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α-Hydroxy acid as an aldehyde surrogate: metal-free synthesis of pyrrolo[1,2-a]quinoxalines, quinazolinones, and other N-heterocycles via decarboxylative oxidative annulation reaction

A metal-free and efficient procedure for the synthesis of pyrrolo[1,2-a]quinoxalines, quinazolinones, and indolo[1,2-a]quinoxaline has been developed. The key features of our method include the in situ generation of aldehyde from α-hydroxy acid in the presence of TBHP (tert-butyl hydrogen peroxide),...

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Autores principales: Viji, Mayavan, Vishwanath, Manjunatha, Sim, Jaeuk, Park, Yunjeong, Jung, Chanhyun, Lee, Seohu, Lee, Heesoon, Lee, Kiho, Jung, Jae-Kyung
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9057147/
https://www.ncbi.nlm.nih.gov/pubmed/35521290
http://dx.doi.org/10.1039/d0ra07093a
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author Viji, Mayavan
Vishwanath, Manjunatha
Sim, Jaeuk
Park, Yunjeong
Jung, Chanhyun
Lee, Seohu
Lee, Heesoon
Lee, Kiho
Jung, Jae-Kyung
author_facet Viji, Mayavan
Vishwanath, Manjunatha
Sim, Jaeuk
Park, Yunjeong
Jung, Chanhyun
Lee, Seohu
Lee, Heesoon
Lee, Kiho
Jung, Jae-Kyung
author_sort Viji, Mayavan
collection PubMed
description A metal-free and efficient procedure for the synthesis of pyrrolo[1,2-a]quinoxalines, quinazolinones, and indolo[1,2-a]quinoxaline has been developed. The key features of our method include the in situ generation of aldehyde from α-hydroxy acid in the presence of TBHP (tert-butyl hydrogen peroxide), and further condensation with various amines, followed by intramolecular cyclization and subsequent oxidation to afford the corresponding quinoxalines, quinazolinones derivatives in moderate to high yields.
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spelling pubmed-90571472022-05-04 α-Hydroxy acid as an aldehyde surrogate: metal-free synthesis of pyrrolo[1,2-a]quinoxalines, quinazolinones, and other N-heterocycles via decarboxylative oxidative annulation reaction Viji, Mayavan Vishwanath, Manjunatha Sim, Jaeuk Park, Yunjeong Jung, Chanhyun Lee, Seohu Lee, Heesoon Lee, Kiho Jung, Jae-Kyung RSC Adv Chemistry A metal-free and efficient procedure for the synthesis of pyrrolo[1,2-a]quinoxalines, quinazolinones, and indolo[1,2-a]quinoxaline has been developed. The key features of our method include the in situ generation of aldehyde from α-hydroxy acid in the presence of TBHP (tert-butyl hydrogen peroxide), and further condensation with various amines, followed by intramolecular cyclization and subsequent oxidation to afford the corresponding quinoxalines, quinazolinones derivatives in moderate to high yields. The Royal Society of Chemistry 2020-10-07 /pmc/articles/PMC9057147/ /pubmed/35521290 http://dx.doi.org/10.1039/d0ra07093a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Viji, Mayavan
Vishwanath, Manjunatha
Sim, Jaeuk
Park, Yunjeong
Jung, Chanhyun
Lee, Seohu
Lee, Heesoon
Lee, Kiho
Jung, Jae-Kyung
α-Hydroxy acid as an aldehyde surrogate: metal-free synthesis of pyrrolo[1,2-a]quinoxalines, quinazolinones, and other N-heterocycles via decarboxylative oxidative annulation reaction
title α-Hydroxy acid as an aldehyde surrogate: metal-free synthesis of pyrrolo[1,2-a]quinoxalines, quinazolinones, and other N-heterocycles via decarboxylative oxidative annulation reaction
title_full α-Hydroxy acid as an aldehyde surrogate: metal-free synthesis of pyrrolo[1,2-a]quinoxalines, quinazolinones, and other N-heterocycles via decarboxylative oxidative annulation reaction
title_fullStr α-Hydroxy acid as an aldehyde surrogate: metal-free synthesis of pyrrolo[1,2-a]quinoxalines, quinazolinones, and other N-heterocycles via decarboxylative oxidative annulation reaction
title_full_unstemmed α-Hydroxy acid as an aldehyde surrogate: metal-free synthesis of pyrrolo[1,2-a]quinoxalines, quinazolinones, and other N-heterocycles via decarboxylative oxidative annulation reaction
title_short α-Hydroxy acid as an aldehyde surrogate: metal-free synthesis of pyrrolo[1,2-a]quinoxalines, quinazolinones, and other N-heterocycles via decarboxylative oxidative annulation reaction
title_sort α-hydroxy acid as an aldehyde surrogate: metal-free synthesis of pyrrolo[1,2-a]quinoxalines, quinazolinones, and other n-heterocycles via decarboxylative oxidative annulation reaction
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9057147/
https://www.ncbi.nlm.nih.gov/pubmed/35521290
http://dx.doi.org/10.1039/d0ra07093a
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