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新型官能化噻唑并吡啶稠合和噻唑并吡啶嘧啶稠合螺环氧化吲哚的合成——一锅法反应

Synthesis of new functionalized thiazolo pyridine-fused and thiazolo pyridopyrimidine-fused spirooxindoles one-pot reactions.

作者信息

Nasri Shima, Bayat Mohammad, Farahani Hassan Vasheghani, Karami Solmaz

机构信息

Department of Chemistry, Faculty of Science, Imam Khomeini International University, Qazvin, Iran.

出版信息

Heliyon. 2020 Mar 31;6(3):e03687. doi: 10.1016/j.heliyon.2020.e03687. eCollection 2020 Mar.

DOI:10.1016/j.heliyon.2020.e03687
PMID:32258502
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7114753/
Abstract

A sequential multi-component reaction of the nitroketene dithioacetals, cysteamine hydrochloride, isatin and different CH-acids is described. This efficient method provides new functionalized thiazolo pyridine-fused spirooxindoles and thiazolo pyridopyrimidine-fused spirooxindoles in good yields. In the case of using isatin derivatives (5-bromoisatin and 5-chloroisatin), the reaction was carried out by using nano-SiO (20 mol%) as an effective heterogeneous Lewis acid promoter. This type of reaction provides a range of skeletally different polycyclic spiro thiazole-based heterocyclic structures and represents attractive advantages including straightforward one-pot operation under the catalyst-free condition and simple workup procedures without using tedious purification procedure.

摘要

本文描述了硝基乙烯酮二硫代缩醛、盐酸半胱胺、异吲哚酮和不同的碳氢键酸的连续多组分反应。这种高效方法能以良好产率提供新的官能化噻唑并吡啶稠合的螺环氧化吲哚和噻唑并吡啶嘧啶稠合的螺环氧化吲哚。在使用异吲哚酮衍生物(5-溴异吲哚酮和5-氯异吲哚酮)的情况下,反应通过使用纳米二氧化硅(20摩尔%)作为有效的多相路易斯酸促进剂进行。这类反应提供了一系列骨架不同的基于噻唑的多环螺环杂环结构,具有吸引人的优势,包括在无催化剂条件下直接一锅操作以及无需繁琐纯化步骤的简单后处理程序。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2986/7114753/0bd38c9ab832/gr5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2986/7114753/06d07852d379/gr1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2986/7114753/a3589c6860fd/gr2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2986/7114753/dc77489955ae/sc1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2986/7114753/704980882a2c/sc2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2986/7114753/3c91e9f17f54/gr3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2986/7114753/44fd73e02b17/sc3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2986/7114753/60ce3ebb69f2/gr4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2986/7114753/0bd38c9ab832/gr5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2986/7114753/06d07852d379/gr1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2986/7114753/a3589c6860fd/gr2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2986/7114753/dc77489955ae/sc1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2986/7114753/704980882a2c/sc2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2986/7114753/3c91e9f17f54/gr3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2986/7114753/44fd73e02b17/sc3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2986/7114753/60ce3ebb69f2/gr4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/2986/7114753/0bd38c9ab832/gr5.jpg

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Green synthesis of new pyrrolidine-fused spirooxindoles three-component domino reaction in EtOH/HO.新型吡咯烷稠合螺环氧化吲哚的绿色合成——在乙醇/水中的三组分多米诺反应
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