Formation of Synthetically Versatile 2-Aminobenzophenones from Readily Accessed Acyl Hydrazides

[Image: see text] Herein, we report the transformation of readily accessed acyl hydrazides into protected 2-aminobenzophenones via a two-step process involving an aryne-based molecular rearrangement followed by a one-pot addition–elimination procedure. The assembly of the scaffold is tolerant of a w...

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Autores principales: Ahmed, Nehaal, Shamsabadi, André, Chudasama, Vijay
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6941372/
https://www.ncbi.nlm.nih.gov/pubmed/31909344
http://dx.doi.org/10.1021/acsomega.9b03417
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author Ahmed, Nehaal
Shamsabadi, André
Chudasama, Vijay
author_facet Ahmed, Nehaal
Shamsabadi, André
Chudasama, Vijay
author_sort Ahmed, Nehaal
collection PubMed
description [Image: see text] Herein, we report the transformation of readily accessed acyl hydrazides into protected 2-aminobenzophenones via a two-step process involving an aryne-based molecular rearrangement followed by a one-pot addition–elimination procedure. The assembly of the scaffold is tolerant of a wide variety of functional groups, and the carbamate group on the product can be facilely removed to afford highly valuable 2-aminobenzophenones. Application of the protocol was demonstrated in the synthesis of neurological medicine phenazepam.
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spelling pubmed-69413722020-01-06 Formation of Synthetically Versatile 2-Aminobenzophenones from Readily Accessed Acyl Hydrazides Ahmed, Nehaal Shamsabadi, André Chudasama, Vijay ACS Omega [Image: see text] Herein, we report the transformation of readily accessed acyl hydrazides into protected 2-aminobenzophenones via a two-step process involving an aryne-based molecular rearrangement followed by a one-pot addition–elimination procedure. The assembly of the scaffold is tolerant of a wide variety of functional groups, and the carbamate group on the product can be facilely removed to afford highly valuable 2-aminobenzophenones. Application of the protocol was demonstrated in the synthesis of neurological medicine phenazepam. American Chemical Society 2019-12-17 /pmc/articles/PMC6941372/ /pubmed/31909344 http://dx.doi.org/10.1021/acsomega.9b03417 Text en Copyright © 2019 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Ahmed, Nehaal
Shamsabadi, André
Chudasama, Vijay
Formation of Synthetically Versatile 2-Aminobenzophenones from Readily Accessed Acyl Hydrazides
title Formation of Synthetically Versatile 2-Aminobenzophenones from Readily Accessed Acyl Hydrazides
title_full Formation of Synthetically Versatile 2-Aminobenzophenones from Readily Accessed Acyl Hydrazides
title_fullStr Formation of Synthetically Versatile 2-Aminobenzophenones from Readily Accessed Acyl Hydrazides
title_full_unstemmed Formation of Synthetically Versatile 2-Aminobenzophenones from Readily Accessed Acyl Hydrazides
title_short Formation of Synthetically Versatile 2-Aminobenzophenones from Readily Accessed Acyl Hydrazides
title_sort formation of synthetically versatile 2-aminobenzophenones from readily accessed acyl hydrazides
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6941372/
https://www.ncbi.nlm.nih.gov/pubmed/31909344
http://dx.doi.org/10.1021/acsomega.9b03417
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AT shamsabadiandre formationofsyntheticallyversatile2aminobenzophenonesfromreadilyaccessedacylhydrazides
AT chudasamavijay formationofsyntheticallyversatile2aminobenzophenonesfromreadilyaccessedacylhydrazides

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