The base‐promoted dehydration of rac.‐ trans ‐tetrahydro‐6‐hydroxy‐4‐[(2‐(dimethylamino)ethyl]‐7‐(4‐methoxyphenyl)‐1,4‐thiazepin‐5(2 H )‐one | Zendy

Mohacsi Erno | Zendy; O'Brien Jay P. | Zendy

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The base‐promoted dehydration of rac.‐ trans ‐tetrahydro‐6‐hydroxy‐4‐[(2‐(dimethylamino)ethyl]‐7‐(4‐methoxyphenyl)‐1,4‐thiazepin‐5(2 H )‐one

Author(s) -

Mohacsi Erno,

O'Brien Jay P.

Publication year - 1991

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.5570280845

Subject(s) - chemistry , alkylation , dehydration , dimethyl sulfoxide , base (topology) , amide , medicinal chemistry , stereochemistry , chloride , catalysis , organic chemistry , biochemistry , mathematical analysis , mathematics

The base‐catalyzed alkylation of rac.‐ trans ‐tetrahydro‐6‐hydroxy‐7‐(4‐methoxyphenyl)‐1,4‐thiazepin‐5(2 H )‐one ( 1 ) with dimethylaminoethyl chloride in dimethyl sulfoxide provided predominantly rac.‐ trans ‐tetrahydro‐6‐hydroxy‐4‐[(2‐dimethylamino)ethyl]‐7‐(4‐methoxyphenyl)‐1,4‐thiazepin‐5(2 H )‐one ( 2 ) and in addition, 2,3‐dihydro‐4‐[2‐(dimethylamino)‐ethyl]‐7‐(4‐methoxyphenyl)‐1,4‐thiazepin‐5(4 H )‐one ( 3 ). A plausible mechanism is postulated for the dehydration of the rac.‐ trans ‐amide 2 .

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