Skip to Main content Skip to Navigation
Journal articles

Synthesis of 1,3-thiazines by a three-component reaction and their transformations into β-lactam-condensed 1,3-thiazine and 1,4-thiazepine derivatives

Abstract : Variously substituted 1,3-thiazines have been prepared by a three-component reaction involving a thioamide, an aldehyde, and an alkene. Two diastereomeric thiazines were transformed by stereoselective Staudinger reaction into the corresponding chloro-β-lactam-condensed-1,3-thiazines, and one of them was rearranged in basic media to afford a highly substituted 1,4-thiazepine. Several of the obtained compounds (six 1,3-thiazines and one β-lactam-condensed-1,3-thiazine) were analyzed by X-ray crystallography, which enabled to assign their spatial arrangement and stereochemistry.
Document type :
Journal articles
Complete list of metadatas

https://hal-normandie-univ.archives-ouvertes.fr/hal-01830249
Contributor : Jocelyne Levillain <>
Submitted on : Wednesday, July 4, 2018 - 5:50:45 PM
Last modification on : Thursday, July 2, 2020 - 3:21:26 AM

Identifiers

Citation

Flavie Peudru, Jean-François Lohier, Mihaela Gulea, Vincent Reboul. Synthesis of 1,3-thiazines by a three-component reaction and their transformations into β-lactam-condensed 1,3-thiazine and 1,4-thiazepine derivatives. Phosphorus, Sulfur, and Silicon and the Related Elements, Taylor & Francis, 2016, 191 (2), pp.220 - 229. ⟨10.1080/10426507.2015.1072191⟩. ⟨hal-01830249⟩

Share

Metrics

Record views

71