An efficient synthesis of N-substituted 3-nitrothiophen-2-amines

A novel protocol for the synthesis of 3-nitro-N-aryl/alkylthiophen-2-amines in good yields from the reaction of α-nitroketene N,S-aryl/alkylaminoacetals and 1,4-dithiane-2,5-diol in the presence of K(2)CO(3) in refluxing ethanol is described. This transformation generates two C–C bonds in a single o...

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Autores principales: Vivek Kumar, Sundaravel, Muthusubramanian, Shanmugam, Menéndez, J Carlos, Perumal, Subbu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2015
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4660920/
https://www.ncbi.nlm.nih.gov/pubmed/26664589
http://dx.doi.org/10.3762/bjoc.11.185
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author Vivek Kumar, Sundaravel
Muthusubramanian, Shanmugam
Menéndez, J Carlos
Perumal, Subbu
author_facet Vivek Kumar, Sundaravel
Muthusubramanian, Shanmugam
Menéndez, J Carlos
Perumal, Subbu
author_sort Vivek Kumar, Sundaravel
collection PubMed
description A novel protocol for the synthesis of 3-nitro-N-aryl/alkylthiophen-2-amines in good yields from the reaction of α-nitroketene N,S-aryl/alkylaminoacetals and 1,4-dithiane-2,5-diol in the presence of K(2)CO(3) in refluxing ethanol is described. This transformation generates two C–C bonds in a single operation and presumably proceeds through a reaction sequence comprising 2-mercaptoacetaldehyde generation, nucleophilic carbonyl addition, annelation and elimination steps.
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spelling pubmed-46609202015-12-09 An efficient synthesis of N-substituted 3-nitrothiophen-2-amines Vivek Kumar, Sundaravel Muthusubramanian, Shanmugam Menéndez, J Carlos Perumal, Subbu Beilstein J Org Chem Full Research Paper A novel protocol for the synthesis of 3-nitro-N-aryl/alkylthiophen-2-amines in good yields from the reaction of α-nitroketene N,S-aryl/alkylaminoacetals and 1,4-dithiane-2,5-diol in the presence of K(2)CO(3) in refluxing ethanol is described. This transformation generates two C–C bonds in a single operation and presumably proceeds through a reaction sequence comprising 2-mercaptoacetaldehyde generation, nucleophilic carbonyl addition, annelation and elimination steps. Beilstein-Institut 2015-09-22 /pmc/articles/PMC4660920/ /pubmed/26664589 http://dx.doi.org/10.3762/bjoc.11.185 Text en Copyright © 2015, Vivek Kumar et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Vivek Kumar, Sundaravel
Muthusubramanian, Shanmugam
Menéndez, J Carlos
Perumal, Subbu
An efficient synthesis of N-substituted 3-nitrothiophen-2-amines
title An efficient synthesis of N-substituted 3-nitrothiophen-2-amines
title_full An efficient synthesis of N-substituted 3-nitrothiophen-2-amines
title_fullStr An efficient synthesis of N-substituted 3-nitrothiophen-2-amines
title_full_unstemmed An efficient synthesis of N-substituted 3-nitrothiophen-2-amines
title_short An efficient synthesis of N-substituted 3-nitrothiophen-2-amines
title_sort efficient synthesis of n-substituted 3-nitrothiophen-2-amines
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4660920/
https://www.ncbi.nlm.nih.gov/pubmed/26664589
http://dx.doi.org/10.3762/bjoc.11.185
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