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Facile Synthesis of Tricyclic 1,2,4-Oxadiazolines-Fused Tetrahydro-Isoquinolines from Oxime Chlorides with 3,4-Dihydroisoquinoline Imines

A mild and efficient strategy for the synthesis of tricyclic 1,2,4-oxadiazolines-fused tetrahydro-isoquinolines derivatives via [3 + 2] cycloaddition reaction is reported. The reactions provided the functionalized tricyclic 1,2,4-oxadiazolines in high yields (up to 96%). This protocol is simple and...

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Detalles Bibliográficos
Autores principales: Wang, Kaikai, Li, Yanli, Zhang, Wei, Chen, Rongxiang, Ma, Xueji, Wang, Mingyue, Zhou, Nan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9145198/
https://www.ncbi.nlm.nih.gov/pubmed/35630538
http://dx.doi.org/10.3390/molecules27103064
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author Wang, Kaikai
Li, Yanli
Zhang, Wei
Chen, Rongxiang
Ma, Xueji
Wang, Mingyue
Zhou, Nan
author_facet Wang, Kaikai
Li, Yanli
Zhang, Wei
Chen, Rongxiang
Ma, Xueji
Wang, Mingyue
Zhou, Nan
author_sort Wang, Kaikai
collection PubMed
description A mild and efficient strategy for the synthesis of tricyclic 1,2,4-oxadiazolines-fused tetrahydro-isoquinolines derivatives via [3 + 2] cycloaddition reaction is reported. The reactions provided the functionalized tricyclic 1,2,4-oxadiazolines in high yields (up to 96%). This protocol is simple and easy to handle. Moreover, a gram-scale experiment further highlights the synthetic utility. The chemical structure of the product was determined by X-ray single-crystal structure analysis. A possible mechanism for this transformation is proposed to explain the reaction process.
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spelling pubmed-91451982022-05-29 Facile Synthesis of Tricyclic 1,2,4-Oxadiazolines-Fused Tetrahydro-Isoquinolines from Oxime Chlorides with 3,4-Dihydroisoquinoline Imines Wang, Kaikai Li, Yanli Zhang, Wei Chen, Rongxiang Ma, Xueji Wang, Mingyue Zhou, Nan Molecules Article A mild and efficient strategy for the synthesis of tricyclic 1,2,4-oxadiazolines-fused tetrahydro-isoquinolines derivatives via [3 + 2] cycloaddition reaction is reported. The reactions provided the functionalized tricyclic 1,2,4-oxadiazolines in high yields (up to 96%). This protocol is simple and easy to handle. Moreover, a gram-scale experiment further highlights the synthetic utility. The chemical structure of the product was determined by X-ray single-crystal structure analysis. A possible mechanism for this transformation is proposed to explain the reaction process. MDPI 2022-05-10 /pmc/articles/PMC9145198/ /pubmed/35630538 http://dx.doi.org/10.3390/molecules27103064 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Wang, Kaikai
Li, Yanli
Zhang, Wei
Chen, Rongxiang
Ma, Xueji
Wang, Mingyue
Zhou, Nan
Facile Synthesis of Tricyclic 1,2,4-Oxadiazolines-Fused Tetrahydro-Isoquinolines from Oxime Chlorides with 3,4-Dihydroisoquinoline Imines
title Facile Synthesis of Tricyclic 1,2,4-Oxadiazolines-Fused Tetrahydro-Isoquinolines from Oxime Chlorides with 3,4-Dihydroisoquinoline Imines
title_full Facile Synthesis of Tricyclic 1,2,4-Oxadiazolines-Fused Tetrahydro-Isoquinolines from Oxime Chlorides with 3,4-Dihydroisoquinoline Imines
title_fullStr Facile Synthesis of Tricyclic 1,2,4-Oxadiazolines-Fused Tetrahydro-Isoquinolines from Oxime Chlorides with 3,4-Dihydroisoquinoline Imines
title_full_unstemmed Facile Synthesis of Tricyclic 1,2,4-Oxadiazolines-Fused Tetrahydro-Isoquinolines from Oxime Chlorides with 3,4-Dihydroisoquinoline Imines
title_short Facile Synthesis of Tricyclic 1,2,4-Oxadiazolines-Fused Tetrahydro-Isoquinolines from Oxime Chlorides with 3,4-Dihydroisoquinoline Imines
title_sort facile synthesis of tricyclic 1,2,4-oxadiazolines-fused tetrahydro-isoquinolines from oxime chlorides with 3,4-dihydroisoquinoline imines
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9145198/
https://www.ncbi.nlm.nih.gov/pubmed/35630538
http://dx.doi.org/10.3390/molecules27103064
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