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MeAl介导的2-(2-氧代-2-苯乙基)苯甲腈与胺的多米诺亲核加成/分子内环化反应；一种合成取代1-氨基异喹啉的简便方法。

MeAl-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.

作者信息

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

机构信息

GVK Biosciences Private Limited, Medicinal Chemistry Laboratory, Hyderabad 500076, India.

Department of Engineering Chemistry, Andhra University College of Engineering (A), Andhra University, Visakhapatnam 530003, India.

出版信息

Beilstein J Org Chem. 2021 Nov 16;17:2765-2772. doi: 10.3762/bjoc.17.186. eCollection 2021.

DOI:10.3762/bjoc.17.186
PMID:34876930
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8609244/
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 MeAl. 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.

摘要

通过在甲基铝存在下用胺处理2-(2-氧代-2-苯乙基)苯甲腈，实现了一种简单高效的1-氨基异喹啉构建方法。该反应通过多米诺亲核加成随后进行分子内环化来进行。此方法能提供多种具有良好官能团耐受性的取代1-氨基异喹啉。此外，该方法的合成实用性在以克级规模成功合成抗肿瘤药物CWJ-a-5中得到了证明。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d7ee/8609244/9ddf93b58195/Beilstein_J_Org_Chem-17-2765-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d7ee/8609244/5b139b61f3fc/Beilstein_J_Org_Chem-17-2765-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d7ee/8609244/ee2a083340e0/Beilstein_J_Org_Chem-17-2765-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d7ee/8609244/5dddf5c61529/Beilstein_J_Org_Chem-17-2765-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d7ee/8609244/a79f38ffa9dc/Beilstein_J_Org_Chem-17-2765-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d7ee/8609244/4409034fee8a/Beilstein_J_Org_Chem-17-2765-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d7ee/8609244/9ddf93b58195/Beilstein_J_Org_Chem-17-2765-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d7ee/8609244/5b139b61f3fc/Beilstein_J_Org_Chem-17-2765-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d7ee/8609244/ee2a083340e0/Beilstein_J_Org_Chem-17-2765-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d7ee/8609244/5dddf5c61529/Beilstein_J_Org_Chem-17-2765-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d7ee/8609244/a79f38ffa9dc/Beilstein_J_Org_Chem-17-2765-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d7ee/8609244/4409034fee8a/Beilstein_J_Org_Chem-17-2765-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d7ee/8609244/9ddf93b58195/Beilstein_J_Org_Chem-17-2765-g007.jpg

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