Synthesis of 3-(phenylazo)-1,2,4-triazoles by a nucleophilic reaction of primary amines with 5-chloro-2,3-diphenyltetrazolium salt via mesoionic 2,3-diphenyltetrazolium-5-aminides

The reactions of a 5-chloro-2,3-diphenyltetrazolium salt with amines have been examined. In the presence of an inorganic base such as NaHCO(3), primary and secondary amines undergo a nucleophilic substitution to give the corresponding 5-aminotetrazolium salts. When triethylamine is used as a base, p...

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Autores principales: Araki, Shuki, Hirose, Satoshi, Konishi, Yoshikazu, Nogura, Masatoshi, Hirashita, Tsunehisa
Formato: Texto
Lenguaje:English
Publicado: Beilstein-Institut 2009
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2686317/
https://www.ncbi.nlm.nih.gov/pubmed/19478914
http://dx.doi.org/10.3762/bjoc.5.8
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author Araki, Shuki
Hirose, Satoshi
Konishi, Yoshikazu
Nogura, Masatoshi
Hirashita, Tsunehisa
author_facet Araki, Shuki
Hirose, Satoshi
Konishi, Yoshikazu
Nogura, Masatoshi
Hirashita, Tsunehisa
author_sort Araki, Shuki
collection PubMed
description The reactions of a 5-chloro-2,3-diphenyltetrazolium salt with amines have been examined. In the presence of an inorganic base such as NaHCO(3), primary and secondary amines undergo a nucleophilic substitution to give the corresponding 5-aminotetrazolium salts. When triethylamine is used as a base, primary amines give 3-phenylazo-1,2,4-triazoles. A plausible dual-path mechanism is proposed for the formation of the triazoles via Type B mesoionic tetrazolium-5-aminides.
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spelling pubmed-26863172009-05-28 Synthesis of 3-(phenylazo)-1,2,4-triazoles by a nucleophilic reaction of primary amines with 5-chloro-2,3-diphenyltetrazolium salt via mesoionic 2,3-diphenyltetrazolium-5-aminides Araki, Shuki Hirose, Satoshi Konishi, Yoshikazu Nogura, Masatoshi Hirashita, Tsunehisa Beilstein J Org Chem Full Research Paper The reactions of a 5-chloro-2,3-diphenyltetrazolium salt with amines have been examined. In the presence of an inorganic base such as NaHCO(3), primary and secondary amines undergo a nucleophilic substitution to give the corresponding 5-aminotetrazolium salts. When triethylamine is used as a base, primary amines give 3-phenylazo-1,2,4-triazoles. A plausible dual-path mechanism is proposed for the formation of the triazoles via Type B mesoionic tetrazolium-5-aminides. Beilstein-Institut 2009-03-02 /pmc/articles/PMC2686317/ /pubmed/19478914 http://dx.doi.org/10.3762/bjoc.5.8 Text en Copyright © 2009, Araki 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
Araki, Shuki
Hirose, Satoshi
Konishi, Yoshikazu
Nogura, Masatoshi
Hirashita, Tsunehisa
Synthesis of 3-(phenylazo)-1,2,4-triazoles by a nucleophilic reaction of primary amines with 5-chloro-2,3-diphenyltetrazolium salt via mesoionic 2,3-diphenyltetrazolium-5-aminides
title Synthesis of 3-(phenylazo)-1,2,4-triazoles by a nucleophilic reaction of primary amines with 5-chloro-2,3-diphenyltetrazolium salt via mesoionic 2,3-diphenyltetrazolium-5-aminides
title_full Synthesis of 3-(phenylazo)-1,2,4-triazoles by a nucleophilic reaction of primary amines with 5-chloro-2,3-diphenyltetrazolium salt via mesoionic 2,3-diphenyltetrazolium-5-aminides
title_fullStr Synthesis of 3-(phenylazo)-1,2,4-triazoles by a nucleophilic reaction of primary amines with 5-chloro-2,3-diphenyltetrazolium salt via mesoionic 2,3-diphenyltetrazolium-5-aminides
title_full_unstemmed Synthesis of 3-(phenylazo)-1,2,4-triazoles by a nucleophilic reaction of primary amines with 5-chloro-2,3-diphenyltetrazolium salt via mesoionic 2,3-diphenyltetrazolium-5-aminides
title_short Synthesis of 3-(phenylazo)-1,2,4-triazoles by a nucleophilic reaction of primary amines with 5-chloro-2,3-diphenyltetrazolium salt via mesoionic 2,3-diphenyltetrazolium-5-aminides
title_sort synthesis of 3-(phenylazo)-1,2,4-triazoles by a nucleophilic reaction of primary amines with 5-chloro-2,3-diphenyltetrazolium salt via mesoionic 2,3-diphenyltetrazolium-5-aminides
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2686317/
https://www.ncbi.nlm.nih.gov/pubmed/19478914
http://dx.doi.org/10.3762/bjoc.5.8
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