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Synthesis of Tetrafunctionalized 2‐Azido‐3‐hydroxy‐1,4‐diones and Their Transformation into 5‐Substituted 3‐Acylisoxazoles
Author(s) -
JuhászTótha Éva,
Patonay Tamás
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200209)2002:17<3055::aid-ejoc3055>3.0.co;2-8
Subject(s) - chemistry , synthon , adduct , base (topology) , chloride , alkene , coupling reaction , medicinal chemistry , stereochemistry , organic chemistry , combinatorial chemistry , catalysis , mathematical analysis , mathematics
An efficient synthesis of 2‐azido‐3‐hydroxy‐1,4‐diones, based on the base‐induced coupling of α‐azido ketones and α‐oxo aldehydes, has been developed. The coupling reaction took place with moderate to good diastereoselectivity. The relative configurations of the adducts have been determined by X‐ray analysis. Treatment of tetrafunctionalized synthons 2‐azido‐3‐hydroxy‐1,4‐diones with mesyl chloride in the presence of base afforded 5‐substituted 3‐acylisoxazoles, through 2‐azido‐2‐alkene‐1,4‐dione intermediates. Analogous treatment of α‐azido ketones with α‐oxo esters resulted in the formation of the unstable 3‐azido‐2‐hydroxy‐4‐oxobutanoates. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)