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活化的螺环氮丙啶氧化吲哚与杂芳烃的开环环化反应:一种简便合成螺环氧化吲哚并吡咯并吲哚啉的方法。

Ring-opening cyclization of activated spiro-aziridine oxindoles with heteroarenes: a facile synthetic approach to spiro-oxindole-fused pyrroloindolines.

作者信息

Bhandari Sonal, Sana Sravani, Lahoti Vandana, Tokala Ramya, Shankaraiah Nagula

机构信息

Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER) Hyderabad-500037 India

出版信息

RSC Adv. 2020 Apr 24;10(27):16101-16109. doi: 10.1039/d0ra00684j. eCollection 2020 Apr 21.

DOI:10.1039/d0ra00684j
PMID:35493670
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9052938/
Abstract

Herein, we report a facile tandem approach for the synthesis of both spiro-oxindole-fused pyrroloindolines and benzofurano-pyrrolidines a Lewis acid-catalyzed domino ring-opening with concomitant ring annulation using activated spiro-aziridines and heteroarenes. This method offers a new class of novel spiro-fused polycyclic pyrrolidines in a one-pot and sustainable manner with good yields and high diastereoselectivity. In addition, the structure of 3d was confirmed by single X-ray crystallography analysis.

摘要

在此,我们报道了一种简便的串联方法,用于合成螺环氧化吲哚稠合的吡咯并吲哚啉和苯并呋喃并吡咯烷——一种使用活化的螺氮丙啶和杂芳烃的路易斯酸催化的多米诺开环并伴随环化反应。该方法以一锅法且可持续的方式提供了一类新型的螺稠合多环吡咯烷,产率良好且非对映选择性高。此外,通过单晶X射线晶体学分析确定了3d的结构。

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J Org Chem. 2018 Nov 16;83(22):14102-14109. doi: 10.1021/acs.joc.8b02117. Epub 2018 Oct 30.
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Mini Rev Med Chem. 2018;18(1):9-25. doi: 10.2174/1389557517666170807123201.
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Catalyst-Free "On-Water" Regio- and Stereospecific Ring-Opening of Spiroaziridine Oxindole: Enantiopure Synthesis of Unsymmetrical 3,3'-Bisindoles.
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