Diastereoselective michael addition of nitrogen and sulfur‐nucleophiles to α,β‐unsaturated δ‐thiolactams | Zendy

Sośnicki Jacek G. | Zendy; Jagodziński Tadeusz S. | Zendy; Liebscher Jürgen | Zendy

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Diastereoselective michael addition of nitrogen and sulfur‐nucleophiles to α,β‐unsaturated δ‐thiolactams

Author(s) -

Sośnicki Jacek G.,

Jagodziński Tadeusz S.,

Liebscher Jürgen

Publication year - 1997

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.5570340249

Subject(s) - chemistry , michael reaction , reagent , nucleophile , adduct , piperidine , stereoselectivity , organic chemistry , methylhydrazine , sulfur , medicinal chemistry , phenylhydrazine , catalysis

5,6‐Dihydropyridine‐2‐thiones 2 are synthesized from 5,6‐dihydropyridin‐2‐ones 1 and Lawesson reagent. Stereoselective Michael‐like addition of amines, methylhydrazine or functionalized thiols affords trans piperidine‐2‐thiones 5 with the corresponding heterosubstituent in position 4 as major products. The configuration of the adducts 5 was determined by nmr‐techniques.

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