p-Nitrophenyl carbonate promoted ring-opening reactions of DBU and DBN affording lactam carbamates

The amidine bases DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) and DBN (1,5-diazabicyclo[4.3.0]non-5-ene) display nucleophilic behaviour towards highly electrophilic p-nitrophenyl carbonate derivatives with ring opening of the bicyclic ring to form corresponding substituted ε-caprolactam and γ-lactam de...

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Autores principales: Vangala, Madhuri, Shinde, Ganesh P
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2016
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5082618/
https://www.ncbi.nlm.nih.gov/pubmed/27829914
http://dx.doi.org/10.3762/bjoc.12.197
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author Vangala, Madhuri
Shinde, Ganesh P
author_facet Vangala, Madhuri
Shinde, Ganesh P
author_sort Vangala, Madhuri
collection PubMed
description The amidine bases DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) and DBN (1,5-diazabicyclo[4.3.0]non-5-ene) display nucleophilic behaviour towards highly electrophilic p-nitrophenyl carbonate derivatives with ring opening of the bicyclic ring to form corresponding substituted ε-caprolactam and γ-lactam derived carbamates. This simple method presents a unified strategy to synthesize structurally diverse ε-caprolactam and γ-lactam compounds with a large substrate scope.
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spelling pubmed-50826182016-11-09 p-Nitrophenyl carbonate promoted ring-opening reactions of DBU and DBN affording lactam carbamates Vangala, Madhuri Shinde, Ganesh P Beilstein J Org Chem Full Research Paper The amidine bases DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) and DBN (1,5-diazabicyclo[4.3.0]non-5-ene) display nucleophilic behaviour towards highly electrophilic p-nitrophenyl carbonate derivatives with ring opening of the bicyclic ring to form corresponding substituted ε-caprolactam and γ-lactam derived carbamates. This simple method presents a unified strategy to synthesize structurally diverse ε-caprolactam and γ-lactam compounds with a large substrate scope. Beilstein-Institut 2016-09-26 /pmc/articles/PMC5082618/ /pubmed/27829914 http://dx.doi.org/10.3762/bjoc.12.197 Text en Copyright © 2016, Vangala and Shinde https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Vangala, Madhuri
Shinde, Ganesh P
p-Nitrophenyl carbonate promoted ring-opening reactions of DBU and DBN affording lactam carbamates
title p-Nitrophenyl carbonate promoted ring-opening reactions of DBU and DBN affording lactam carbamates
title_full p-Nitrophenyl carbonate promoted ring-opening reactions of DBU and DBN affording lactam carbamates
title_fullStr p-Nitrophenyl carbonate promoted ring-opening reactions of DBU and DBN affording lactam carbamates
title_full_unstemmed p-Nitrophenyl carbonate promoted ring-opening reactions of DBU and DBN affording lactam carbamates
title_short p-Nitrophenyl carbonate promoted ring-opening reactions of DBU and DBN affording lactam carbamates
title_sort p-nitrophenyl carbonate promoted ring-opening reactions of dbu and dbn affording lactam carbamates
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5082618/
https://www.ncbi.nlm.nih.gov/pubmed/27829914
http://dx.doi.org/10.3762/bjoc.12.197
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AT shindeganeshp pnitrophenylcarbonatepromotedringopeningreactionsofdbuanddbnaffordinglactamcarbamates

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