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Efficient Rapid Access to Biginelli for the Multicomponent Synthesis of 1,2,3,4-Tetrahydropyrimidines in Room-Temperature Diisopropyl Ethyl Ammonium Acetate

[Image: see text] The diisopropyl ethyl ammonium acetate (DIPEAc)-promoted Biginelli protocol has been developed for the first time by a successive one-pot three-component reaction of aldehydes, ethylcyanoacetate/ethyl acetoacetate, and thiourea/urea to afford pharmacologically promising 1,2,3,4-tet...

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Autores principales: Jadhav, Chetan K., Nipate, Amol S., Chate, Asha V., Songire, Vishal D., Patil, Anil P., Gill, Charansingh. H.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6941212/
https://www.ncbi.nlm.nih.gov/pubmed/31909314
http://dx.doi.org/10.1021/acsomega.9b02286
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author Jadhav, Chetan K.
Nipate, Amol S.
Chate, Asha V.
Songire, Vishal D.
Patil, Anil P.
Gill, Charansingh. H.
author_facet Jadhav, Chetan K.
Nipate, Amol S.
Chate, Asha V.
Songire, Vishal D.
Patil, Anil P.
Gill, Charansingh. H.
author_sort Jadhav, Chetan K.
collection PubMed
description [Image: see text] The diisopropyl ethyl ammonium acetate (DIPEAc)-promoted Biginelli protocol has been developed for the first time by a successive one-pot three-component reaction of aldehydes, ethylcyanoacetate/ethyl acetoacetate, and thiourea/urea to afford pharmacologically promising 1,2,3,4-tetrahydropyrimidines in high yields at room temperature. The key benefits of the present scheme are the capability to allow a variability of functional groups, short reaction times, easy workup, high yields, recyclability of the catalyst, and solvent-free conditions, thus providing economic and environmental advantages. In addition, a series of 4-oxo-6-aryl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitriles analogues were synthesized and selected for their in vitro antifungal and antibacterial activities.
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spelling pubmed-69412122020-01-06 Efficient Rapid Access to Biginelli for the Multicomponent Synthesis of 1,2,3,4-Tetrahydropyrimidines in Room-Temperature Diisopropyl Ethyl Ammonium Acetate Jadhav, Chetan K. Nipate, Amol S. Chate, Asha V. Songire, Vishal D. Patil, Anil P. Gill, Charansingh. H. ACS Omega [Image: see text] The diisopropyl ethyl ammonium acetate (DIPEAc)-promoted Biginelli protocol has been developed for the first time by a successive one-pot three-component reaction of aldehydes, ethylcyanoacetate/ethyl acetoacetate, and thiourea/urea to afford pharmacologically promising 1,2,3,4-tetrahydropyrimidines in high yields at room temperature. The key benefits of the present scheme are the capability to allow a variability of functional groups, short reaction times, easy workup, high yields, recyclability of the catalyst, and solvent-free conditions, thus providing economic and environmental advantages. In addition, a series of 4-oxo-6-aryl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitriles analogues were synthesized and selected for their in vitro antifungal and antibacterial activities. American Chemical Society 2019-12-17 /pmc/articles/PMC6941212/ /pubmed/31909314 http://dx.doi.org/10.1021/acsomega.9b02286 Text en Copyright © 2019 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Jadhav, Chetan K.
Nipate, Amol S.
Chate, Asha V.
Songire, Vishal D.
Patil, Anil P.
Gill, Charansingh. H.
Efficient Rapid Access to Biginelli for the Multicomponent Synthesis of 1,2,3,4-Tetrahydropyrimidines in Room-Temperature Diisopropyl Ethyl Ammonium Acetate
title Efficient Rapid Access to Biginelli for the Multicomponent Synthesis of 1,2,3,4-Tetrahydropyrimidines in Room-Temperature Diisopropyl Ethyl Ammonium Acetate
title_full Efficient Rapid Access to Biginelli for the Multicomponent Synthesis of 1,2,3,4-Tetrahydropyrimidines in Room-Temperature Diisopropyl Ethyl Ammonium Acetate
title_fullStr Efficient Rapid Access to Biginelli for the Multicomponent Synthesis of 1,2,3,4-Tetrahydropyrimidines in Room-Temperature Diisopropyl Ethyl Ammonium Acetate
title_full_unstemmed Efficient Rapid Access to Biginelli for the Multicomponent Synthesis of 1,2,3,4-Tetrahydropyrimidines in Room-Temperature Diisopropyl Ethyl Ammonium Acetate
title_short Efficient Rapid Access to Biginelli for the Multicomponent Synthesis of 1,2,3,4-Tetrahydropyrimidines in Room-Temperature Diisopropyl Ethyl Ammonium Acetate
title_sort efficient rapid access to biginelli for the multicomponent synthesis of 1,2,3,4-tetrahydropyrimidines in room-temperature diisopropyl ethyl ammonium acetate
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6941212/
https://www.ncbi.nlm.nih.gov/pubmed/31909314
http://dx.doi.org/10.1021/acsomega.9b02286
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