Synthesis of Tetrahydroazepines through Silyl Aza-Prins Cyclization Mediated by Iron(III) Salts

[Image: see text] A new methodology for the synthesis of seven-membered unsaturated azacycles (tetrahydroazepines) was developed. It is based on the powerful aza-Prins cyclization in combination with the Peterson-type elimination reaction. In a single reaction step, a C–N, C–C bond and an endocyclic...

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Autores principales: Sinka, Victoria, Fernández, Israel, Padrón, Juan I.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9442639/
https://www.ncbi.nlm.nih.gov/pubmed/35977416
http://dx.doi.org/10.1021/acs.joc.2c01396
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author Sinka, Victoria
Fernández, Israel
Padrón, Juan I.
author_facet Sinka, Victoria
Fernández, Israel
Padrón, Juan I.
author_sort Sinka, Victoria
collection PubMed
description [Image: see text] A new methodology for the synthesis of seven-membered unsaturated azacycles (tetrahydroazepines) was developed. It is based on the powerful aza-Prins cyclization in combination with the Peterson-type elimination reaction. In a single reaction step, a C–N, C–C bond and an endocyclic double bond are formed. Under mild reaction conditions and using iron(III) salts as sustainable catalysts, tetrahydroazepines with different degrees of substitution are obtained directly and efficiently. DFT calculations supported the proposed mechanism.
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spelling pubmed-94426392022-09-06 Synthesis of Tetrahydroazepines through Silyl Aza-Prins Cyclization Mediated by Iron(III) Salts Sinka, Victoria Fernández, Israel Padrón, Juan I. J Org Chem [Image: see text] A new methodology for the synthesis of seven-membered unsaturated azacycles (tetrahydroazepines) was developed. It is based on the powerful aza-Prins cyclization in combination with the Peterson-type elimination reaction. In a single reaction step, a C–N, C–C bond and an endocyclic double bond are formed. Under mild reaction conditions and using iron(III) salts as sustainable catalysts, tetrahydroazepines with different degrees of substitution are obtained directly and efficiently. DFT calculations supported the proposed mechanism. American Chemical Society 2022-08-17 2022-09-02 /pmc/articles/PMC9442639/ /pubmed/35977416 http://dx.doi.org/10.1021/acs.joc.2c01396 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Sinka, Victoria
Fernández, Israel
Padrón, Juan I.
Synthesis of Tetrahydroazepines through Silyl Aza-Prins Cyclization Mediated by Iron(III) Salts
title Synthesis of Tetrahydroazepines through Silyl Aza-Prins Cyclization Mediated by Iron(III) Salts
title_full Synthesis of Tetrahydroazepines through Silyl Aza-Prins Cyclization Mediated by Iron(III) Salts
title_fullStr Synthesis of Tetrahydroazepines through Silyl Aza-Prins Cyclization Mediated by Iron(III) Salts
title_full_unstemmed Synthesis of Tetrahydroazepines through Silyl Aza-Prins Cyclization Mediated by Iron(III) Salts
title_short Synthesis of Tetrahydroazepines through Silyl Aza-Prins Cyclization Mediated by Iron(III) Salts
title_sort synthesis of tetrahydroazepines through silyl aza-prins cyclization mediated by iron(iii) salts
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9442639/
https://www.ncbi.nlm.nih.gov/pubmed/35977416
http://dx.doi.org/10.1021/acs.joc.2c01396
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