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Synthesis 2011(9): 1413-1418  
DOI: 10.1055/s-0030-1259971
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

One-Pot Regioselective Synthesis of 3-Benzylthiazolo[3,2-a]indoles by Sequential Sonogashira Coupling Followed by Triethylamine-Induced Cyclization

K. C. Majumdar*, Sanjay Nath
Department of Chemistry, University of Kalyani, Kalyani 741235, W. B., India
Fax: +91(33)25828282; e-Mail: kcm_ku@yahoo.co.in;
Further Information

Publication History

Received 31 January 2011
Publication Date:
24 March 2011 (online)

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Abstract

A number of 2-(prop-2-ynylthio)-1H-indoles have been utilized for the synthesis of 3-benzylthiazolo[3,2-a]indoles by Sonogashira­ acetylide-coupling followed by triethylamine-induced regioselective cyclization in a one-pot operation. The cyclization is dependent on the nature of the substituents on the phenyl ring of the substrates.

Key words

Sonogashira coupling - palladium catalyst - base-promoted­ cyclization - aryl iodide - thiazoloindole

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1

Present address: Tezpur University, Department of Chemistry, Assam-784 028, India.