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Annulated 1,2,3‐triazoles. 3 . Synthesis of 1,2,3‐triazolo[4,5‐ b ][1,5]benzoxazepin‐10(9 H )‐ones and 10‐(4‐substituted‐1‐piperazinyl)‐1,2,3‐triazolo[4,5‐ b ][1,5]benzoxazepines
Author(s) -
Nielsen Flemming E.,
Pedersen Erik B.
Publication year - 1985
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.5570220645
Subject(s) - chemistry , ring (chemistry) , titanium tetrachloride , medicinal chemistry , condensation , triazole , stereochemistry , catalysis , organic chemistry , physics , thermodynamics
10‐(4‐Substituted‐1‐piperazinyl)‐1,2,3‐triazolo[4,5‐b][1,5]benzoxazepines 11 were prepared in a three‐step synthesis starting from easily available 5‐chloro‐1,2,3‐triazole‐4‐carbonyl chlorides 7 by titanium tetrachloride catalyzed condensation of N‐(substituted)piperazines with 1,2,3‐triazolo[4,5‐b][1,5]benzoxazepin‐10(9H)‐ones 10 formed by ring closure of the intermediate amides 9 . Although lactams 10 were obtained as the sole product of the cyclisation at 80°, the unexpected by‐products 13 and 14 were formed in addition to 10c at 150° from 9c . The 4‐methoxybenzyl group in 11j was easily removed by solvolyses in TFA. Compounds 11d‐f and 11i were tested for psychotropic activity.