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

  1. Midhun Sai Krishna Adusumalli,
  2. Lakshmi Narayana Sharma Konidena,
  3. Hima Bindu Gandham,
  4. Krishnaiah Kumari,
  5. Krishna Reddy Valluru,
  6. Satya Kameswara Rao NidasanametlaORCID Logo,
  7. Venkateswara Rao Battula and
  8. Hari Krishna NamballaORCID Logo

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

  • Preprint

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

Supporting Information

Format: DOCX Size: 1.4 MB   Download

How to Cite

When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

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

Download Citation
Download RIS (Reference Manager) Download BIB (BIBTEX)

© 2021 Adusumalli et al.; licensee Beilstein-Institut.
This is an open access work under the terms of the Creative Commons Attribution License (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 Archives terms and conditions: (https://www.beilstein-archives.org/xiv/terms)

Other Beilstein-Institut Open Science Activities

Logo
Logo
Logo
Symposia