Chemo- and Stereoselective Synthesis of Substituted Thiazoles from tert-Alcohols Bearing Alkene and Alkyne Groups with Alkaline Earth Catalysts

[Image: see text] We report here that thioamides can distinguish C–C double bonds and C–C triple bonds chemoselectively when subjected to a reaction with pent-1-en-4-yn-3-ol derivatives in the presence of Ca(OTf)(2). This protocol offers a fast, efficient, and high-yielding synthesis of functionaliz...

Descripción completa

Detalles Bibliográficos
Autores principales: Yaragorla, Srinivasarao, Latha, Dandugula Sneha
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9520744/
https://www.ncbi.nlm.nih.gov/pubmed/36188313
http://dx.doi.org/10.1021/acsomega.2c05085
_version_ 1784799695304916992
author Yaragorla, Srinivasarao
Latha, Dandugula Sneha
author_facet Yaragorla, Srinivasarao
Latha, Dandugula Sneha
author_sort Yaragorla, Srinivasarao
collection PubMed
description [Image: see text] We report here that thioamides can distinguish C–C double bonds and C–C triple bonds chemoselectively when subjected to a reaction with pent-1-en-4-yn-3-ol derivatives in the presence of Ca(OTf)(2). This protocol offers a fast, efficient, and high-yielding synthesis of functionalized thiazoles. Interestingly, this reaction offers a time-dependent formation of kinetic and thermodynamic products. The products showed stereoselectivity concerning the alkene geometry. Further, we extended this protocol to synthesize oxazoles from propargyl alcohols and ibuprofen (NSAID) was converted into amide and then subjected to oxazole formation with tert-propargyl alcohols.
format Online
Article
Text
id pubmed-9520744
institution National Center for Biotechnology Information
language English
publishDate 2022
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-95207442022-09-30 Chemo- and Stereoselective Synthesis of Substituted Thiazoles from tert-Alcohols Bearing Alkene and Alkyne Groups with Alkaline Earth Catalysts Yaragorla, Srinivasarao Latha, Dandugula Sneha ACS Omega [Image: see text] We report here that thioamides can distinguish C–C double bonds and C–C triple bonds chemoselectively when subjected to a reaction with pent-1-en-4-yn-3-ol derivatives in the presence of Ca(OTf)(2). This protocol offers a fast, efficient, and high-yielding synthesis of functionalized thiazoles. Interestingly, this reaction offers a time-dependent formation of kinetic and thermodynamic products. The products showed stereoselectivity concerning the alkene geometry. Further, we extended this protocol to synthesize oxazoles from propargyl alcohols and ibuprofen (NSAID) was converted into amide and then subjected to oxazole formation with tert-propargyl alcohols. American Chemical Society 2022-09-15 /pmc/articles/PMC9520744/ /pubmed/36188313 http://dx.doi.org/10.1021/acsomega.2c05085 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Yaragorla, Srinivasarao
Latha, Dandugula Sneha
Chemo- and Stereoselective Synthesis of Substituted Thiazoles from tert-Alcohols Bearing Alkene and Alkyne Groups with Alkaline Earth Catalysts
title Chemo- and Stereoselective Synthesis of Substituted Thiazoles from tert-Alcohols Bearing Alkene and Alkyne Groups with Alkaline Earth Catalysts
title_full Chemo- and Stereoselective Synthesis of Substituted Thiazoles from tert-Alcohols Bearing Alkene and Alkyne Groups with Alkaline Earth Catalysts
title_fullStr Chemo- and Stereoselective Synthesis of Substituted Thiazoles from tert-Alcohols Bearing Alkene and Alkyne Groups with Alkaline Earth Catalysts
title_full_unstemmed Chemo- and Stereoselective Synthesis of Substituted Thiazoles from tert-Alcohols Bearing Alkene and Alkyne Groups with Alkaline Earth Catalysts
title_short Chemo- and Stereoselective Synthesis of Substituted Thiazoles from tert-Alcohols Bearing Alkene and Alkyne Groups with Alkaline Earth Catalysts
title_sort chemo- and stereoselective synthesis of substituted thiazoles from tert-alcohols bearing alkene and alkyne groups with alkaline earth catalysts
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9520744/
https://www.ncbi.nlm.nih.gov/pubmed/36188313
http://dx.doi.org/10.1021/acsomega.2c05085
work_keys_str_mv AT yaragorlasrinivasarao chemoandstereoselectivesynthesisofsubstitutedthiazolesfromtertalcoholsbearingalkeneandalkynegroupswithalkalineearthcatalysts
AT lathadandugulasneha chemoandstereoselectivesynthesisofsubstitutedthiazolesfromtertalcoholsbearingalkeneandalkynegroupswithalkalineearthcatalysts

Ejemplares similares