Me(3)Al-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

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...

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Autores principales: Adusumalli, Krishna M S, Konidena, Lakshmi N S, Gandham, Hima B, Kumari, Krishnaiah, Valluru, Krishna R, Nidasanametla, Satya K R, Battula, Venkateswara R, Namballa, Hari K
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2021
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8609244/
https://www.ncbi.nlm.nih.gov/pubmed/34876930
http://dx.doi.org/10.3762/bjoc.17.186
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author Adusumalli, Krishna M S
Konidena, Lakshmi N S
Gandham, Hima B
Kumari, Krishnaiah
Valluru, Krishna R
Nidasanametla, Satya K R
Battula, Venkateswara R
Namballa, Hari K
author_facet Adusumalli, Krishna M S
Konidena, Lakshmi N S
Gandham, Hima B
Kumari, Krishnaiah
Valluru, Krishna R
Nidasanametla, Satya K R
Battula, Venkateswara R
Namballa, Hari K
author_sort Adusumalli, Krishna M S
collection PubMed
description 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 functional group tolerance. Furthermore, the synthetic utility of this protocol was demonstrated in the successful synthesis of the antitumor agent CWJ-a-5 in gram scale.
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spelling pubmed-86092442021-12-06 Me(3)Al-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 Adusumalli, Krishna M S Konidena, Lakshmi N S Gandham, Hima B Kumari, Krishnaiah Valluru, Krishna R Nidasanametla, Satya K R Battula, Venkateswara R Namballa, Hari K Beilstein J Org Chem Letter 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 functional group tolerance. Furthermore, the synthetic utility of this protocol was demonstrated in the successful synthesis of the antitumor agent CWJ-a-5 in gram scale. Beilstein-Institut 2021-11-16 /pmc/articles/PMC8609244/ /pubmed/34876930 http://dx.doi.org/10.3762/bjoc.17.186 Text en Copyright © 2021, Adusumalli et al. https://creativecommons.org/licenses/by/4.0/https://www.beilstein-journals.org/bjoc/terms/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). Please note that the reuse, redistribution and reproduction in particular requires that the author(s) and source are credited and that individual graphics may be subject to special legal provisions. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms/terms)
spellingShingle Letter
Adusumalli, Krishna M S
Konidena, Lakshmi N S
Gandham, Hima B
Kumari, Krishnaiah
Valluru, Krishna R
Nidasanametla, Satya K R
Battula, Venkateswara R
Namballa, Hari K
Me(3)Al-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
title Me(3)Al-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
title_full Me(3)Al-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
title_fullStr Me(3)Al-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
title_full_unstemmed Me(3)Al-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
title_short Me(3)Al-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
title_sort me(3)al-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
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8609244/
https://www.ncbi.nlm.nih.gov/pubmed/34876930
http://dx.doi.org/10.3762/bjoc.17.186
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