DIASTEREOSELECTIVE MICHAEL ADDITION OF NITROGEN AND SULFUR-NUCLEOPHILES TO ALPHA,BETA-UNSATURATED DELTA-THIOLACTAMS

Authors
SOSNICKI JG JAGODZINSKI TS LIEBSCHER J
Citation
Jg. Sosnicki et al., DIASTEREOSELECTIVE MICHAEL ADDITION OF NITROGEN AND SULFUR-NUCLEOPHILES TO ALPHA,BETA-UNSATURATED DELTA-THIOLACTAMS, Journal of heterocyclic chemistry, 34(2), 1997, pp. 643-648
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of heterocyclic chemistry → ACNP
ISSN journal
0022152X
Volume
34
Issue
2
Year of publication
1997
Pages
643 - 648
Database
ISI
SICI code
0022-152X(1997)34:2<643:DMAONA>2.0.ZU;2-Z
Abstract
5,6-Dihydropyridine-2-thiones 2 are synthesized from 5,6-dihydropyridi n-2-ones 1 and Lawesson reagent. Stereoselective Michael-like addition of amines, methylhydrazine or functionalized thiols affords trans pip eridine-2-thiones 5 with the corresponding heterosubstituent in positi on 4 as major products. The configuration of the adducts 5 was determi ned by nmr-techniques.