Microwave-assisted three-component domino reaction: Synthesis of indolodiazepinotriazoles

A microwave-assisted three-component protocol involving N-1 alkylation of 2-alkynylindoles with epichlorohydrin, ring opening of the epoxide with sodium azide, and an intramolecular Huisgen azide–internal alkyne 1,3-dipolar cycloaddition domino sequence has been described. The efficacy of the method...

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Autores principales: Arigela, Rajesh K, Sharma, Sudhir K, Kumar, Brijesh, Kundu, Bijoy
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2013
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3596043/
https://www.ncbi.nlm.nih.gov/pubmed/23504610
http://dx.doi.org/10.3762/bjoc.9.41
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author Arigela, Rajesh K
Sharma, Sudhir K
Kumar, Brijesh
Kundu, Bijoy
author_facet Arigela, Rajesh K
Sharma, Sudhir K
Kumar, Brijesh
Kundu, Bijoy
author_sort Arigela, Rajesh K
collection PubMed
description A microwave-assisted three-component protocol involving N-1 alkylation of 2-alkynylindoles with epichlorohydrin, ring opening of the epoxide with sodium azide, and an intramolecular Huisgen azide–internal alkyne 1,3-dipolar cycloaddition domino sequence has been described. The efficacy of the methodology has been demonstrated by treating various 2-alkynylindoles (aromatic/aliphatic) with epichlorohydrin and sodium azide furnishing annulated tetracyclic indolodiazepinotriazoles in satisfactory yields.
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spelling pubmed-35960432013-03-15 Microwave-assisted three-component domino reaction: Synthesis of indolodiazepinotriazoles Arigela, Rajesh K Sharma, Sudhir K Kumar, Brijesh Kundu, Bijoy Beilstein J Org Chem Full Research Paper A microwave-assisted three-component protocol involving N-1 alkylation of 2-alkynylindoles with epichlorohydrin, ring opening of the epoxide with sodium azide, and an intramolecular Huisgen azide–internal alkyne 1,3-dipolar cycloaddition domino sequence has been described. The efficacy of the methodology has been demonstrated by treating various 2-alkynylindoles (aromatic/aliphatic) with epichlorohydrin and sodium azide furnishing annulated tetracyclic indolodiazepinotriazoles in satisfactory yields. Beilstein-Institut 2013-02-19 /pmc/articles/PMC3596043/ /pubmed/23504610 http://dx.doi.org/10.3762/bjoc.9.41 Text en Copyright © 2013, Arigela 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
Arigela, Rajesh K
Sharma, Sudhir K
Kumar, Brijesh
Kundu, Bijoy
Microwave-assisted three-component domino reaction: Synthesis of indolodiazepinotriazoles
title Microwave-assisted three-component domino reaction: Synthesis of indolodiazepinotriazoles
title_full Microwave-assisted three-component domino reaction: Synthesis of indolodiazepinotriazoles
title_fullStr Microwave-assisted three-component domino reaction: Synthesis of indolodiazepinotriazoles
title_full_unstemmed Microwave-assisted three-component domino reaction: Synthesis of indolodiazepinotriazoles
title_short Microwave-assisted three-component domino reaction: Synthesis of indolodiazepinotriazoles
title_sort microwave-assisted three-component domino reaction: synthesis of indolodiazepinotriazoles
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3596043/
https://www.ncbi.nlm.nih.gov/pubmed/23504610
http://dx.doi.org/10.3762/bjoc.9.41
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