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Synthesis and alkylation of 3,4‐dihydro‐1 H ‐1,3‐4‐benzotriazepine‐2,5‐diones and related systems
Author(s) -
Karp Gary M.
Publication year - 1996
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.5570330421
Subject(s) - chemistry , hydrazine (antidepressant) , alkylation , derivative (finance) , chloride , medicinal chemistry , thio , organic chemistry , catalysis , chromatography , financial economics , economics
A synthesis of the 1,3,4‐benzotriazepine‐2,5‐dione 2a and its 2‐thio analog 11 is described. The key step was the mild and efficient cyclization of the o ‐(aminobenzoyl)hydrazine 10 , obtained from the reaction of a protected hydrazine derivative with the o ‐nitrobenzoyl chloride 3 . Alkylation of 2a takes place exclusively at N ‐3 while alkylation of 11 takes place on sulfur. Cyclization of the o ‐(aminobenzoyl)hydrazine 14 gave the 2,4(1 H ,3 H )‐quinazolinedione 15 as the sole product.