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A study of the reaction between 2,4‐disubstituted‐2,3‐dihydro‐1,5‐benzothiazepines and ketenes generated in situ from chloro and dichloroacetyl chlorides
Author(s) -
Xing QiYi,
Wang HongZhong,
Zhou Xin,
Jin Sheng,
Li YueMing,
Chan Albert S. C.
Publication year - 2001
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.5570380302
Subject(s) - chemistry , substituent , chloroacetyl chloride , amine gas treating , ring (chemistry) , medicinal chemistry , derivative (finance) , aryl , lactam , chloride , organic chemistry , economics , alkyl , financial economics
In the presence of triethyl amine, the reaction of 2,4‐disubstituted‐2,3‐dihydro‐1,5‐benzothiazepine with chloro and dichloroacetyl chlorides produced not only the expected β‐lactam derivative of the benzo‐thiazepine, but also the ring opening product. Different results were obtained when the substituent at 2‐position of the benxothiazepine varied from methyl to aryl, and the substituent on the chloroacetyl chloride varied from H to Cl, or when carrying out the reaction at different temperatures. The structures of the obtained products and the reaction mechanism are discussed.