Redox-neutral indole annulation cascades

Michael C Haibach; Indubhusan Deb; Chandra Kanta De; Daniel Seidel

doi:10.1021/ja110713k

Redox-neutral indole annulation cascades

J Am Chem Soc. 2011 Feb 23;133(7):2100-3. doi: 10.1021/ja110713k. Epub 2011 Jan 31.

Authors

Michael C Haibach¹, Indubhusan Deb, Chandra Kanta De, Daniel Seidel

Affiliation

¹ Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854, United States.

PMID: 21280625
DOI: 10.1021/ja110713k

Abstract

Aminobenzaldehydes react with indoles in an unprecedented cascade reaction. This acid-catalyzed redox-neutral annulation proceeds via a condensation/1,5-hydride shift/ring-closure sequence. Polycyclic azepinoindoles and related compounds are obtained in a single step with good to excellent yields.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Acids / chemistry
Benzaldehydes / chemistry
Catalysis
Indoles / chemistry*
Molecular Structure
Oxidation-Reduction

Substances

Acids
Benzaldehydes
Indoles
2-aminobenzaldehyde