Me3Al-mediated domino nucleophilic addition/intramolecular cyclisation of 2-(2-oxo-2-phenylethyl)benzonitriles with amines; a convenient approach for the synthesis of substituted 1-aminoisoquinolines

Authors

Krishna M. S. Adusumalli, Andhra University
Lakshmi N.S. Konidena, GVK Biosciences Private Limited
Hima B. Gandham, Andhra University
Krishnaiah Kumari, GVK Biosciences Private Limited
Krishan R. Valluru, GVK Biosciences Private Limited
Satya K.R. Nidasanametla, GVK Biosciences Private Limited
Venkateswara R. Battula, Andhra University
Hari K. Namballa, CUNY Hunter CollegeFollow

Document Type

Article

Publication Date

11-16-2021

Abstract

A simple and efficient protocol for the construction of 1-aminoisoquinolines was achieved by treating 2-(2-oxo-2- phenylethyl)benzonitriles with amines in the presence of Me 3 Al. The reaction proceeds via a domino nucleophilic addition with subsequent intramolecular cyclisation. This method provides a wide variety of substituted 1-aminoisoquinolines with good func- tional group tolerance. Furthermore, the synthetic utility of this protocol was demonstrated in the successful synthesis of the anti- tumor agent CWJ-a-5 in gram scale.

Comments

This work was originally published in Beilstein Journal of Organic Chemistry and can be found at https://doi.org/10.3762/bjoc.17.186.

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