; Ehrlich, J. E.; Fu, J.-Y.; Heikal, A. A.; Hess, S. E.; Kogej, T.; Levin, M. D.; Marder, S. R.; McCord-Maughon, D.; Perry, J. W.; Rökel, H.; Rumi, M.; Subramaniam, G.; Webb, W. W.; Wu, X.-L.; Xu, C. Science 1998, 281, 1653.
6. (a) Bohlmann, F.; Zdero, C. Chem. Ber. 1977, 110, 487.
7. (b) Braga de Oliveira, A.; De Oliveira, G. G.; Carazza, F.; Braz Filho, R.; Moreira Bâcha, C.T.; Bauer, L.; Silva, G. A. de A. B.; Siqueira, N. C. S. Tetrahedron Lett. 1978, 30, 2653.
8. Qian, X.; Zhang, Y.; Ni, C. Hua. Lig. Dax. Xue. 1994, 20, 336;
9. Chem. Abstr. 1994, 121, 3718t.
10. Einhorn, J.; Demerseman, P.; Royer, R.; Cavier, R.; Gayral, P. Eur. J. Med. Chem. 1984, 405.
11. Giovanninetti, G.; Cavrini, V.; Chiarini, A.; Garuti, L.; Mannini-Palenzona, A. Farmaco, Ed. Sci. 1974, 29, 375.
12. Gaggi, R.; Giovanninetti, G.; Garuti, L. Farmaco, Ed. Sci. 1982, 37, 149.
13. (a) Hranjec, M.; Grdisa, M.; Pavelic, K.; Boykin, D. W.; Karminski-Zamola, G. Farmaco 2003, 58, 1319.
14. (b) Mahadevan, K. M.; Padmashali, B.; Vaidya, V. P. Indian J. Heterocycl. Chem. 2001, 11, 15.
15. Mahadevan, K. M.; Vaidya, V. P. Indian J. Pharm. Sci. 2003, 65, 128.
16. (a) Ronto, G.; Grof, P.; Buisson, J. P.; Einhorn, J.; Demerseman, P. Mutagenesis 1992, 7, 243.
17. (b) Debnath, A. K.; Hansch, C.; Kim, K. H.; Martin, Y. C. J. Med. Chem. 1993, 36, 1007.
18. Nair, V.; Menon, R. S.; Vinod, A. U.; Viji, S. Tetrahedron Lett. 2002, 43, 2293.
19. El Kaïm, L.; Grimaud, L.; Oble, J. Org. Biomol. Chem. 2006, 4, 3410.
20. (a) Solvent-Free Organic Synthesis; Tanaka, K., Ed.; WileyVCH; Weinheim, 2004.
21. (b) Tanaka, K.; Toda, F. Chem. Rev. 2000, 100, 1025.
22. (a) Adib, M.; Sayahi, M. H.; Ziyadi, H.; Zhu, L. G.; Bijanzadeh, H. R. Synthesis 2008, 3289.
23. (b) Adib, M.; Sheibani, E.; Zhu, L. G.; Bijanzadeh, H. R. Synlett 2008, 2941.
24. Adib, M.; Mohammadi, B.; Bijanzadeh, H. R. Synlett 2008, 3180.
25. Adib, M.; Mohammadi, B.; Bijanzadeh, H. R. Synlett 2008, 177.
26. (e) Adib, M.; Sayahi, M. H.; Ziyadi, H.; Bijanzadeh, H. R.; Zhu, L. G. Tetrahedron 2007, 63, 11135.
27. (f) Adib, M.; Aali Koloogani, S.; Abbasi, A.; Bijanzadeh, H. R. Synthesis 2007, 3056.
28. (g) Adib, M.; Sheibani, E.; Abbasi, A.; Bijanzadeh, H. R. Tetrahedron Lett. 2007, 48, 1179.
29. (h) Adib, M.; Sheibani, E.; Mostofi, M.; Ghanbary, K.; Bijanzadeh, H. R. Tetrahedron 2006, 62, 3435.
30. Adib, M.; Mahdavi, M.; Mahmoodi, N.; Pirelahi, H.; Bijanzadeh, H. R. Synlett 2006, 1765.
31. 3 (347.41): C, 76.06; H, 6.09; N, 4.03. Found: C, 76.1; H, 6.1; N, 4.0.