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Cascade alkylarylation of substituted N-allylbenzamides for the construction of dihydroisoquinolin-1(2H)-ones and isoquinoline-1,3(2H,4H)-diones

An oxidative reaction for the synthesis of 4-alkyl-substituted dihydroisoquinolin-1(2H)-ones with N-allylbenzamide derivatives as starting materials has been developed. The radical alkylarylation reaction proceeds through a sequence of alkylation and intramolecular cyclization. The substituent on th...

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Autores principales: Qian, Ping, Du, Bingnan, Jiao, Wei, Mei, Haibo, Han, Jianlin, Pan, Yi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4778529/
https://www.ncbi.nlm.nih.gov/pubmed/26977189
http://dx.doi.org/10.3762/bjoc.12.32
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author Qian, Ping
Du, Bingnan
Jiao, Wei
Mei, Haibo
Han, Jianlin
Pan, Yi
author_facet Qian, Ping
Du, Bingnan
Jiao, Wei
Mei, Haibo
Han, Jianlin
Pan, Yi
author_sort Qian, Ping
collection PubMed
description An oxidative reaction for the synthesis of 4-alkyl-substituted dihydroisoquinolin-1(2H)-ones with N-allylbenzamide derivatives as starting materials has been developed. The radical alkylarylation reaction proceeds through a sequence of alkylation and intramolecular cyclization. The substituent on the C–C double bond was found to play a key role for the progress of the reaction to give the expected products with good chemical yields. Additionally, N-methacryloylbenzamides were also suitable substrates for the current reaction and provided the alkyl-substituted isoquinoline-1,3(2H,4H)-diones in good yield.
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spelling pubmed-47785292016-03-14 Cascade alkylarylation of substituted N-allylbenzamides for the construction of dihydroisoquinolin-1(2H)-ones and isoquinoline-1,3(2H,4H)-diones Qian, Ping Du, Bingnan Jiao, Wei Mei, Haibo Han, Jianlin Pan, Yi Beilstein J Org Chem Full Research Paper An oxidative reaction for the synthesis of 4-alkyl-substituted dihydroisoquinolin-1(2H)-ones with N-allylbenzamide derivatives as starting materials has been developed. The radical alkylarylation reaction proceeds through a sequence of alkylation and intramolecular cyclization. The substituent on the C–C double bond was found to play a key role for the progress of the reaction to give the expected products with good chemical yields. Additionally, N-methacryloylbenzamides were also suitable substrates for the current reaction and provided the alkyl-substituted isoquinoline-1,3(2H,4H)-diones in good yield. Beilstein-Institut 2016-02-17 /pmc/articles/PMC4778529/ /pubmed/26977189 http://dx.doi.org/10.3762/bjoc.12.32 Text en Copyright © 2016, Qian et al. https://creativecommons.org/licenses/by/2.0https://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/2.0), 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
Qian, Ping
Du, Bingnan
Jiao, Wei
Mei, Haibo
Han, Jianlin
Pan, Yi
Cascade alkylarylation of substituted N-allylbenzamides for the construction of dihydroisoquinolin-1(2H)-ones and isoquinoline-1,3(2H,4H)-diones
title Cascade alkylarylation of substituted N-allylbenzamides for the construction of dihydroisoquinolin-1(2H)-ones and isoquinoline-1,3(2H,4H)-diones
title_full Cascade alkylarylation of substituted N-allylbenzamides for the construction of dihydroisoquinolin-1(2H)-ones and isoquinoline-1,3(2H,4H)-diones
title_fullStr Cascade alkylarylation of substituted N-allylbenzamides for the construction of dihydroisoquinolin-1(2H)-ones and isoquinoline-1,3(2H,4H)-diones
title_full_unstemmed Cascade alkylarylation of substituted N-allylbenzamides for the construction of dihydroisoquinolin-1(2H)-ones and isoquinoline-1,3(2H,4H)-diones
title_short Cascade alkylarylation of substituted N-allylbenzamides for the construction of dihydroisoquinolin-1(2H)-ones and isoquinoline-1,3(2H,4H)-diones
title_sort cascade alkylarylation of substituted n-allylbenzamides for the construction of dihydroisoquinolin-1(2h)-ones and isoquinoline-1,3(2h,4h)-diones
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4778529/
https://www.ncbi.nlm.nih.gov/pubmed/26977189
http://dx.doi.org/10.3762/bjoc.12.32
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