One-pot double annulations to confer diastereoselective spirooxindolepyrrolothiazoles

A novel four-component reaction in one pot as an atom- and step-economic process was developed to synthesize diastereoselectively spirooxindolepyrrolothiazoles through sequential N,S-acetalation of aldehydes with cysteine and decarboxylative [3 + 2] cycloaddition with olefinic oxindoles. High synthe...

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Detalles Bibliográficos
Autores principales: Lu, Juan, Yao, Bin, Zhan, Desheng, Sun, Zhuo, Ji, Yun, Zhang, Xiaofeng
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2022
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9727273/
https://www.ncbi.nlm.nih.gov/pubmed/36530533
http://dx.doi.org/10.3762/bjoc.18.171
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author Lu, Juan
Yao, Bin
Zhan, Desheng
Sun, Zhuo
Ji, Yun
Zhang, Xiaofeng
author_facet Lu, Juan
Yao, Bin
Zhan, Desheng
Sun, Zhuo
Ji, Yun
Zhang, Xiaofeng
author_sort Lu, Juan
collection PubMed
description A novel four-component reaction in one pot as an atom- and step-economic process was developed to synthesize diastereoselectively spirooxindolepyrrolothiazoles through sequential N,S-acetalation of aldehydes with cysteine and decarboxylative [3 + 2] cycloaddition with olefinic oxindoles. High synthetic efficiency, operational simplification and reaction process economy using EtOH as solvent, and only releasing CO(2) and H(2)O as side products confer this approach favorable in green chemistry metrics analysis.
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spelling pubmed-97272732022-12-16 One-pot double annulations to confer diastereoselective spirooxindolepyrrolothiazoles Lu, Juan Yao, Bin Zhan, Desheng Sun, Zhuo Ji, Yun Zhang, Xiaofeng Beilstein J Org Chem Full Research Paper A novel four-component reaction in one pot as an atom- and step-economic process was developed to synthesize diastereoselectively spirooxindolepyrrolothiazoles through sequential N,S-acetalation of aldehydes with cysteine and decarboxylative [3 + 2] cycloaddition with olefinic oxindoles. High synthetic efficiency, operational simplification and reaction process economy using EtOH as solvent, and only releasing CO(2) and H(2)O as side products confer this approach favorable in green chemistry metrics analysis. Beilstein-Institut 2022-11-28 /pmc/articles/PMC9727273/ /pubmed/36530533 http://dx.doi.org/10.3762/bjoc.18.171 Text en Copyright © 2022, Lu et al. https://creativecommons.org/licenses/by/4.0/This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.
spellingShingle Full Research Paper
Lu, Juan
Yao, Bin
Zhan, Desheng
Sun, Zhuo
Ji, Yun
Zhang, Xiaofeng
One-pot double annulations to confer diastereoselective spirooxindolepyrrolothiazoles
title One-pot double annulations to confer diastereoselective spirooxindolepyrrolothiazoles
title_full One-pot double annulations to confer diastereoselective spirooxindolepyrrolothiazoles
title_fullStr One-pot double annulations to confer diastereoselective spirooxindolepyrrolothiazoles
title_full_unstemmed One-pot double annulations to confer diastereoselective spirooxindolepyrrolothiazoles
title_short One-pot double annulations to confer diastereoselective spirooxindolepyrrolothiazoles
title_sort one-pot double annulations to confer diastereoselective spirooxindolepyrrolothiazoles
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9727273/
https://www.ncbi.nlm.nih.gov/pubmed/36530533
http://dx.doi.org/10.3762/bjoc.18.171
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