Synthesis and alkylation of 3,4‐dihydro‐1 H ‐1,3‐4‐benzotriazepine‐2,5‐diones and related systems | Zendy

Karp Gary M. | Zendy

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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.

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