A facile and efficient addition reaction of nitrogen-containing heterocyclic compounds with DMAD under neat conditions

✍ Scribed by Hassan Valizadeh; Ashkan Shomali; Hamid Gholipour

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2011
• Tongue: English
• Weight: 99 KB
• Volume: 48
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.763

✦ Synopsis

Abstract

A simple and efficient method was developed for the reaction of dimethyl acetylenedicarboxylate with benzothiazole, isoquinoline, quinoline, 3‐bromopyridine, pyridine, benzoxazole, benzimidazole, and 5,6‐dimethyl benzimidazole for the high‐yield synthesis of the related heterocyclic products (1, 2, 3, 4, 5, 6, 7, 8) in very short reaction time under neat procedure. The reaction of isoquinoline, 3‐bromopyridine, and pyridine afforded to diastereomeric mixtures of products 2, 4, and 5, respectively. However, only one isomer of products 1, 3, 6, 7, and 8 were identified from the reaction of benzothiazole, quinoline, benzoxazole, benzimidazole, and 5,6‐dimethyl benzimidazole, respectively. Benzotriazole afforded to product 9 under these conditions. For comparison, the reactions were examined in different reaction mediums and/or under microwave irradiation. J. Heterocyclic Chem., (2011).