A Direct and an Efficient Regioselective Synthesis of 1,2-Benzothiazine 1,1-dioxides, β-Carbolinones, Indolo[2,3- c]pyran-1-ones, Indolo[3,2- c]pyran-1-ones, Thieno[2,3- c]pyran-7-ones and Pyrano[3',4':4,5]imidazo[1,2- a]pyridin-1-ones via Tandem Stille/Heterocyclization Reaction

Badr Jismy; Khalil Cherry; Carine Maaliki; Samuel Inack Ngi; Mohamed Abarbri

doi:10.3390/molecules25215137

A Direct and an Efficient Regioselective Synthesis of 1,2-Benzothiazine 1,1-dioxides, β-Carbolinones, Indolo[2,3- c]pyran-1-ones, Indolo[3,2- c]pyran-1-ones, Thieno[2,3- c]pyran-7-ones and Pyrano[3',4':4,5]imidazo[1,2- a]pyridin-1-ones via Tandem Stille/Heterocyclization Reaction

Molecules. 2020 Nov 4;25(21):5137. doi: 10.3390/molecules25215137.

Authors

Badr Jismy¹, Khalil Cherry², Carine Maaliki¹, Samuel Inack Ngi³, Mohamed Abarbri¹

Affiliations

¹ Laboratoire de Physico-Chimie des Matériaux et des Electrolytes Pour l'Energie (PCM2E), EA 6299, Avenue Monge, Faculté des Sciences, Université de Tours, Parc de Grandmont, 37200 Tours, France.
² Laboratoire Matériaux, Catalyse, Environnement et Méthodes Analytiques (MCEMA), Campus Universitaire de Hadat, Université Libanaise, Beyrouth, Lebanon.
³ IKAMBA Organics, rue Edouard Branly, 37230 Fondettes, France.

Abstract

A general regioselective one-pot synthesis of 1,2-benzothiazine 1,1-dioxides from 2-iodo benzenesulfonamide moieties and allenylstannanes is described using a domino Stille-like/Azacyclization reaction. The conditions developed also opened a novel access to β-carbolinones, indolopyranones, thienopyranones and pyrano-imidazopyridines.

Keywords: 1,2-benzothiazine 1,1-dioxides; Stille/Heterocyclization reaction; indolo[2,3-c] and [3,2-c]pyrane-1-one derivatives; regioselective synthesis; β-carbolinones.

MeSH terms

Catalysis
Thiazines / chemical synthesis*
Thiazines / chemistry*

Substances

Thiazines