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Short Paper | Regular issue | Vol 87, No. 2, 2013, pp.389-397
Published online, 6th December, 2012
DOI: 10.3987/COM-12-12620
Synthesis of 3,4-Dihydroisoquinolines by Cyclization of 1-Bromo-2-(2-isocyanoalkyl)benzenes with Butyllithium

Kazuhiro Kobayashi,* Naoki Matsumoto, and Kota Matsumoto

*Division of Applied Chemistry, Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan

Abstract

A new and convenient method for the preparation of 3,3-disubstituted 3,4-dihydroisoquinolines has been developed. Thus, the reaction of 1-bromo-2-(bromomethyl)benzenes with (1-isocyano-1-lithioalkyl)benzenes, generated by the treatment of (1-isocyanoalkyl)benzenes with butyllithium, in THF at –78 ˚C gave the corresponding 1-(2-aryl-2-isocyanoalkyl)-2-bromobenzenes, which in turn were transformed into the desired products on treatment with butyllithium in THF at –78 ˚C.