Synthesis of a Library of 1,5,2-Dithiazapine 1,1-Dioxides. Part 2: Routes to Bicyclic Sultams

Abstract

The synthesis of a library of bicyclic sultams incorporating the 1,5,2-dithiazepine 1,1-dioxide moiety is reported. Following scaffold synthesis via a one-pot sulfonylation/intramolecular thia-Michael protocol, several additional cyclization strategies have been realized enabling access to new bicyclic sultams.

A summary of seven- and eight-membered ring sultam syntheses via three Michael addition reactions

“…We provide a short summary of this methodology to introduce the reader to several of these highyielding routes in one place. Similar synthetic paths were reported previously by us and the Hanson group [36][37][38][39][40][41][42][43][44][45]. In this work we combine all our synthetic methods for sevenand eight-membered ring -N,N-, -N,O-, and -N,S-sultams to give readers a more complete picture of the use of vinyl sulfonamides as starting materials to generate sultams.…”