Microwave-assisted one-pot synthesis of isoquinolines, furopyridines, and thienopyridines by palladium-catalyzed sequential coupling-imination-annulation of 2-bromoarylaldehydes with terminal acetylenes and ammonium acetate

Dingqiao Yang; Satvika Burugupalli; David Daniel; Yu Chen

doi:10.1021/jo300494a

Microwave-assisted one-pot synthesis of isoquinolines, furopyridines, and thienopyridines by palladium-catalyzed sequential coupling-imination-annulation of 2-bromoarylaldehydes with terminal acetylenes and ammonium acetate

J Org Chem. 2012 May 4;77(9):4466-72. doi: 10.1021/jo300494a. Epub 2012 Apr 17.

Authors

Dingqiao Yang¹, Satvika Burugupalli, David Daniel, Yu Chen

Affiliation

¹ Department of Chemistry and Biochemistry, Queens College and the Graduate Center of the City University of New York, Flushing, New York 11367, USA.

PMID: 22494334
DOI: 10.1021/jo300494a

Abstract

A palladium-catalyzed microwave-assisted one-pot reaction for the synthesis of isoquinolines is developed. The reaction is carried out by sequential coupling-imination-annulation reactions of ortho-bromoarylaldehydes and terminal alkynes with ammonium acetate, and a variety of substituted isoquinolines, furopyridines, and thienopyridines is prepared in moderate to excellent yields (up to 86%).

Publication types

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

MeSH terms

Acetates / chemistry*
Acetylene / chemistry*
Aldehydes / chemistry*
Alkynes / chemistry*
Isoquinolines / chemical synthesis*
Isoquinolines / chemistry*
Microwaves
Molecular Structure
Palladium / chemistry*
Thienopyridines / chemical synthesis*
Thienopyridines / chemistry*

Substances

Acetates
Aldehydes
Alkynes
Isoquinolines
Thienopyridines
Palladium
Acetylene
ammonium acetate