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AgNTf(2)-catalyzed formal [3 + 2] cycloaddition of ynamides with unprotected isoxazol-5-amines: efficient access to functionalized 5-amino-1H-pyrrole-3-carboxamide derivatives

A formal [3 + 2] cycloaddition between ynamides and unprotected isoxazol-5-amines has been developed in the presence of catalytic AgNTf(2) in an open flask. By the protocol, a variety of functionalized 5-amino-1H-pyrrole-3-carboxamide derivatives can be obtained in up to 99% yield. The reaction mech...

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Autores principales: Cao, Ziping, Zhu, Jiekun, Liu, Li, Pang, Yuanling, Tian, Laijin, Sun, Xuejun, Meng, Xin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6880818/
https://www.ncbi.nlm.nih.gov/pubmed/31807197
http://dx.doi.org/10.3762/bjoc.15.255
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author Cao, Ziping
Zhu, Jiekun
Liu, Li
Pang, Yuanling
Tian, Laijin
Sun, Xuejun
Meng, Xin
author_facet Cao, Ziping
Zhu, Jiekun
Liu, Li
Pang, Yuanling
Tian, Laijin
Sun, Xuejun
Meng, Xin
author_sort Cao, Ziping
collection PubMed
description A formal [3 + 2] cycloaddition between ynamides and unprotected isoxazol-5-amines has been developed in the presence of catalytic AgNTf(2) in an open flask. By the protocol, a variety of functionalized 5-amino-1H-pyrrole-3-carboxamide derivatives can be obtained in up to 99% yield. The reaction mechanism might involve the generation of an unusual α-imino silver carbene intermediate (or a silver-stabilized carbocation) and subsequent cyclization/isomerization to build the significant pyrrole-3-carboxamide motif. The reaction features the use of an inexpensive catalyst, simple reaction conditions, simple work-up without column chromatographic purification for most of products and high yields.
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spelling pubmed-68808182019-12-05 AgNTf(2)-catalyzed formal [3 + 2] cycloaddition of ynamides with unprotected isoxazol-5-amines: efficient access to functionalized 5-amino-1H-pyrrole-3-carboxamide derivatives Cao, Ziping Zhu, Jiekun Liu, Li Pang, Yuanling Tian, Laijin Sun, Xuejun Meng, Xin Beilstein J Org Chem Full Research Paper A formal [3 + 2] cycloaddition between ynamides and unprotected isoxazol-5-amines has been developed in the presence of catalytic AgNTf(2) in an open flask. By the protocol, a variety of functionalized 5-amino-1H-pyrrole-3-carboxamide derivatives can be obtained in up to 99% yield. The reaction mechanism might involve the generation of an unusual α-imino silver carbene intermediate (or a silver-stabilized carbocation) and subsequent cyclization/isomerization to build the significant pyrrole-3-carboxamide motif. The reaction features the use of an inexpensive catalyst, simple reaction conditions, simple work-up without column chromatographic purification for most of products and high yields. Beilstein-Institut 2019-11-04 /pmc/articles/PMC6880818/ /pubmed/31807197 http://dx.doi.org/10.3762/bjoc.15.255 Text en Copyright © 2019, Cao et al. https://creativecommons.org/licenses/by/4.0https://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/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. 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
Cao, Ziping
Zhu, Jiekun
Liu, Li
Pang, Yuanling
Tian, Laijin
Sun, Xuejun
Meng, Xin
AgNTf(2)-catalyzed formal [3 + 2] cycloaddition of ynamides with unprotected isoxazol-5-amines: efficient access to functionalized 5-amino-1H-pyrrole-3-carboxamide derivatives
title AgNTf(2)-catalyzed formal [3 + 2] cycloaddition of ynamides with unprotected isoxazol-5-amines: efficient access to functionalized 5-amino-1H-pyrrole-3-carboxamide derivatives
title_full AgNTf(2)-catalyzed formal [3 + 2] cycloaddition of ynamides with unprotected isoxazol-5-amines: efficient access to functionalized 5-amino-1H-pyrrole-3-carboxamide derivatives
title_fullStr AgNTf(2)-catalyzed formal [3 + 2] cycloaddition of ynamides with unprotected isoxazol-5-amines: efficient access to functionalized 5-amino-1H-pyrrole-3-carboxamide derivatives
title_full_unstemmed AgNTf(2)-catalyzed formal [3 + 2] cycloaddition of ynamides with unprotected isoxazol-5-amines: efficient access to functionalized 5-amino-1H-pyrrole-3-carboxamide derivatives
title_short AgNTf(2)-catalyzed formal [3 + 2] cycloaddition of ynamides with unprotected isoxazol-5-amines: efficient access to functionalized 5-amino-1H-pyrrole-3-carboxamide derivatives
title_sort agntf(2)-catalyzed formal [3 + 2] cycloaddition of ynamides with unprotected isoxazol-5-amines: efficient access to functionalized 5-amino-1h-pyrrole-3-carboxamide derivatives
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6880818/
https://www.ncbi.nlm.nih.gov/pubmed/31807197
http://dx.doi.org/10.3762/bjoc.15.255
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