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Reaction of 2‐dimethylaminomethylene‐1,3‐diones with dinucleophiles. II. Synthesis of 5‐(alkyl)(phenyl)‐4‐acylisoxazoles and 6,7‐dihydro‐1,2‐benzisoxazol‐4(5 H )‐ones
Author(s) -
Menozzi Giulia,
Sche Pietro,
Mosti Luisa
Publication year - 1983
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.5570200327
Subject(s) - chemistry , sodium methoxide , hydroxylamine hydrochloride , alkyl , methanol , medicinal chemistry , cyclohexane , hydroxylamine , hydrochloride , yield (engineering) , organic chemistry , materials science , metallurgy
The reaction of open‐chain and cyclohexane sym ‐2‐dimethylaminomethylene‐1,3‐diones with hydroxylamine hydrochloride in refluxing methanol gave in good to moderate yields a series of 5‐(alkyl)(phenyl)‐4‐acylisoxazoles and 6,7‐dihydro‐1,2‐benzisoxazol‐4(5 H )‐ones, respectively. As 3‐unsubstituted isoxazoles, all these compounds easily isomerized with sodium methoxide to the corresponding 2‐cyano‐1,3‐diones in high yields.