Iron(III)-Catalyzed Synthesis of 2-Alkyl Homoallyl Sulfonyl Amides: Antiproliferative Study and Reactivity Scope of Aza-Prins Cyclization

Iron(III)-Catalyzed Synthesis of 2-Alkyl Homoallyl Sulfonyl Amides: Antiproliferative Study and Reactivity Scope of Aza-Prins Cyclization

A direct, catalytic, and complementary method to obtain 2-substituted homoallyl sulfonyl amides is described, starting from sulfonyl amides, aldehydes, and allyltrimethylsilane using iron(III) chloride as a sustainable catalyst. The scope of the process and the reactivity in aza-Prins cyclization is evaluated and supported by density functional theory (DFT) studies. Finally, an evaluation of the antiproliferative activity for this family of sulfonyl amides is also included.

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Main Authors: Carballo, Rubén M., Padrón, José M., Fernández, Israel, Cruz, Daniel A., Grmuša, Luana, Martín, Víctor S., Padrón, Juan I.
Other Authors: Ministerio de Ciencia e Innovación (España)
Format: artículo biblioteca
Language:English
Published: ACS Publications 2022-08-03
Subjects:Aldehydes, amides, carbene compounds, cyclization, piperidines,
Online Access:http://hdl.handle.net/10261/278954
http://dx.doi.org/10.13039/501100011033
http://dx.doi.org/10.13039/501100004837
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spelling dig-ipna-es-10261-2789542022-11-04T16:42:56Z Iron(III)-Catalyzed Synthesis of 2-Alkyl Homoallyl Sulfonyl Amides: Antiproliferative Study and Reactivity Scope of Aza-Prins Cyclization Carballo, Rubén M. Padrón, José M. Fernández, Israel Cruz, Daniel A. Grmuša, Luana Martín, Víctor S. Padrón, Juan I. Ministerio de Ciencia e Innovación (España) Agencia Estatal de Investigación (España) Cabildo de Tenerife Aldehydes amides carbene compounds cyclization piperidines A direct, catalytic, and complementary method to obtain 2-substituted homoallyl sulfonyl amides is described, starting from sulfonyl amides, aldehydes, and allyltrimethylsilane using iron(III) chloride as a sustainable catalyst. The scope of the process and the reactivity in aza-Prins cyclization is evaluated and supported by density functional theory (DFT) studies. Finally, an evaluation of the antiproliferative activity for this family of sulfonyl amides is also included. Grants (PGC2018-392094503-B-C22, CTQ2016-78205-P, and PID2019-106184GB-393-I00) funded by MCIN/AEI/ 10.13039/501100011033 and, as appropriate, by “ERDF A way of making Europe”, by the “European Union” or by the “European Union NextGenerationEU/PRTR”. V.S.M. thanks the Spanish MCIU for an FPU fellowship. D.A.C. thanks the Cabildo de Tenerife for a postdoctoral transfer contract and a Tenerife 2030 Programme (TF INNOVA 2016-2021) contract supported by the Marco Estratégico de Desarrollo Insular (MEDI) and Fondo de Desarrollo de Canarias (FDCAN). The text was revised by G. Jones, funded by the Cabildo de Tenerife from the same source under the same programme. I.F. is grateful for financial support from the Spanish MCIN/AEI/10.13039/501100011033 (Grants PID2019-106184GB-I00 and RED2018-102387-T). Peer reviewed 2022-09-12T12:50:33Z 2022-09-12T12:50:33Z 2022-08-03 artículo Journal of Organic Chemistry, 87(16), 11000–11006 (2022) 0022-3263 http://hdl.handle.net/10261/278954 10.1021/acs.joc.2c01267 1520-6904 http://dx.doi.org/10.13039/501100011033 http://dx.doi.org/10.13039/501100004837 en #PLACEHOLDER_PARENT_METADATA_VALUE# #PLACEHOLDER_PARENT_METADATA_VALUE# #PLACEHOLDER_PARENT_METADATA_VALUE# #PLACEHOLDER_PARENT_METADATA_VALUE# info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PGC2018-094503-B-C22/ES/QUIMICA