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Studies on 1,2,3‐triazoles. Part XI. A new entry to the benzopyrano[2,3‐ D ]‐1,2,3‐triazole system. Cyclization of 1‐benzyl‐5‐chloro‐4‐(2‐hydroxybenzoyl)‐1 H ‐1,2,3‐triazoles
Author(s) -
Buckle Derek R.
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.5570220120
Subject(s) - chemistry , resorcinol , acylation , benzene , yield (engineering) , friedel–crafts reaction , triazole , alkylation , base (topology) , medicinal chemistry , d 1 , organic chemistry , catalysis , mathematical analysis , materials science , mathematics , metallurgy , biochemistry , receptor
The acylation of simple arenes such as benzene and alkylated benzenes with N ‐protected 5‐chloro‐1 H ‐1,2,3‐triazole‐4‐carboxylic acid chlorides under Friedel‐Crafts conditions results in excellent yields of the corresponding ketones. Resorcinol dimethyl ethers undergo similar acylation reactions in somewhat lower yield with concomitant monodemethylation, and these derivatives undergo a facile base mediated cyclization to 9‐oxo‐3 H ,9 H ‐benzopyrano[2,3‐ d ]‐1,2,3‐triazoles.