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Synthesis of dimethyl heterocyclic‐ o ‐dicarboxylates using dimethyl acetylenedicarboxylate
Author(s) -
Tominaga Yoshinori,
Ueda Kazuo
Publication year - 2005
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570420301
Subject(s) - dimethyl acetylenedicarboxylate , chemistry , cycloaddition , pyridazine , reagent , pyridine , ring (chemistry) , medicinal chemistry , organic chemistry , catalysis
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[3,4‐ b ]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.