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

Flavie Peudru (1) , Jean-François Lohier (1) , Mihaela Gulea (1, 2) , Vincent Reboul (1)

1 LCMT - Laboratoire de chimie moléculaire et thioorganique
2 LIT - Laboratoire d'Innovation Thérapeutique

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.

Mots clés: Three-component reaction; 1; β-lactam-condensed 1; 4-thiazepine; 3-thiazine; Staudinger reaction

Domaines: Chimie organique

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, 2016, 191 (2), pp.220 - 229. ⟨10.1080/10426507.2015.1072191⟩. ⟨hal-01830249⟩