Synthesis of dimethyl heterocyclic-o-dicarboxylates using dimethyl acetylenedicarboxylate

✍ Scribed by Yoshinori Tominaga; Kazuo Ueda

• Book ID: 102892010
• Publisher: Journal of Heterocyclic Chemistry
• Year: 2005
• Tongue: English
• Weight: 508 KB
• Volume: 42
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570420301

✦ Synopsis

Dimethyl acetylenedicarboxylate (DMAD) is a very important and useful reagent for the preparation of dimethyl heterocyclic-o-dicarboxylates, which are key intermediates in the synthesis of fused pyridazine derivatives. The synthesis of thiopyranes by the Diels-Alder reaction of dithiocarboxylate derivatives, synthesis of various cyclazines by [2 + 8] cycloaddition reactions, and synthesis of dimethyl pyrazolo[3,4b]pyridine-5,6-dicarboxylates and polycyclic heterocycles containing the 1,6-naphthyridine ring system by the reaction of o-aminonitrile compounds with DMAD are described here.