Premium
Reaction of acetone oxime with dialkylmalonyl chlorides. Synthesis of 2‐(2‐propenyl)isoxazolidine‐3,5‐diones and 2,2‐ bis ‐(2‐(4,4‐dialkylisoxazolidine‐3,5‐dione))propanes
Author(s) -
Izydore Robert A.,
Davis Ronda G.,
Clements Nancy W.
Publication year - 1987
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.5570240605
Subject(s) - chemistry , propenyl , acetone , triethylamine , oxime , pyridine , organic chemistry , toluene , ethanol , medicinal chemistry
Reaction of acetone oxime with dialkylmalonyl chlorides in the presence of triethylamine gave as products 2‐(2‐propenyl)‐4,4‐dialkylisoxazolidine‐3,5‐diones 4 and 2,2‐ bis ‐(2‐(4,4‐dialkylisoxazolidine‐3,5‐dione))propanes 5 . The 4,4‐dialkylisoxazolidine‐3,5‐diones 6 and dimethylketoximyl 4,4‐dialkylmalonates 7 were formed as minor products. Compounds 4 are stable in refluxing ethanol and in aqueous solution. Compounds 5 are stable when heated in refluxing toluene in the presence of either pyridine or monochloroacetic acid.