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

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.

SUBMITTER: Samarakoon TB

PROVIDER: S-EPMC3271938 | biostudies-literature | 2011 Oct

REPOSITORIES: biostudies-literature

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

Samarakoon Thiwanka B TB Loh Joanna K JK Rolfe Alan A Le Lisa S LS Yoon Sun Young SY Lushington Gerald H GH Hanson Paul R PR

Organic letters 20110907 19

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 sulfo ...[more]

PMID: 21899284

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