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

Midhun Sai Krishna Adusumalli; Lakshmi Narayana Sharma Konidena; Hima Bindu Gandham; Krishnaiah Kumari; Krishna Reddy Valluru; Satya Kameswara Rao Nidasanametla; Venkateswara Rao Battula; Hari Krishna Namballa

doi:10.3762/bxiv.2021.26.v1

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

Midhun Sai Krishna Adusumalli ,
Lakshmi Narayana Sharma Konidena ,
Hima Bindu Gandham ,
Krishnaiah Kumari ,
Krishna Reddy Valluru ,
Satya Kameswara Rao Nidasanametla ,
Venkateswara Rao Battula and
Hari Krishna Namballa

Submitting author affiliation:

City University of New York, new york, United States

Beilstein Arch. 2021, 202126. https://doi.org/10.3762/bxiv.2021.26.v1

Published 22 Mar 2021

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Read the peer-reviewed version of this preprint: https://doi.org/10.3762/bjoc.17.186

SUBJECT AREAS

Show All Preprints Nanotechnology Organic chemistry Bioorganic chemistry / chemical biology Catalysis Chemical methods and reactions Flow and process chemistry Green and sustainable chemistry Materials chemistry Medicinal and pharmaceutical chemistry Nano- and molecular-scale electronics Nano-biomaterials and bioscience Nanomagnetics Nanomaterials, thin films and nanointerfaces Nanomedicine Nanometrology and nanomechanics Nano-optics Nanopatterning, self-assembly and nanofabrication Nanostructures for energy and sensing applications Natural products chemistry Organo main group chemistry Other nanotechnology (unclassified) Other organic chemistry (unclassified) Photochemistry and photovoltaics Physical organic chemistry Supramolecular chemistry

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 Me₃Al. The reaction proceeds via a domino nucleophilic addition with subsequent intramolecular cyclisation. This method provides wide variety of substituted 1-aminoisoquinolines with good functional group tolerance. Furthermore, the synthetic utility of this protocol was demonstrated in the successful synthesis of antitumor agent CWJ-a-5 in gram scale.

Keywords: 1-aminoisoquinolines CWJ-a-5 2-(2-oxo-2-phenylethyl)benzonitriles nucleophilic addition intramolecular cyclisation

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Adusumalli, M. S. K.; Konidena, L. N. S.; Gandham, H. B.; Kumari, K.; Valluru, K. R.; Nidasanametla, S. K. R.; Battula, V. R.; Namballa, H. K. Beilstein Arch. 2021, 202126. doi:10.3762/bxiv.2021.26.v1

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aromatic	the word “aromatic”
aromatic aldehyde	the word “aromatic” OR “aldehyde”
+aromatic +aldehyde	both words “aromatic” AND “aldehyde”
+aromatic -aldehyde	the word “aromatic” but NOT “aldehyde”
“aromatic aldehyde”	the exact phrase “aromatic aldehyde”
benz*	words which begin with “benz”, such as “benzene” or “benzyl”
benz*yl	words that begin with “benz” and end with “yl”, such as “benzyl” or “benzoyl”
benzyl~	words that are close to the word “benzyl”, such as “benzoyl” (i.e., fuzzy search)