Efficient Synthesis of Bis(indolyl)methanes Catalyzed by Lewis Acids in Ionic Liquids

Shun-Jun Ji; Min-Feng Zhou; Da-Gong Gu; Shun-Yi Wang; Teck-Peng Loh

doi:10.1055/s-2003-41464

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synlett 2003(13): 2077-2079
DOI: 10.1055/s-2003-41464

LETTER

Efficient Synthesis of Bis(indolyl)methanes Catalyzed by Lewis Acids in Ionic Liquids

Shun-Jun Ji*^a, Min-Feng Zhou^a, Da-Gong Gu^a, Shun-Yi Wang^a, Teck-Peng Loh*^a,b
^a College of Chemistry and Chemical Engineering of Suzhou University, Suzhou, China, 215006
^b Department of Chemistry, 3 Science Drive 3, National University of Singapore, Singapore 117543
Fax: +86(512)65224873; e-Mail: shunjun@suda.edu.cn; e-Mail: chmlohtp@nus.edu.sg;

Further Information

Publication History

Received 20 July 2003
Publication Date:
08 October 2003 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

Abstract

Efficient electrophilic substitution reactions of indoles with various aldehydes proceed smoothly in ionic liquids using Lewis acids, In(OTf)₃, YbCl₃, InCl₃, BiCl₃, and ZnCl₂, to afford the corresponding bis(indolyl)methanes in high yields.

Key words

ionic liquids - In(OTf)₃ - Lewis acids - indoles - bis(indolyl)methanes

References

1 Sundberg RJ. The Chemistry of Indoles Academic Press; New York: 1970.

Google Scholar
2a Porter JK. Bacon CW. Robins JD. Himmelsbach DS. Higman HC. J. Agric. Food Chem. 1977, 25: 88

Crossref PubMed Google Scholar
2b Osawa T. Namiki M. Tetrahedron Lett. 1983, 24: 4719

Crossref PubMed Google Scholar
2c Fahy E. Potts BCM. Faulkner DJ. Smith K. J. Nat. Prod. 1991, 54: 564

Crossref PubMed Google Scholar
2d Bifulco G. Bruno I. Riccio R. Lavayre J. Bourdy G. J. Nat. Prod. 1995, 58: 1254

Crossref PubMed Google Scholar
2e Bell R. Carmell S. Sar N. J. Nat. Prod. 1994, 57: 1587

Crossref PubMed Google Scholar
2f Garbe TR. Kobayashi M. Shimizu N. Takesue N. Ozawa M. Yukawa H. J. Nat. Prod. 2000, 63: 596

Crossref PubMed Google Scholar
3a Roomi M. MacDonald S. Can. J. Chem. 1970, 48: 139

Crossref Google Scholar
3b Gregorovich B. Liang K. Clugston D. MacDonald S. Can. J. Chem. 1968, 46: 3291

Crossref Google Scholar
4a Woland W. Venkiteswaren M. Richards C. J. Org. Chem. 1961, 26: 4241

Google Scholar
4b Banerji J. Chatterjee A. Manna S. Pascard C. Prange T. Shoolery J. Heterocycles 1981, 15: 325

Google Scholar
5a Chatterjee A. Manna S. Banerji J. Pascard C. Prange T. Shoolery J. J. Chem. Soc, Perkin Trans. 1 1980, 553

Crossref Google Scholar
5b Babu G. Sridhar N. Perumal PT. Synth. Commun. 2000, 30: 1609

Crossref Google Scholar
6 Kobayashi S. Araki M. Yasuda M. Tetrahedron Lett. 1995, 36: 5773

Crossref Google Scholar
7 Yadav JS. Subba Reddy BV. Murthy CVSR. Kumar GM. Madan C. Synthesis 2001, 783

Article in Thieme Connect Google Scholar
8 Nagarajan R. Perumal PT. Tetrahedron 2002, 58: 1229

Crossref Google Scholar
9 Bandgar BP. Shaikh KA. Tetrahedron Lett. 2003, 44: 1959

Crossref Google Scholar
10a Wasserschied P. Keim W. Angew. Chem., Int. Ed. 2000, 39: 3772

Crossref Google Scholar
10b Welton T. Chem. Rev. 1999, 99: 2071

Crossref Google Scholar
10c Seddon KR. J. Chem. Technol. Biotechnol. 1997, 68: 351

Crossref Google Scholar
11a Kamal A. Chouhan G. Tetrahedron Lett. 2003, 44: 3337

Article in Thieme Connect Google Scholar
11b Lee S.-g. Park JH. J. Mol. Catal. 2003, 194: 49

Article in Thieme Connect Google Scholar
11c Yadav JS. Reddy BVS. Gayathri KU. Prasad AR. Synthesis 2002, 2537

Article in Thieme Connect Google Scholar
11d Yadav JS. Reddy BVS. Reddy PN. Rao MS. Synthesis 2003, 1387

Article in Thieme Connect Google Scholar
12 Chen S.-L. Ji S.-J. Loh T.-P. Tetrahedron Lett. 2003, 44: 240

Google Scholar