Synthesis of a-chlorolactams by cyanoborohydride-mediated radical cyclization of trichloroacetamides

A cyanoborohydride-promoted radical cyclization methodology has been developed to access α-chlorolactams in a simple and efficient way, using NaBH3CN and trichloroacetamides easily available from allylic and homoallylic secondary amines. This methodology allowed the synthesis of a library of αchloro...

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Detalles Bibliográficos
Autores: Coussanes, Guilhem, Jakobi, Harald, Lindell, Stephen, Bonjoch i Sesé, Josep
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2018
País:España
Institución:Universidad de Barcelona
Repositorio:Dipòsit Digital de la UB
OAI Identifier:oai:diposit.ub.edu:2445/128198
Acceso en línea:https://hdl.handle.net/2445/128198
Access Level:acceso abierto
Palabra clave:Lactames
Herbicides
Radicals (Química)
Síntesi orgànica
Lactams
Radicals (Chemistry)
Organic synthesis
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spelling Synthesis of a-chlorolactams by cyanoborohydride-mediated radical cyclization of trichloroacetamidesCoussanes, GuilhemJakobi, HaraldLindell, StephenBonjoch i Sesé, JosepLactamesHerbicidesRadicals (Química)Síntesi orgànicaLactamsHerbicidesRadicals (Chemistry)Organic synthesisA cyanoborohydride-promoted radical cyclization methodology has been developed to access α-chlorolactams in a simple and efficient way, using NaBH3CN and trichloroacetamides easily available from allylic and homoallylic secondary amines. This methodology allowed the synthesis of a library of αchlorolactams (mono and bicyclic), which were tested for herbicidal activity, trans-3-chloro-4-methyl-1-(3-trifluoromethyl)phenyl-2-pyrrolidinone being the most active.Wiley-VCH2018info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersionapplication/pdfhttps://hdl.handle.net/2445/128198Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)reponame:Dipòsit Digital de la UBinstname:Universidad de BarcelonaInglésVersió postprint del document publicat a: https://doi.org/10.1002/chem.201800210Chemistry-A European Journal, 2018, vol. 24, num. 32, p. 8151-8156https://doi.org/10.1002/chem.201800210(c) Wiley-VCH, 2018info:eu-repo/semantics/openAccessoai:diposit.ub.edu:2445/1281982026-05-27T06:46:51Z
dc.title.none.fl_str_mv Synthesis of a-chlorolactams by cyanoborohydride-mediated radical cyclization of trichloroacetamides
title Synthesis of a-chlorolactams by cyanoborohydride-mediated radical cyclization of trichloroacetamides
spellingShingle Synthesis of a-chlorolactams by cyanoborohydride-mediated radical cyclization of trichloroacetamides
Coussanes, Guilhem
Lactames
Herbicides
Radicals (Química)
Síntesi orgànica
Lactams
Herbicides
Radicals (Chemistry)
Organic synthesis
title_short Synthesis of a-chlorolactams by cyanoborohydride-mediated radical cyclization of trichloroacetamides
title_full Synthesis of a-chlorolactams by cyanoborohydride-mediated radical cyclization of trichloroacetamides
title_fullStr Synthesis of a-chlorolactams by cyanoborohydride-mediated radical cyclization of trichloroacetamides
title_full_unstemmed Synthesis of a-chlorolactams by cyanoborohydride-mediated radical cyclization of trichloroacetamides
title_sort Synthesis of a-chlorolactams by cyanoborohydride-mediated radical cyclization of trichloroacetamides
dc.creator.none.fl_str_mv Coussanes, Guilhem
Jakobi, Harald
Lindell, Stephen
Bonjoch i Sesé, Josep
author Coussanes, Guilhem
author_facet Coussanes, Guilhem
Jakobi, Harald
Lindell, Stephen
Bonjoch i Sesé, Josep
author_role author
author2 Jakobi, Harald
Lindell, Stephen
Bonjoch i Sesé, Josep
author2_role author
author
author
dc.subject.none.fl_str_mv Lactames
Herbicides
Radicals (Química)
Síntesi orgànica
Lactams
Herbicides
Radicals (Chemistry)
Organic synthesis
topic Lactames
Herbicides
Radicals (Química)
Síntesi orgànica
Lactams
Herbicides
Radicals (Chemistry)
Organic synthesis
description A cyanoborohydride-promoted radical cyclization methodology has been developed to access α-chlorolactams in a simple and efficient way, using NaBH3CN and trichloroacetamides easily available from allylic and homoallylic secondary amines. This methodology allowed the synthesis of a library of αchlorolactams (mono and bicyclic), which were tested for herbicidal activity, trans-3-chloro-4-methyl-1-(3-trifluoromethyl)phenyl-2-pyrrolidinone being the most active.
publishDate 2018
dc.date.none.fl_str_mv 2018
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv https://hdl.handle.net/2445/128198
url https://hdl.handle.net/2445/128198
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Versió postprint del document publicat a: https://doi.org/10.1002/chem.201800210
Chemistry-A European Journal, 2018, vol. 24, num. 32, p. 8151-8156
https://doi.org/10.1002/chem.201800210
dc.rights.none.fl_str_mv (c) Wiley-VCH, 2018
info:eu-repo/semantics/openAccess
rights_invalid_str_mv (c) Wiley-VCH, 2018
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Wiley-VCH
publisher.none.fl_str_mv Wiley-VCH
dc.source.none.fl_str_mv Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)
reponame:Dipòsit Digital de la UB
instname:Universidad de Barcelona
instname_str Universidad de Barcelona
reponame_str Dipòsit Digital de la UB
collection Dipòsit Digital de la UB
repository.name.fl_str_mv
repository.mail.fl_str_mv
_version_ 1869412658697994240
score 15.301629

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