SOSTENIBLE: DE MOLECULAS PEQUEÑAS A SISTEMAS FUNCIONALES COMPLEJAS/ info:eu-repo/grantAgreement/AEI/PROGRAMA ESTATAL DE FOMENTO DE LA INVESTIGACIÓN CIENTÍFICA Y TÉCNICA DE EXCELENCIA/CTQ2016-78205-P info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2019-106184GB-I00/ES/UNA APROXIMACION DIFERENTE PARA ENTENDER Y CONTROLAR LA CATALISIS/ info:eu-repo/grantAgreement/AEI/PROGRAMA ESTATAL DE GENERACIÓN DE CONOCIMIENTO Y FORTALECIMIENTO CIENTÍFICO Y TECNOLÓGICO DEL SISTEMA DE I+D+I/ RED2018‐102387‐T Publisher's version https://doi.org/10.1021/acs.joc.2c01267 Sí open ACS Publications
institution IPNA ES
collection DSpace
country España
countrycode ES
component Bibliográfico
access En linea
databasecode dig-ipna-es
tag biblioteca
region Europa del Sur
libraryname Biblioteca del IPNA España
language English
topic Aldehydes
amides
carbene compounds
cyclization
piperidines
Aldehydes
amides
carbene compounds
cyclization
piperidines
spellingShingle Aldehydes
amides
carbene compounds
cyclization
piperidines
Aldehydes
amides
carbene compounds
cyclization
piperidines
Carballo, Rubén M.
Padrón, José M.
Fernández, Israel
Cruz, Daniel A.
Grmuša, Luana
Martín, Víctor S.
Padrón, Juan I.
Iron(III)-Catalyzed Synthesis of 2-Alkyl Homoallyl Sulfonyl Amides: Antiproliferative Study and Reactivity Scope of Aza-Prins Cyclization
description A direct, catalytic, and complementary method to obtain 2-substituted homoallyl sulfonyl amides is described, starting from sulfonyl amides, aldehydes, and allyltrimethylsilane using iron(III) chloride as a sustainable catalyst. The scope of the process and the reactivity in aza-Prins cyclization is evaluated and supported by density functional theory (DFT) studies. Finally, an evaluation of the antiproliferative activity for this family of sulfonyl amides is also included.
author2 Ministerio de Ciencia e Innovación (España)
author_facet Ministerio de Ciencia e Innovación (España)
Carballo, Rubén M.
Padrón, José M.
Fernández, Israel
Cruz, Daniel A.
Grmuša, Luana
Martín, Víctor S.
Padrón, Juan I.
format artículo
topic_facet Aldehydes
amides
carbene compounds
cyclization
piperidines
author Carballo, Rubén M.
Padrón, José M.
Fernández, Israel
Cruz, Daniel A.
Grmuša, Luana
Martín, Víctor S.
Padrón, Juan I.
author_sort Carballo, Rubén M.
title Iron(III)-Catalyzed Synthesis of 2-Alkyl Homoallyl Sulfonyl Amides: Antiproliferative Study and Reactivity Scope of Aza-Prins Cyclization
title_short Iron(III)-Catalyzed Synthesis of 2-Alkyl Homoallyl Sulfonyl Amides: Antiproliferative Study and Reactivity Scope of Aza-Prins Cyclization
title_full Iron(III)-Catalyzed Synthesis of 2-Alkyl Homoallyl Sulfonyl Amides: Antiproliferative Study and Reactivity Scope of Aza-Prins Cyclization
title_fullStr Iron(III)-Catalyzed Synthesis of 2-Alkyl Homoallyl Sulfonyl Amides: Antiproliferative Study and Reactivity Scope of Aza-Prins Cyclization
title_full_unstemmed Iron(III)-Catalyzed Synthesis of 2-Alkyl Homoallyl Sulfonyl Amides: Antiproliferative Study and Reactivity Scope of Aza-Prins Cyclization
title_sort iron(iii)-catalyzed synthesis of 2-alkyl homoallyl sulfonyl amides: antiproliferative study and reactivity scope of aza-prins cyclization
publisher ACS Publications
publishDate 2022-08-03
url http://hdl.handle.net/10261/278954
http://dx.doi.org/10.13039/501100011033
http://dx.doi.org/10.13039/501100004837
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