Facile synthesis of bis(indolyl)methanes using catalytic amount of iodine at room temperature under solvent-free conditions

Tetrahedron

Volumn 60, Issue 9, 2004, Pages 2051-2055

  Ji, Shun Jun ^a   Wang, Shun Yi ^a   Zhang, Yong ^a   Loh, Teck Peng ^a,b  

^a SOOCHOW UNIVERSITY   (China)

^b NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

Aldehydes; Bis(indolyl)methanes; Indoles; Iodine; Solvent free

Indexed keywords

1H,1'H 3,3' (4 METHOXYPHENYLMETHANEDIYL)BISINDOLE; 1H,1'H 3,3' (4 NITROPHENYLMETHANEDIYL)BISINDOLE; 1H,1'H 3,3' PHENYLMETHANEDIYLBISINDOLE; 2 [BIS (1H INDOL 3 YL)METHYL] 4 CHLOROPHENOL; 3,3' BIS(INDOLYL) 4 METHYLPHENYLMETHANE; ALDEHYDE DERIVATIVE; BENZO[1,3]DIOXOL 5 YLDIINDOL 3 YLMETHANE; DIINDOL 3 YL[2]THIENYLMETHANE; INDOLE DERIVATIVE; METHANE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; DRUG SYNTHESIS; PRIORITY JOURNAL; QUANTUM YIELD; ROOM TEMPERATURE; SUBSTITUTION REACTION;

EID: 1042298780     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.12.060     Document Type: Article

References (31)

1. Sundberg R.J. The Chemistry of Indoles. 1996;Academic Press, New York. p 113.
2. Porter J.K., Bacon C.W., Robins J.D., Himmelsbach D.S., Higman H.C. J. Agric. Food Chem. 25:1977;88-93.
3. Osawa T., Namiki M. Tetrahedron Lett. 24:1983;4719-4722.
4. Fahy E., Potts B.C.M., Faulkner D.J., Smith K. J. Nat. Prod. 54:1991;564-569.
5. Bifulco G., Bruno I., Riccio R., Lavayre J., Bourdy G. J. Nat. Prod. 58:1995;1254-1260.
6. Bell R., Carmeli S., Sar N. J. Nat. Prod. 57:1994;1587-1590.
7. Garbe T.R., Kobayashi M., Shimizu N., Takesue N., Ozawa M., Yukawa H. J. Nat. Prod. 63:2000;596-598.
8. Ehrlich P. Medicin Woche. 1901;151.
9. Morgan L., Schunior R. J. Org. Chem. 27:1962;3696-3697.
10. Remers W. Chem. Heterocycl. Compd. 25:1972;1-6.
11. Roomi M., MacDonald S. Can. J. Chem. 48:1970;139-142.
12. Gregorovich B., Liang K., Clugston D., Mac-Donald S. Can. J. Chem. 46:1968;3291-3294.
13. Woland W., Venkiteswaren M., Richards C. J. Org. Chem. 26:1961;4241-4248.
14. Banerji J., Chatterjee A., Manna S., Pascard C., Prange T., Shoolery J. Heterocycles. 15:1981;325-336.
15. Chatterjee A., Manna S., Banerji J., Pascard C., Prange T., Shoolery J. J. Chem. Soc., Perkin Trans. 1. 1980;553-555.
16. Babu G., Sridhar N., Perumal P.T. Synth. Commun. 30:2000;1609-1614.
17. Maiti A.K., Bhattacharyya P. J. Chem. Res. (S). 1997;424-425.
18. Chen D., Yu L., Wang P.G. Tetrahedron Lett. 37:1996;4467-4470.
19. Nagarajan R., Perumal P.T. Tetrahedron. 58:2002;1229-1232.
20. Nagarajan R., Perumal P.T. Synth. Commun. 32:2002;105-110.
21. Bandgar B.P., Shaikh K.A. Tetrahedron Lett. 44:2003;1959-1961.
22. Kobayashi S., Araki M., Yasuda M. Tetrahedron Lett. 36:1995;5773-5776.
23. Yadav J.S., Subba Reddy B.V., Murthy C.V.S.R., Kumar G.M., Madan C. Synthesis. 5:2001;783-787.
24. Yadav J.S., Reddy B.V.S., Sabitha G., Reddy G.S.K.K. Synthesis. 2000;1532-1534.
25. Basu M.K., Samajdar M.K., Becker F.F., Banik B.K. Synlett. 2:2002;319-321.
26. Yadav J.S., Reddy B.V.S., Rao C., Sabitha V., Reddy M.J. Synthesis. 2:2003;247-250.
27. Toda F., Tanaka K. Chem. Rev. 100:2000;1025-1074.
28. Chandrasekhar S., Narsihmulu C., Sultana S.S., Saritha B., Prakash S.J. Synlett. 4:2003;505-506.
29. Krishna R., Velmurugan D., Babu G., Perumal P.T. Acta Crystallogr. Sect. C: Cryst. Struct. Commun. 55:1999;75-78.
30. 3; crystal system: triclinic; space group: P-1 (#2); unit cell: a=7.1255(9) Å, b=12.1249(5) Å, c=12.5865(5) Å, α=68.89(2)°, β=82.29(2)°, γ=84.44(2)°.
31. Sullivan O. Rothery. Chem. Ind. 1972;849.