Uncatalyzed addition of indoles and N-methylpyrrole to 3-formylchromones: synthesis of (chromon-3-yl)bis(indol-3-yl)methanes and E-2-hydroxy-3-(1-methylpyrrol-2-ylmethylene)chroman-4-ones under solvent-free conditions

Tetrahedron Letters

Volumn 48, Issue 42, 2007, Pages 7436-7439

  Sosnovskikh, Vyacheslav Ya ^a   Irgashev, Roman A ^a  

^a URAL FEDERAL UNIVERSITY   (Russian Federation)

Author keywords

(Chromon 3 yl)bis(indol 3 yl)methanes; 3 Formylchromones; Conjugate addition; E 2 Hydroxy 3 (1 methylpyrrol 2 ylmethylene)chroman 4 ones; Indoles; N Methylpyrrole

Indexed keywords

(CHROMON 3 YL)BIS(INDOL 3 YL)METHANE DERIVATIVE; 1 METHYLPYRROLE; 2 HYDROXY 3 (1 METHYLPYRROL 2 YLMETHYLENE)CHROMAN 4 ONE DERIVATIVE; 3 FORMYLCHROMONE DERIVATIVE; ALDEHYDE DERIVATIVE; CHROMAN DERIVATIVE; INDOLE DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; SYNTHESIS;

EID: 34548691864     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.08.078     Document Type: Article

References (29)

1. Ghosh C.K. J. Heterocycl. Chem. 20 (1983) 1437-1445
2. Sabitha G. Aldrichim. Acta 29 (1996) 15-25
3. Ghosh C.K. Heterocycles 63 (2004) 2875-2898
4. Gašparová R., and Lácová M. Molecules 10 (2005) 937-960
5. Reddy P.N., Reddy Y.T., Amaravathi M., Rao M.K., and Rajitha B. Heterocycl. Commun. 10 (2004) 301-304
6. Kumar V.N., Reddy Y.T., Narasimhareddy P., Rajitha B., and Clercq E.D. ARKIVOC 15 (2006) 181-188
7. Maiti A.K., and Bhattacharyya P. J. Chem. Res. (S) (1997) 424-425
8. Zeng X.-F., Ji S.-J., and Wang S.-Y. Tetrahedron 61 (2005) 10235-10241
9. Ko S., Lin C., Tu Z., Wang Y.-F., Wang C.-C., and Yao C.-F. Tetrahedron Lett. 47 (2006) 487-492
10. Xia M., Wang S., and Yuan W. Synth. Commun. 34 (2004) 3175-3182
11. Lin X.-F., Cui S.-L., and Wang Y.-G. Synth. Commun. 36 (2006) 3153-3160
12. Mo L.-P., Ma Z.-C., and Zhang Z.-H. Synth. Commun. 35 (2005) 1997-2004
13. Chen D., Yu L., and Wang P.G. Tetrahedron Lett. 37 (1996) 4467-4470
14. Chakrabarty M., Ghosh N., Basak R., and Harigaya Y. Tetrahedron Lett. 43 (2002) 4075-4078
15. Ji S.-J., Wang S.-Y., Zhang Y., and Loh T.-P. Tetrahedron 60 (2004) 2051-2055
16. Wang S.-Y., and Ji S.-J. Tetrahedron 62 (2006) 1527-1535
17. Sobral A.J.F.N., Rebanda N.G.C.L., da Silva M., Lampreia S.H., Silva M.R., Beja A.M., Paixão J.A., and Rocha Gonsalves A.M.dA. Tetrahedron Lett. 44 (2003) 3971-3973
18. Rohand T., Dolusic E., Ngo T.H., Maes W., and Dehaen W. ARKIVOC X (2007) 307-324
19. Kusurkar R.S., Nayak S.K., and Chavan N.L. Tetrahedron Lett. 47 (2006) 7323-7326
20. Chakrabarty M., Basak R., and Harigaya Y. Heterocycles 55 (2001) 2431-2447
21. Horton D.A., Bourne G.T., and Smythe M.L. Chem. Rev. 103 (2003) 893-930
22. Sosnovskikh V.Ya., and Irgashev R.A. Izv. Akad. Nauk, Ser. Khim. (2006) 2208-2209 (Russ. Chem. Bull., Int. Ed. 2006, 55, 2294-2295)
23. Sosnovskikh V.Ya., and Irgashev R.A. Lett. Org. Chem. 4 (2007) 344-351
24. 2: C, 79.98; H, 4.65; N, 7.17. Found: C, 79.66; H, 4.47; N, 6.99.
25. Sundberg R.D. Pyrroles and their Benzo Derivatives: Synthesis and Application. In: Katritzky A.R., and Rees C.W. (Eds). Comprehensive Heterocyclic Chemistry Pergamon Vol. 4 (1984), Oxford 313-376
26. 3: C, 70.58; H, 5.13; N, 5.49. Found: C, 70.38; H, 5.14; N, 5.41.
27. Basavaiah D., and Rao A.J. Tetrahedron Lett. 44 (2003) 4365-4368
28. Basavaiah D., Reddy R.J., and Rao J.S. Tetrahedron Lett. 47 (2006) 73-77
29. Luo S., Mi X., Xu H., Wang P.G., and Cheng J.-P. J. Org. Chem. 69 (2004) 8413-8422