A modified Beckmann rearrangement for the facile synthesis of amidines and imidates via imidoyl fluoride intermediates

Herein, we report a modified Beckmann rearrangement using sulfone iminium fluoride (SIF) reagents to rapidly synthesize imidoyl fluoride intermediates. Subsequently, amidine and imidate products can be formed following the introduction of amine and alcohol nucleophiles, respectively. Overall, approx...

Descripción completa

Detalles Bibliográficos
Autores principales: Vogel, James A., Miller, Kirya F., Shin, Eunjeong, Krussman, Jenna M., Melvin, Patrick R.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10573916/
https://www.ncbi.nlm.nih.gov/pubmed/37842679
http://dx.doi.org/10.1039/d3ra06561h
_version_ 1785120572402827264
author Vogel, James A.
Miller, Kirya F.
Shin, Eunjeong
Krussman, Jenna M.
Melvin, Patrick R.
author_facet Vogel, James A.
Miller, Kirya F.
Shin, Eunjeong
Krussman, Jenna M.
Melvin, Patrick R.
author_sort Vogel, James A.
collection PubMed
description Herein, we report a modified Beckmann rearrangement using sulfone iminium fluoride (SIF) reagents to rapidly synthesize imidoyl fluoride intermediates. Subsequently, amidine and imidate products can be formed following the introduction of amine and alcohol nucleophiles, respectively. Overall, approximately 50 amidine and imidate products have been isolated in high yields utilizing mild conditions.
format Online
Article
Text
id pubmed-10573916
institution National Center for Biotechnology Information
language English
publishDate 2023
publisher The Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-105739162023-10-14 A modified Beckmann rearrangement for the facile synthesis of amidines and imidates via imidoyl fluoride intermediates Vogel, James A. Miller, Kirya F. Shin, Eunjeong Krussman, Jenna M. Melvin, Patrick R. RSC Adv Chemistry Herein, we report a modified Beckmann rearrangement using sulfone iminium fluoride (SIF) reagents to rapidly synthesize imidoyl fluoride intermediates. Subsequently, amidine and imidate products can be formed following the introduction of amine and alcohol nucleophiles, respectively. Overall, approximately 50 amidine and imidate products have been isolated in high yields utilizing mild conditions. The Royal Society of Chemistry 2023-10-13 /pmc/articles/PMC10573916/ /pubmed/37842679 http://dx.doi.org/10.1039/d3ra06561h Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Vogel, James A.
Miller, Kirya F.
Shin, Eunjeong
Krussman, Jenna M.
Melvin, Patrick R.
A modified Beckmann rearrangement for the facile synthesis of amidines and imidates via imidoyl fluoride intermediates
title A modified Beckmann rearrangement for the facile synthesis of amidines and imidates via imidoyl fluoride intermediates
title_full A modified Beckmann rearrangement for the facile synthesis of amidines and imidates via imidoyl fluoride intermediates
title_fullStr A modified Beckmann rearrangement for the facile synthesis of amidines and imidates via imidoyl fluoride intermediates
title_full_unstemmed A modified Beckmann rearrangement for the facile synthesis of amidines and imidates via imidoyl fluoride intermediates
title_short A modified Beckmann rearrangement for the facile synthesis of amidines and imidates via imidoyl fluoride intermediates
title_sort modified beckmann rearrangement for the facile synthesis of amidines and imidates via imidoyl fluoride intermediates
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10573916/
https://www.ncbi.nlm.nih.gov/pubmed/37842679
http://dx.doi.org/10.1039/d3ra06561h
work_keys_str_mv AT vogeljamesa amodifiedbeckmannrearrangementforthefacilesynthesisofamidinesandimidatesviaimidoylfluorideintermediates
AT millerkiryaf amodifiedbeckmannrearrangementforthefacilesynthesisofamidinesandimidatesviaimidoylfluorideintermediates
AT shineunjeong amodifiedbeckmannrearrangementforthefacilesynthesisofamidinesandimidatesviaimidoylfluorideintermediates
AT krussmanjennam amodifiedbeckmannrearrangementforthefacilesynthesisofamidinesandimidatesviaimidoylfluorideintermediates
AT melvinpatrickr amodifiedbeckmannrearrangementforthefacilesynthesisofamidinesandimidatesviaimidoylfluorideintermediates
AT vogeljamesa modifiedbeckmannrearrangementforthefacilesynthesisofamidinesandimidatesviaimidoylfluorideintermediates
AT millerkiryaf modifiedbeckmannrearrangementforthefacilesynthesisofamidinesandimidatesviaimidoylfluorideintermediates
AT shineunjeong modifiedbeckmannrearrangementforthefacilesynthesisofamidinesandimidatesviaimidoylfluorideintermediates
AT krussmanjennam modifiedbeckmannrearrangementforthefacilesynthesisofamidinesandimidatesviaimidoylfluorideintermediates
AT melvinpatrickr modifiedbeckmannrearrangementforthefacilesynthesisofamidinesandimidatesviaimidoylfluorideintermediates

Ejemplares similares