DMAP-Catalyzed One-Pot Synthesis of Quinazoline-2,4-diones from 2-Aminobenzamides and Di-tert-butyl Dicarbonate

[Image: see text] The one-pot synthesis of quinazoline-2,4-diones was developed in the presence of 4-dimethylaminopyridine (DMAP) by metal-free catalysis. The commercially available (Boc)(2)O acted as a key precursor in the construction of the 2-position carbonyl of quinazolinediones. The p-methoxyb...

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Autores principales: Chen, Hui, Li, Peng, Qin, Rongfei, Yan, Hong, Li, Gang, Huang, Haihong
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7191844/
https://www.ncbi.nlm.nih.gov/pubmed/32363314
http://dx.doi.org/10.1021/acsomega.0c01104
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author Chen, Hui
Li, Peng
Qin, Rongfei
Yan, Hong
Li, Gang
Huang, Haihong
author_facet Chen, Hui
Li, Peng
Qin, Rongfei
Yan, Hong
Li, Gang
Huang, Haihong
author_sort Chen, Hui
collection PubMed
description [Image: see text] The one-pot synthesis of quinazoline-2,4-diones was developed in the presence of 4-dimethylaminopyridine (DMAP) by metal-free catalysis. The commercially available (Boc)(2)O acted as a key precursor in the construction of the 2-position carbonyl of quinazolinediones. The p-methoxybenzyl (PMB)-activated heterocyclization could smoothly proceed at room temperature instead of the microwave condition. This strategy is compatible with a variety of substrates with different functional groups. Furthermore, this protocol was utilized to smoothly prepare Zenarestat with a total yield of 70%.
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spelling pubmed-71918442020-05-01 DMAP-Catalyzed One-Pot Synthesis of Quinazoline-2,4-diones from 2-Aminobenzamides and Di-tert-butyl Dicarbonate Chen, Hui Li, Peng Qin, Rongfei Yan, Hong Li, Gang Huang, Haihong ACS Omega [Image: see text] The one-pot synthesis of quinazoline-2,4-diones was developed in the presence of 4-dimethylaminopyridine (DMAP) by metal-free catalysis. The commercially available (Boc)(2)O acted as a key precursor in the construction of the 2-position carbonyl of quinazolinediones. The p-methoxybenzyl (PMB)-activated heterocyclization could smoothly proceed at room temperature instead of the microwave condition. This strategy is compatible with a variety of substrates with different functional groups. Furthermore, this protocol was utilized to smoothly prepare Zenarestat with a total yield of 70%. American Chemical Society 2020-04-16 /pmc/articles/PMC7191844/ /pubmed/32363314 http://dx.doi.org/10.1021/acsomega.0c01104 Text en Copyright © 2020 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Chen, Hui
Li, Peng
Qin, Rongfei
Yan, Hong
Li, Gang
Huang, Haihong
DMAP-Catalyzed One-Pot Synthesis of Quinazoline-2,4-diones from 2-Aminobenzamides and Di-tert-butyl Dicarbonate
title DMAP-Catalyzed One-Pot Synthesis of Quinazoline-2,4-diones from 2-Aminobenzamides and Di-tert-butyl Dicarbonate
title_full DMAP-Catalyzed One-Pot Synthesis of Quinazoline-2,4-diones from 2-Aminobenzamides and Di-tert-butyl Dicarbonate
title_fullStr DMAP-Catalyzed One-Pot Synthesis of Quinazoline-2,4-diones from 2-Aminobenzamides and Di-tert-butyl Dicarbonate
title_full_unstemmed DMAP-Catalyzed One-Pot Synthesis of Quinazoline-2,4-diones from 2-Aminobenzamides and Di-tert-butyl Dicarbonate
title_short DMAP-Catalyzed One-Pot Synthesis of Quinazoline-2,4-diones from 2-Aminobenzamides and Di-tert-butyl Dicarbonate
title_sort dmap-catalyzed one-pot synthesis of quinazoline-2,4-diones from 2-aminobenzamides and di-tert-butyl dicarbonate
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7191844/
https://www.ncbi.nlm.nih.gov/pubmed/32363314
http://dx.doi.org/10.1021/acsomega.0c01104
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