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

✍ Scribed by Jacek G. Sośnicki; Tadeusz S. Jagodziński; Jürgen Liebscher

Publisher
Journal of Heterocyclic Chemistry
Year
1997
Tongue
English
Weight
427 KB
Volume
34
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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.

📜 SIMILAR VOLUMES

Conjugate addition of nitrogen nucleophi
Conjugate addition of nitrogen nucleophiles to an α, β-unsaturated pyrrolidinone
✍ Philip W.H Chan; Ian F Cottrell; Mark G Moloney 📂 Article 📅 1997 🏛 Elsevier Science 🌐 French ⚖ 236 KB

The conjugate addition of nitrogen nucleophiles to ct,13-unsaturated lactam lb under very mild conditions occurs in good yield with high diastereoselectivity. Deprotection provides a simple access to 13-aminopyrrolidinones in excellent overall yield.

ChemInform Abstract: Conjugate Addition
ChemInform Abstract: Conjugate Addition of Nitrogen Nucleophiles to an α,β- Unsaturated Pyrrolidinone.
✍ P. W. H. CHAN; I. F. COTTRELL; M. G. MOLONEY 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 35 KB 👁 1 views

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