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3-亚烷基氧化吲哚与原位生成的α-芳基重氮甲烷的溶剂控制、可调多米诺反应：一种简便合成3-螺环丙基-2-氧化吲哚和吡唑并喹唑啉酮骨架的方法。

Solvent-Controlled, Tunable Domino Reaction of 3-Ylideneoxindoles with in Situ-Generated α-Aryldiazomethanes: A Facile Access to 3-Spirocyclopropyl-2-oxindole and Pyrazoloquinazolinone Scaffolds.

作者信息

Ramu Gopathi, Hari Krishna Namballa, Pawar Gaurav, Visweswara Sastry K N, Nanubolu Jagadeesh Babu, Nagendra Babu Bathini

机构信息

Department of Fluoro-Agrochemicals and Centre for X-ray Crystallography, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India.

Academy of Scientific and Innovative Research (AcSIR), New Delhi 110025, India.

出版信息

ACS Omega. 2018 Oct 1;3(10):12349-12360. doi: 10.1021/acsomega.8b01857. eCollection 2018 Oct 31.

DOI:10.1021/acsomega.8b01857
PMID:31457971
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6644904/
Abstract

A mild and efficient solvent-controlled, metal-free switchable 1,3-dipolar cycloaddition/ring contraction or ring expansion domino reaction of 3-ylideneoxindoles with in situ-generated α-aryldiazomethanes has been developed. This domino reaction provided a series of aryl-substituted 3-spirocyclopropyl-2-oxindoles and pyrazoloquinazolinones with excellent regio- and diastereoselectivity from common substrates under varying solvent conditions.

摘要

已开发出一种温和且高效的溶剂控制、无金属的可切换1,3-偶极环加成/环收缩或环扩展多米诺反应，该反应涉及3-亚烷基氧化吲哚与原位生成的α-芳基重氮甲烷。这种多米诺反应在不同的溶剂条件下，能从常见底物中以优异的区域和非对映选择性提供一系列芳基取代的3-螺环丙基-2-氧化吲哚和吡唑并喹唑啉酮。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/42a4/6644904/a7646d2bc1d8/ao-2018-01857n_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/42a4/6644904/8159d6eb59bc/ao-2018-01857n_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/42a4/6644904/33944e5246ea/ao-2018-01857n_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/42a4/6644904/a7646d2bc1d8/ao-2018-01857n_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/42a4/6644904/8159d6eb59bc/ao-2018-01857n_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/42a4/6644904/33944e5246ea/ao-2018-01857n_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/42a4/6644904/a7646d2bc1d8/ao-2018-01857n_0003.jpg

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本文引用的文献

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Synthesis of Spiro[pyrazolin-3,3'-oxindoles] and 3-Arylcarbonylmethyl Substituted Ylideneoxindoles by 1,3-Dipolar Cycloadditions of 3-Ylideneoxindoles and In-Situ-Generated α-Diazoketones.螺吡唑啉-3,3'-氧吲哚和 3-芳甲酰基取代亚烯基氧吲哚的合成通过 3-亚烯基氧吲哚与原位生成的α-重氮酮的 1,3-偶极环加成反应。
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Synthesis of Spiro[indazole-3,3'-indolin]-2'-ones via [3 + 2] Dipolar Cycloaddition of Arynes with 3-Diazoindolin-2-ones and Indazolo[2,3-c]quinazolin-6(5H)-ones by Subsequent Thermal Isomerization.通过芳炔与 3-重氮吲哚啉-2-酮和吲唑并[2,3-c]喹唑啉-6(5H)-酮的[3 + 2]偶极环加成反应及随后的热异构化合成螺[吲唑-3,3'-吲哚啉]-2'-酮
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