Facile Synthesis of Pyrrolyl 4-Quinolinone Alkaloid Quinolactacide by 9-AJ-Catalyzed Tandem Acyl Transfer–Cyclization of o-Alkynoylaniline Derivatives

[Image: see text] The synthesis of pyrrolyl 4-quinolinone alkaloid, quinolactacide, and its analogues was successfully achieved using 9-azajulolidine (9-AJ)-catalyzed tandem acyl transfer–regioselective cyclization of N,N-diacyl-o-alkynoylaniline derivatives. In addition, this organocatalytic reacti...

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Autores principales: Saito, Koya, Yoshida, Masahito, Uekusa, Hidehiro, Doi, Takayuki
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2017
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6641763/
https://www.ncbi.nlm.nih.gov/pubmed/31457730
http://dx.doi.org/10.1021/acsomega.7b00793
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author Saito, Koya
Yoshida, Masahito
Uekusa, Hidehiro
Doi, Takayuki
author_facet Saito, Koya
Yoshida, Masahito
Uekusa, Hidehiro
Doi, Takayuki
author_sort Saito, Koya
collection PubMed
description [Image: see text] The synthesis of pyrrolyl 4-quinolinone alkaloid, quinolactacide, and its analogues was successfully achieved using 9-azajulolidine (9-AJ)-catalyzed tandem acyl transfer–regioselective cyclization of N,N-diacyl-o-alkynoylaniline derivatives. In addition, this organocatalytic reaction was successfully utilized for the synthesis of a variety of 3-acyl-4-quinolinones in moderate-to-good yields. Mechanistic studies, including a time course nuclear magnetic resonance (NMR) experiment, indicated that the 1,4-addition of 9-AJ to an ynone system can be considered to be the rate-determining step in this quinolinone synthesis.
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spelling pubmed-66417632019-08-27 Facile Synthesis of Pyrrolyl 4-Quinolinone Alkaloid Quinolactacide by 9-AJ-Catalyzed Tandem Acyl Transfer–Cyclization of o-Alkynoylaniline Derivatives Saito, Koya Yoshida, Masahito Uekusa, Hidehiro Doi, Takayuki ACS Omega [Image: see text] The synthesis of pyrrolyl 4-quinolinone alkaloid, quinolactacide, and its analogues was successfully achieved using 9-azajulolidine (9-AJ)-catalyzed tandem acyl transfer–regioselective cyclization of N,N-diacyl-o-alkynoylaniline derivatives. In addition, this organocatalytic reaction was successfully utilized for the synthesis of a variety of 3-acyl-4-quinolinones in moderate-to-good yields. Mechanistic studies, including a time course nuclear magnetic resonance (NMR) experiment, indicated that the 1,4-addition of 9-AJ to an ynone system can be considered to be the rate-determining step in this quinolinone synthesis. American Chemical Society 2017-08-09 /pmc/articles/PMC6641763/ /pubmed/31457730 http://dx.doi.org/10.1021/acsomega.7b00793 Text en Copyright © 2017 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 Saito, Koya
Yoshida, Masahito
Uekusa, Hidehiro
Doi, Takayuki
Facile Synthesis of Pyrrolyl 4-Quinolinone Alkaloid Quinolactacide by 9-AJ-Catalyzed Tandem Acyl Transfer–Cyclization of o-Alkynoylaniline Derivatives
title Facile Synthesis of Pyrrolyl 4-Quinolinone Alkaloid Quinolactacide by 9-AJ-Catalyzed Tandem Acyl Transfer–Cyclization of o-Alkynoylaniline Derivatives
title_full Facile Synthesis of Pyrrolyl 4-Quinolinone Alkaloid Quinolactacide by 9-AJ-Catalyzed Tandem Acyl Transfer–Cyclization of o-Alkynoylaniline Derivatives
title_fullStr Facile Synthesis of Pyrrolyl 4-Quinolinone Alkaloid Quinolactacide by 9-AJ-Catalyzed Tandem Acyl Transfer–Cyclization of o-Alkynoylaniline Derivatives
title_full_unstemmed Facile Synthesis of Pyrrolyl 4-Quinolinone Alkaloid Quinolactacide by 9-AJ-Catalyzed Tandem Acyl Transfer–Cyclization of o-Alkynoylaniline Derivatives
title_short Facile Synthesis of Pyrrolyl 4-Quinolinone Alkaloid Quinolactacide by 9-AJ-Catalyzed Tandem Acyl Transfer–Cyclization of o-Alkynoylaniline Derivatives
title_sort facile synthesis of pyrrolyl 4-quinolinone alkaloid quinolactacide by 9-aj-catalyzed tandem acyl transfer–cyclization of o-alkynoylaniline derivatives
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6641763/
https://www.ncbi.nlm.nih.gov/pubmed/31457730
http://dx.doi.org/10.1021/acsomega.7b00793
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