Premium
Synthetic and structural studies of some chloro‐substituted methyl 2,1‐benzisoxazole‐3‐carboxylates and related compounds
Author(s) -
Mccord Tommy J.,
Smith David R.,
Swan Janet K.,
Goebel Anna M.,
Thornton Donald E.,
Yakshe Criss C.,
Davis Alvie L.
Publication year - 1979
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.5570160631
Subject(s) - chemistry , thionyl chloride , sulfite , nucleophile , chloride , carboxylate , medicinal chemistry , organic chemistry , catalysis
Methyl 5‐chloro‐ and 5,7‐dichloro‐2,1‐benzisoxazole‐3‐carboxylates have been synthesized by treatment of o ‐nitromandelic and 5‐chloro‐2‐nitroamandelic methyl esters, respectively, with thionyl chloride under appropriate reaction conditions. The structural assignments of both heterocyclic products were based on elemental and spectral analyses, and their conversion to the corresponding 5‐chloro‐ and 5,7‐dichloro substituted 2,1‐benzisoxazole‐3‐carboxylic acids and isatins. Methyl α‐chloro‐ o ‐nitrophenylacetate and o ‐nitrophenylcarbomethoxymethinyl sulfite were also obtained from reactions of methyl o ‐nitromandelate and thionyl chloride. A possible reaction mechanism involving two consecutive nucleophilic substitutions of methyl o ‐nitromandelate with thionyl chloride was proposed to account for the formation of methyl 5‐chloro‐2,1‐benzisoxazole‐3‐carboxylate.