Synthesis of 2‐phenyl‐3,4‐dihydro‐2 H ‐ and ‐3,4,5,6‐tetrahydro‐2 H ‐1,6‐benzothiazocine derivatives | Zendy

Press Jeffery B. | Zendy; Eudy Nancy H. | Zendy

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Synthesis of 2‐phenyl‐3,4‐dihydro‐2 H ‐ and ‐3,4,5,6‐tetrahydro‐2 H ‐1,6‐benzothiazocine derivatives

Author(s) -

Press Jeffery B.,

Eudy Nancy H.

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.5570200632

Subject(s) - chemistry , amidine , aluminum hydride , acylation , lithium (medication) , alkylation , thioether , amine gas treating , lactam , medicinal chemistry , hydride , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , medicine , hydrogen , methoxide , endocrinology

The resynthesis of 2‐phenyl‐3,4‐dihydro‐2 H ‐benzothiazocin‐5(6 H )‐one (1) was investigated in order to prepare derivatives with potential CNS activity. Lactam 1 could be converted to amidine derivatives 6a‐e via the intermediacy of the thioether 5a. Reduction of 1 with lithium aluminum hydride gave amine 8a . Reductive alkylation of 8a gave 9a and 9b while acylation of 8a gave derivatives 10a‐d . No interesting biological properties were found for these compounds.

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