Microwave-Accelerated Solvent- and Catalyst-Free Synthesis of 4-Aminoaryl/alkyl-7-chloroquinolines and 2-Aminoaryl/alkylbenzothiazoles

Hashim F. Motiwala; Raj Kumar; Asit K. Chakraborti

doi:10.1071/CH06391

RESEARCH ARTICLE

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Microwave-Accelerated Solvent- and Catalyst-Free Synthesis of 4-Aminoaryl/alkyl-7-chloroquinolines and 2-Aminoaryl/alkylbenzothiazoles

Hashim F. Motiwala ^A , Raj Kumar ^A and Asit K. Chakraborti ^A ^B

+ Author Affiliations

- Author Affiliations

^A Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Sector 67, S.A.S. Nagar, Punjab 160 062, India.

^B Corresponding author. Email: akchakraborti@niper.ac.in

Australian Journal of Chemistry 60(5) 369-374 https://doi.org/10.1071/CH06391
Submitted: 23 October 2006 Accepted: 15 March 2007 Published: 28 May 2007

Abstract

An efficient synthesis of 4-aminoaryl/alkyl-7-chloroquinolines and 2-aminoaryl/alkylbenzothiazoles has been developed by microwave-accelerated regioselective aromatic nucleophilic substitution of 4,7-dichloroquinoline and 2-chlorobenzothiazole with aromatic and aliphatic amines under solvent-free conditions in the absence of any added protic or Lewis acid catalyst. Chemoselective reaction with the amino group in preference to the phenolic hydroxy group was observed. Thus, the treatment of 4,7-dichloroquinoline (1 equiv.) with a mixture of aniline (2 equiv.) and phenol (2 equiv.) afforded exclusive formation of 4-aminophenyl-7-chloroquinoline. When 4,7-dichloroquinoline (1 equiv.) was separately treated with 2-aminophenol (2 equiv.) and 4-aminophenol (2 equiv.), 4-(2′-hydroxyphenyl)-7-chloroquinoline and 4-(4′-hydroxyphenyl)-7-chloroquinoline, respectively, were formed.

References

Microwave-Accelerated Solvent- and Catalyst-Free Synthesis of 4-Aminoaryl/alkyl-7-chloroquinolines and 2-Aminoaryl/alkylbenzothiazoles

Abstract

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