One-pot synthesis of 2-substituted indoles from 2-aminobenzyl phosphonium salts. A formal total synthesis of arcyriacyanin A

George A Kraus; Haitao Guo

doi:10.1021/ol801034x

One-pot synthesis of 2-substituted indoles from 2-aminobenzyl phosphonium salts. A formal total synthesis of arcyriacyanin A

Org Lett. 2008 Jul 17;10(14):3061-3. doi: 10.1021/ol801034x. Epub 2008 Jun 24.

Authors

George A Kraus¹, Haitao Guo

Affiliation

¹ Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA. [email protected]

PMID: 18572918
DOI: 10.1021/ol801034x

Abstract

The reaction of (2-aminobenzyl) triphenylphosphonium bromide with aromatic aldehydes or alpha,beta-unsaturated aldehydes under microwave-assisted conditions constitutes a new synthesis of 2-substituted indoles in high yields (81-97%) in a one-pot reaction. The adduct from indole-4-carboxaldehyde was an advanced intermediate in the synthesis of arcyriacyanin A.

Publication types

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

MeSH terms

Benzyl Compounds / chemistry
Catalysis
Combinatorial Chemistry Techniques
Indoles / chemical synthesis*
Indoles / chemistry
Maleimides / chemical synthesis*
Maleimides / chemistry
Molecular Structure
Organophosphorus Compounds / chemistry*

Substances

Benzyl Compounds
Indoles
Maleimides
Organophosphorus Compounds
arcyriacyanin A