Lewis acid catalyzed electrophilic substitution of indole with aldehydes and Schiff's bases under microwave solvent-free irradiation

Synthetic Communications

Volumn 34, Issue 17, 2004, Pages 3175-3182

  Xia, Min ^a   Wang, Si Hai ^a   Yuan, Wei Bo ^a  

^a ZHEJIANG SCI TECH UNIVERSITY   (China)

Author keywords

Bis(Indolyl)methanes; Lewis acid catalysis; Microwave

Indexed keywords

3,3 BIS(INDOLYL) 4 CHLOROPHENYLMETHANE; 3,3 BIS(INDOLYL) 4 HYDROPHENYLMETHANE; 3,3 BIS(INDOLYL) 4 METHOXYLPHENYLMETHANE; 3,3 BIS(INDOLYL) 4 METHYLPHENYLMETHANE; 3,3 BIS(INDOLYL)PHENYLMETHANE; ALDEHYDE; INDOLE; INDOLE DERIVATIVE; LEWIS ACID; SCHIFF BASE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; ELECTRON; MICROWAVE RADIATION; REACTION TIME; SUBSTITUTION REACTION; SYNTHESIS;

EID: 5344239616     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-200028611     Document Type: Article

References (25)

1. (a) Osawa, T.; Namiki, M. Structure elucidation of streptindole: a novel genotoxic metabolite isolated from intestinal bacteria. Tetrahedron Lett. 1983, 24, 4719-4722;
2. (b) Garbe, T.R.; Kobayashi, M.; Shimizu, N.; Takesue, N.; Ozawa, M.; Yukawa, H. Indolyl carboxylicacids by condensation of indoles with α-keto acids. J. Nat. Prod. 2000, 63, 596-598.
3. (a) Morgan, L.; Schunior, R. The chemistry of neuraminic acids: the Ehrlich reaction. J. Org. Chem. 1962, 27, 3696-3697;
4. (b) Dolphin, D. Pophyrinogens and porphodimethene: intermediates in the synthesis of meso-tetraphenylporphines from pyrroles and benzaldehydes. J. Heterocyclic Chem. 1970, 7, 275-283.
5. (a) Roomi, M.; MacDonald, S. Reductive C-alkylation II. Can. J. Chem. 1970, 48, 139-143;
6. (b) Gregorovich, B.; Liang, K.; Clugston, D.; MacDonald, S. Reductive C-alkylation. Can. J. Chem. 1968, 46, 3291-3300.
7. Babu, G.; Sridhar, N.; Perumal, P.T. A convenient method of synthesis of bis-indolylmethanes: indium trichloride catalyzed reactions of indole with aldehydes and Schiff's bases. Synth. Commun. 2000, 30, 1609-1614.
8. Kobayashi, S.; Araki, M.; Yasuda, M. One pot synthesis of β-amino esters from aldehydes using lanthanide triflate as a catalyst. Tetrahedron Lett. 1995, 36, 5773-5776.
9. Yadav, J.S.; Subba Reddy, B.V.; Murth, C.V.S.R.; Kumar,.G.M.; Madan, C. Lithium perchlorate catalyzed reaction of indoles: an expeditious synthesis of bis(indolyl)methanes. Synthesis 2001, 783-787.
10. Chen, D.; Yu, L.; Wang, P.G. Lewis acid-catalyzed reactions in protic media: lathanide-catalyzed reactions of indoles with aldehydes or ketones. Tetrahedron Lett. 1996, 37, 4467-4470.
11. Nagarajan, R.; Perumal, P.T. Electrophilic substitution of indoles catalyzed by triphenyl phophonium perchlorate: synthesis of 3-acetyl indoles abd bis-indolylmethane derivatives. Synth. Commun. 2002, 32, 105-109.
12. 3 catalyzed reactions: synthesis of 3-acetyl indoles, bis-indolylmethane and indolylquinoline derivatives. Tetrahedron 2002, 58, 1229-1232.
13. Maiti, A.K.; Bhattacharyya, P. Montmorillonite clay catalyzed synthesis of bis(indol-3-yl) methanes and 1,2-bis(indol-3-yl)ethanes. J. Chem. Res. (S) 1997, 424-425.
14. (a) Varma, R.S. Solvent-free organic synthesis. Green Chemistry 1999, 1, 43-55;
15. (b) Loupy, A.; Petit, A.; Hamelin, J.; Texier-Boullet, F.; Jacquault, P.; Mathe, D. New solvent-free organic synthesis using focused microwaves. Synthesis 1998, 1213-1234.
16. Xia, M. Microwave irradiation for the oxidative 1,3-dipolar cycloaddition of aldehyde phenylhydrazones and methyl acrylate by (diacetoxy)iodobenzene. J. Chem. Res. (S) 2003, 418-419.
17. (a) Chakrabarty, M.; Ghosh, N.; Basak, R.; Harigaya, Y. Dry reaction of indoles with carbonyl compounds on montmorillonite K10 clay: a mild, expedient synthesis of diindolylalkanes and vibrindole A. Tetrahedron Lett. 2002, 43, 4075-4078;
18. (b) Chakrabarty, M.; Basak, R.; Harigaya, Y. A sojourn in the synthesis and bioactivity of diindolylalkanes. Heterocycles 2001, 55, 2431-2447.
19. Babu, G.; Sridhar, N.; Perumal, P.T. A convenient method of synthesis of bis-indolylmethanes: indium trichloride catalyzed reactions of indole with aldehydes and Schiff's bases. Synth. Commun. 2000, 39, 1609-1614.
20. Snyder, H.R.; Matterson, D. The synthesis of the 2-amino-3-(3-indolyl)- butyric acids (β-metheyltryptophans). J. Am. Chem. Soc. 1959, 79, 2217-2221.
21. (a) Banerji, J.; Kumar, M.; Sarkar, S. Electrophilic substitution reactions of indoles: part V reaction of indole with benzalaniline. Indian J. Chem. Sect. B. 1983, 22B, 27-29;
22. (b) Banerji, J.; Kumar, M.; Sarkar, S. Electrophilic substitution reactions of indoles: part IX-reaction of indole with iminium systems. Indian J. Chem. Sect. B. 1986, 25B, 1204-1208.
23. Lu, J.; Ma, H. Iron(III)-catalyzed synthesis of dihydropyrimidinones: improved conditions for the Biginelli reaction. Synlett. 2000, 63-64.
24. Kappe, C.O.; Falson, S.F. Polyphosphate ester-mediated synthesis of dihydropyrimidinones: improved conditions for the Biginelli reaction. Synlett. 1998, 718-720.
25. Bandgar, B.P.; Shaikh, K.A. Molecular iodine-catalyzed efficient and highly rapid synthesis of bis(indolyl)methanes under mild conditions. Tetrahedron Lett. 2003, 44, 1959-1961.