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Synthesis 2009(7): 1131-1136  
DOI: 10.1055/s-0028-1088004
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Three-Component Coupling of Isoquinoline, Activated Alkyne and Nitromethane: A Facile Synthesis of Nitromethyl Derivatives of 1,2-Dihydroisoquinolines

Jhillu S. Yadav*, Basi V. Subba Reddy, Nagendra Nath Yadav, Manoj K. Gupta
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500007, India
Fax: +91(40)27160512; e-Mail: yadav@iict.res.in;
Further Information

Publication History

Received 10 November 2008
Publication Date:
06 March 2009 (online)

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Abstract

A three-component coupling (3CC) of isoquinoline, activated alkynes and nitromethane has been achieved for the first time to produce nitromethyl derivatives of dihydroisoquinoline in excellent yields with high selectivity. The reaction proceeds smoothly at 25 ˚C without catalyst.

Key words

aza-Henry reaction - isoquinoline/quinoline - activated alkynes - nitromethane

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