Hypervalent iodine-mediated Ritter-type amidation of terminal alkenes: The synthesis of isoxazoline and pyrazoline cores

Hypervalent iodine-mediated olefin functionalization provides a rapid gateway towards accessing both various heterocyclic cores and functional groups. In this regard, we have developed a Ritter-type alkene functionalization utilizing a PhI(OAc)(2) ((diacetoxyiodo)benzene, PIDA)/Lewis acid combinatio...

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Autores principales: Park, Sang Won, Kim, Soong-Hyun, Song, Jaeyoung, Park, Ga Young, Kim, Darong, Nam, Tae-Gyu, Hong, Ki Bum
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2018
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6009250/
https://www.ncbi.nlm.nih.gov/pubmed/29977375
http://dx.doi.org/10.3762/bjoc.14.89
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author Park, Sang Won
Kim, Soong-Hyun
Song, Jaeyoung
Park, Ga Young
Kim, Darong
Nam, Tae-Gyu
Hong, Ki Bum
author_facet Park, Sang Won
Kim, Soong-Hyun
Song, Jaeyoung
Park, Ga Young
Kim, Darong
Nam, Tae-Gyu
Hong, Ki Bum
author_sort Park, Sang Won
collection PubMed
description Hypervalent iodine-mediated olefin functionalization provides a rapid gateway towards accessing both various heterocyclic cores and functional groups. In this regard, we have developed a Ritter-type alkene functionalization utilizing a PhI(OAc)(2) ((diacetoxyiodo)benzene, PIDA)/Lewis acid combination in order to access isoxazoline and pyrazoline cores. Based on allyl ketone oximes and allyl ketone tosylhydrazones, we have developed an alkene oxyamidation and amido-amidation protocol en route to accessing both isoxazoline and pyrazoline cores. Additionally, acetonitrile serves as both the solvent and an amine source in the presence of this PIDA/Lewis acid combination. This operationally straightforward and metal-free protocol provides an easy access to isoxazoline and pyrazoline derivatives.
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spelling pubmed-60092502018-07-05 Hypervalent iodine-mediated Ritter-type amidation of terminal alkenes: The synthesis of isoxazoline and pyrazoline cores Park, Sang Won Kim, Soong-Hyun Song, Jaeyoung Park, Ga Young Kim, Darong Nam, Tae-Gyu Hong, Ki Bum Beilstein J Org Chem Letter Hypervalent iodine-mediated olefin functionalization provides a rapid gateway towards accessing both various heterocyclic cores and functional groups. In this regard, we have developed a Ritter-type alkene functionalization utilizing a PhI(OAc)(2) ((diacetoxyiodo)benzene, PIDA)/Lewis acid combination in order to access isoxazoline and pyrazoline cores. Based on allyl ketone oximes and allyl ketone tosylhydrazones, we have developed an alkene oxyamidation and amido-amidation protocol en route to accessing both isoxazoline and pyrazoline cores. Additionally, acetonitrile serves as both the solvent and an amine source in the presence of this PIDA/Lewis acid combination. This operationally straightforward and metal-free protocol provides an easy access to isoxazoline and pyrazoline derivatives. Beilstein-Institut 2018-05-11 /pmc/articles/PMC6009250/ /pubmed/29977375 http://dx.doi.org/10.3762/bjoc.14.89 Text en Copyright © 2018, Park 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), 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 Letter
Park, Sang Won
Kim, Soong-Hyun
Song, Jaeyoung
Park, Ga Young
Kim, Darong
Nam, Tae-Gyu
Hong, Ki Bum
Hypervalent iodine-mediated Ritter-type amidation of terminal alkenes: The synthesis of isoxazoline and pyrazoline cores
title Hypervalent iodine-mediated Ritter-type amidation of terminal alkenes: The synthesis of isoxazoline and pyrazoline cores
title_full Hypervalent iodine-mediated Ritter-type amidation of terminal alkenes: The synthesis of isoxazoline and pyrazoline cores
title_fullStr Hypervalent iodine-mediated Ritter-type amidation of terminal alkenes: The synthesis of isoxazoline and pyrazoline cores
title_full_unstemmed Hypervalent iodine-mediated Ritter-type amidation of terminal alkenes: The synthesis of isoxazoline and pyrazoline cores
title_short Hypervalent iodine-mediated Ritter-type amidation of terminal alkenes: The synthesis of isoxazoline and pyrazoline cores
title_sort hypervalent iodine-mediated ritter-type amidation of terminal alkenes: the synthesis of isoxazoline and pyrazoline cores
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6009250/
https://www.ncbi.nlm.nih.gov/pubmed/29977375
http://dx.doi.org/10.3762/bjoc.14.89
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