Redox isomerization via azomethine ylide intermediates: N-alkyl indoles from indolines and aldehydes

Indubhusan Deb; Deepankar Das; Daniel Seidel

doi:10.1021/ol1031359

Redox isomerization via azomethine ylide intermediates: N-alkyl indoles from indolines and aldehydes

Org Lett. 2011 Feb 18;13(4):812-5. doi: 10.1021/ol1031359. Epub 2011 Jan 19.

Authors

Indubhusan Deb¹, Deepankar Das, Daniel Seidel

Affiliation

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

PMID: 21247142
DOI: 10.1021/ol1031359

Abstract

Indolines react with aromatic and heteroaromatic aldehydes to yield N-alkyl indoles in a benzoic acid catalyzed redox isomerization reaction. Azomethine ylides are intermediates in this process which was established by intramolecular [3 + 2] trapping experiments.

Publication types

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

MeSH terms

Aldehydes / chemistry*
Azo Compounds / chemistry
Benzoic Acid / chemistry
Catalysis
Indoles / chemical synthesis*
Indoles / chemistry
Molecular Structure
Oxidation-Reduction
Stereoisomerism
Thiosemicarbazones / chemistry

Substances

Aldehydes
Azo Compounds
Indoles
Thiosemicarbazones
azomethine
indoline
Benzoic Acid