"Synthesis of substituted 2-vinyl and 2-phenylbenzimidazoles and progre" by Jeremiah W. Hubbard

Semester

Fall

Date of Graduation

2008

Document Type

Dissertation

Degree Type

PhD

College

Eberly College of Arts and Sciences

Department

Chemistry

Committee Chair

Bjorn C G Soderberg

Abstract

Synthesis of 2-alkenyl and 2-arylbenzimidazoles, having a variety of functional groups, has been accomplished via a novel palladium-catalyzed reductive N-heteroannulation of 2-nitro- N-alkyl or N-benzyl benzenamines. The cyclization precursors are readily prepared from commercially available compounds by a variety of methods. In addition, the first total synthesis of ht-13-A has been studied. The key steps of the synthesis are a Mitsunobu reaction, an intramolecular Heck reaction, and a reductive N-heteroannulation.

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