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在环境友好条件下通过简便的一锅多组分反应合成螺环氧化吲哚并噻喃衍生物。

Facile one-pot, multi-component reaction to synthesize spirooxindole-annulated thiopyran derivatives under environmentally benevolent conditions.

作者信息

Matloubi Moghaddam F, Aghamiri Bagher

机构信息

Laboratory of Organic Synthesis and Natural Products, Department of Chemistry, Sharif University of Technology, Azadi Street, PO Box 111559516, Tehran, Iran.

出版信息

Heliyon. 2022 Sep 20;8(9):e10666. doi: 10.1016/j.heliyon.2022.e10666. eCollection 2022 Sep.

DOI:10.1016/j.heliyon.2022.e10666
PMID:36185147
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9520212/
Abstract

An efficient and facile one-pot, five-component reaction for the synthesis of 2,6-diamino-1-alkyl-2-oxospiro[indoline-3,4'-thiopyran]-3,5-dicarbonitrile derivatives has been reported by a reaction between primary amines, carbon disulfide, malononitrile, and isatin derivatives. The major advantages of this procedure are high yields of products in relatively short reaction time, scalability, mild conditions, multi-component synthetic procedure, low catalyst loading, no column separation and simple reaction work-up. As a consequence, this synthetic procedure provided an efficient access to spirooxindole-annulated thiopyran derivatives.

摘要

据报道,通过伯胺、二硫化碳、丙二腈和异吲哚酮衍生物之间的反应,可实现一种高效简便的一锅法五组分反应,用于合成2,6-二氨基-1-烷基-2-氧代螺[吲哚啉-3,4'-硫吡喃]-3,5-二腈衍生物。该方法的主要优点是在相对较短的反应时间内产物收率高、可扩展性强、条件温和、多组分合成步骤、催化剂负载量低、无需柱分离且反应后处理简单。因此,该合成方法为合成螺环氧化吲哚并硫吡喃衍生物提供了一条有效途径。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2a54/9520212/be9191a27ebc/sc2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2a54/9520212/1f91166d9dfe/ga1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2a54/9520212/b721c952dd22/sc1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2a54/9520212/be9191a27ebc/sc2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2a54/9520212/1f91166d9dfe/ga1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2a54/9520212/b721c952dd22/sc1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2a54/9520212/be9191a27ebc/sc2.jpg

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Synthesis of spiro-tetrahydrothiopyran-oxindoles by Michael-aldol cascade reactions: discovery of potential P53-MDM2 inhibitors with good antitumor activity.
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