Synthesis of N-functionalized/NH-multisubstituted indoles, thienopyrroles, pyrroloindoles, and pyrazolopyrroles via sequential one-pot base-mediated and copper-catalyzed inter- and intramolecular amination of 2-[2-bromo(het)aryl]-3-(het)aryl-3-(methylthio)acrylonitriles

S Vijay Kumar; B Saraiah; G Parameshwarappa; H Ila; Girijesh K Verma

doi:10.1021/jo501114a

Synthesis of N-functionalized/NH-multisubstituted indoles, thienopyrroles, pyrroloindoles, and pyrazolopyrroles via sequential one-pot base-mediated and copper-catalyzed inter- and intramolecular amination of 2-[2-bromo(het)aryl]-3-(het)aryl-3-(methylthio)acrylonitriles

J Org Chem. 2014 Sep 5;79(17):7961-78. doi: 10.1021/jo501114a. Epub 2014 Aug 7.

Authors

S Vijay Kumar¹, B Saraiah, G Parameshwarappa, H Ila, Girijesh K Verma

Affiliation

¹ New Chemistry Unit, Jawaharlal Nehru Centre for Advanced Scientific Research , Jakkur, Bangalore 560064, India.

PMID: 25072886
DOI: 10.1021/jo501114a

Abstract

A novel, efficient route to substituted 1-N-(het)aryl/NH-2-(het)aryl-3-cyanoindoles and related pyrrolo-fused heterocycles such as thienopyrroles, pyrroloindoles, and pyrazolopyrroles has been reported. The overall protocol involves sequential cycloamination of readily available 2-[2-bromo(het)aryl]-3-(het)aryl-3-(methylthio)acrylonitrile precursors with primary amines or amides via two key C-N bond-forming processes, one base-mediated intermolecular and the other Cu-catalyzed intramolecular arylamination leading to N(1)-C(2) and N(1)-C(7a) bond formation, respectively, in a two-step one-pot procedure.

Publication types

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

MeSH terms

Acrylonitrile / analogs & derivatives
Acrylonitrile / chemical synthesis*
Acrylonitrile / chemistry
Amination
Catalysis
Copper / chemistry*
Indoles / chemical synthesis*
Indoles / chemistry
Molecular Structure
Pyrroles / chemical synthesis*
Pyrroles / chemistry

Substances

Indoles
Pyrroles
thienopyrrole
Copper
Acrylonitrile