Novel Bicyclic P,S-Heterocycles via Stereoselective hetero-Diels–Alder Reactions of Thiochalcones with 1-Phenyl-4H-phosphinin-4-one 1-Oxide-Reference-Cited by-同舟云学术

Novel Bicyclic P,S-Heterocycles via Stereoselective hetero-Diels–Alder Reactions of Thiochalcones with 1-Phenyl-4H-phosphinin-4-one 1-Oxide

Published:2024-04-28 Issue:9 Volume:29 Page:2036
ISSN:1420-3049
Container-title:Molecules
language:en
Short-container-title:Molecules

Author:

Mlostoń Grzegorz¹^ORCID,Urbaniak Katarzyna¹,Palusiak Marcin²^ORCID,Łastawiecka Elżbieta³^ORCID,Frynas Sławomir³,Pietrusiewicz Kazimierz Michał³^ORCID,Heimgartner Heinz⁴^ORCID

Affiliation:

1. Department of Organic and Applied Chemistry, Faculty of Chemistry, University of Lodz, Tamka 12, 91-403 Lodz, Poland

2. Department of Physical Chemistry, Faculty of Chemistry, University of Lodz, Pomorska 163/165, 90-236 Lodz, Poland

3. Department of Organic and Crystal Chemistry, Institute of Chemical Sciences, Faculty of Chemistry, Maria Curie-Skłodowska University, Gliniana 33, 20-614 Lublin, Poland

4. Department of Chemistry, University of Zurich, Winterthurerstrasse 190, CH-8057 Zurich, Switzerland

Abstract

Thiochalcones undergo cycloaddition reactions in THF solution at 60 °C with the synthetically unexplored 1-phenyl-4H-phosphinin-4-one 1-oxide in a highly regio- and stereoselective manner, yielding hitherto unknown bicyclic P,S-heterocycles containing fused thiopyran and phosphinine rings. The stereochemical structures of two of the obtained (4+2)-cycloadducts were unambiguously assigned by means of the X-ray single-crystal analysis. Based on these assignments, a concerted mechanism of the hetero-Diels–Alder reaction via the preferred endo approach of the heterodiene from the less hindered P=O side of the phosphininone molecule is postulated to explain the established rac-(4RS,8SR,9SR,10SR)-configured (4+2)-cycloadducts isolated as major products.

Funder

The University of Lodz

Publisher

MDPI AG

Link

https://www.mdpi.com/1420-3049/29/9/2036/pdf

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