A modular reaction pairing approach to the diversity-oriented synthesis of fused- and bridged-polycyclic sultams

Org Lett. 2011 Oct 7;13(19):5148-51. doi: 10.1021/ol201962n. Epub 2011 Sep 7.

Abstract

A reaction pairing strategy centered on utilization of a reaction triad (sulfonylation, S(N)Ar addition and Mitsunobu alkylation) generating skeletally diverse, tricyclic and bicyclic benzofused sultams is reported. Pairing sulfonylation and S(N)Ar reactions yields bridged, tricyclic and bicyclic benzofused sultams. Application of the Mitsunobu reaction in a sulfonylation-Mitsunobu-S(N)Ar pairing allows access to benzthiazocine-1,1-dioxides, while a simple change in the order of pairing to sulfonylation-S(N)Ar-Mitsunobu affords structurally different, bridged tricyclic benzofused sultams.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Heterocyclic Compounds / chemical synthesis*
  • Molecular Structure
  • Sulfonamides / chemical synthesis*

Substances

  • Heterocyclic Compounds
  • Sulfonamides