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Syntheses for 2‐amino and 2‐mercapto‐2 H ‐1,4‐benzoxazin‐3(4 H )‐one and 2 H ‐1,4‐benzothiazin‐3(4 H )‐one as aza and thio analogues of the natural product blepharigenin
Author(s) -
Kluge Michael,
Sicker Dieter
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.5570330613
Subject(s) - chemistry , thio , hydroxamic acid , stereochemistry , natural product , medicinal chemistry
2‐Amino‐2 H ‐1,4‐benzoxazin‐3(4 H )‐one 3 , 2‐amino‐2 H ‐1,4‐benzothiazin‐3(4 H )‐one 4 , 2‐mercapto‐2 H ‐1,4‐benzoxazin‐3(4 H )‐one 7 , and 2‐mercapto‐2 H ‐1,4‐benzothiazin‐3(4 H )‐one 8 representing aza and thio analogues of the natural product's aglucone Blepharigenin (2‐hydroxy‐2 H ‐1,4‐benzoxazin‐3(4 H )‐one) from Gramineae and Acantnaceae species have been synthesized for the first time from their 2‐bromo precursors 1 and 2 . Attempts to similarly prepare the 4‐hydroxy derivatives of 7 and 8 , which would represent new thio analogues of the naturally occurring cyclic hydroxamic acid, 2,4‐dihydroxy‐2 H ‐1,4‐benzoxazin‐3(4 H )‐one, have failed.