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Reaction of biguanides and related compounds. XVI. Synthesis of s ‐triazinones and fused s ‐triazinones by carbonylation of biguanides and related compounds with diethyl azodicarboxylate
Author(s) -
Kihara Yoshito,
Kabashima Shigeru,
Yamasaki Tetsuo,
Ohkawara Tadashi,
Furukawa Mitsuru
Publication year - 1990
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.5570270510
Subject(s) - chemistry , diethyl azodicarboxylate , moiety , ring (chemistry) , amide , carbonylation , biguanide , orthoester , stereochemistry , organic chemistry , medicinal chemistry , catalysis , triphenylphosphine , medicine , metformin , carbon monoxide , diabetes mellitus , endocrinology
Biguanides and the related compounds, in which a moiety of biguanide is involved in the structure as a part of the ring, were allowed to react with diethyl azodicarboxylate to afford triazinones and fused heterocycles including a triazinone ring, respectively. The mechanism of the reaction was elucidated to proceed through the initial formation of the amide intermediate, followed by cyclization to triazinone ring systems with elimination of nitrogen.