Assembly of isoquinolines via CuI-catalyzed coupling of beta-keto esters and 2-halobenzylamines

Bao Wang; Biao Lu; Yongwen Jiang; Yihua Zhang; Dawei Ma

doi:10.1021/ol800900a

Assembly of isoquinolines via CuI-catalyzed coupling of beta-keto esters and 2-halobenzylamines

Org Lett. 2008 Jul 3;10(13):2761-3. doi: 10.1021/ol800900a. Epub 2008 May 29.

Authors

Bao Wang¹, Biao Lu, Yongwen Jiang, Yihua Zhang, Dawei Ma

Affiliation

¹ Center of Drug Discovery, China Pharmaceutical University, Nanjing 210009, China.

PMID: 18507393
DOI: 10.1021/ol800900a

Abstract

CuI-catalyzed coupling of 2-halobenzylamines with beta-keto esters or 1,3-diketones in i-PrOH under the action of K(2)CO(3) produced 1,2-dihydroisoquinolines as the coupling/condensative cyclization products, which underwent smooth dehydrogenation under air atmosphere to afford substituted isoquinolines.

Publication types

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

MeSH terms

Benzylamines / chemistry*
Bromine Compounds / chemistry*
Catalysis
Copper / chemistry*
Esters / chemistry*
Halogenation
Iodides / chemistry*
Isoquinolines / chemistry*
Molecular Structure

Substances

Benzylamines
Bromine Compounds
Esters
Iodides
Isoquinolines
Copper
cuprous iodide