One-pot Synthesis of 6-Aza-chromone Derivatives Through Cascade Carbonylation-Sonogashira-Cyclization

One-pot Synthesis of 6-Aza-chromone Derivatives Through Cascade Carbonylation-Sonogashira-Cyclization

Abstract We developed an efficient synthesis of aza-chromones from 3-iodo-4-(1H)-pyridones and terminal acetylenes via a cascade carbonylation-Sonogashira-cyclization reaction. By controlling the use of bases, both 6-aza-chromones 5 and 3-(4-oxo-1,4-dihydroquinoline-3-carbonyl)-4H-pyrano[3,2-c]quino...

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Main Authors: Gang Cheng, Yingbei Qi, Xiaoqian Zhou, Rong Sheng, Yong-Zhou Hu, Youhong Hu
Format: Article
Language:English
Published: Nature Publishing Group 2017-06-01
Series:Scientific Reports
Online Access:https://doi.org/10.1038/s41598-017-04693-7
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spelling doaj-e2290e184752452ab45873be86b563b72020-12-08T02:51:03ZengNature Publishing GroupScientific Reports2045-23222017-06-01711710.1038/s41598-017-04693-7One-pot Synthesis of 6-Aza-chromone Derivatives Through Cascade Carbonylation-Sonogashira-CyclizationGang Cheng0Yingbei Qi1Xiaoqian Zhou2Rong Sheng3Yong-Zhou Hu4Youhong Hu5College of Pharmaceutical Sciences, Zhejiang UniversityCollege of Pharmaceutical Sciences, Zhejiang UniversityCollege of Pharmaceutical Sciences, Zhejiang UniversityCollege of Pharmaceutical Sciences, Zhejiang UniversityCollege of Pharmaceutical Sciences, Zhejiang UniversityState Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of SciencesAbstract We developed an efficient synthesis of aza-chromones from 3-iodo-4-(1H)-pyridones and terminal acetylenes via a cascade carbonylation-Sonogashira-cyclization reaction. By controlling the use of bases, both 6-aza-chromones 5 and 3-(4-oxo-1,4-dihydroquinoline-3-carbonyl)-4H-pyrano[3,2-c]quinolin-4-ones 6 could be selectively obtained in moderate to good yields.https://doi.org/10.1038/s41598-017-04693-7
collection DOAJ
language English
format Article
sources DOAJ
author Gang Cheng
Yingbei Qi
Xiaoqian Zhou
Rong Sheng
Yong-Zhou Hu
Youhong Hu
spellingShingle Gang Cheng
Yingbei Qi
Xiaoqian Zhou
Rong Sheng
Yong-Zhou Hu
Youhong Hu
One-pot Synthesis of 6-Aza-chromone Derivatives Through Cascade Carbonylation-Sonogashira-Cyclization
Scientific Reports
author_facet Gang Cheng
Yingbei Qi
Xiaoqian Zhou
Rong Sheng
Yong-Zhou Hu
Youhong Hu
author_sort Gang Cheng
title One-pot Synthesis of 6-Aza-chromone Derivatives Through Cascade Carbonylation-Sonogashira-Cyclization
title_short One-pot Synthesis of 6-Aza-chromone Derivatives Through Cascade Carbonylation-Sonogashira-Cyclization
title_full One-pot Synthesis of 6-Aza-chromone Derivatives Through Cascade Carbonylation-Sonogashira-Cyclization
title_fullStr One-pot Synthesis of 6-Aza-chromone Derivatives Through Cascade Carbonylation-Sonogashira-Cyclization
title_full_unstemmed One-pot Synthesis of 6-Aza-chromone Derivatives Through Cascade Carbonylation-Sonogashira-Cyclization
title_sort one-pot synthesis of 6-aza-chromone derivatives through cascade carbonylation-sonogashira-cyclization
publisher Nature Publishing Group
series Scientific Reports
issn 2045-2322
publishDate 2017-06-01
description Abstract We developed an efficient synthesis of aza-chromones from 3-iodo-4-(1H)-pyridones and terminal acetylenes via a cascade carbonylation-Sonogashira-cyclization reaction. By controlling the use of bases, both 6-aza-chromones 5 and 3-(4-oxo-1,4-dihydroquinoline-3-carbonyl)-4H-pyrano[3,2-c]quinolin-4-ones 6 could be selectively obtained in moderate to good yields.
url https://doi.org/10.1038/s41598-017-04693-7
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AT yingbeiqi onepotsynthesisof6azachromonederivativesthroughcascadecarbonylationsonogashiracyclization
AT xiaoqianzhou onepotsynthesisof6azachromonederivativesthroughcascadecarbonylationsonogashiracyclization
AT rongsheng onepotsynthesisof6azachromonederivativesthroughcascadecarbonylationsonogashiracyclization
AT yongzhouhu onepotsynthesisof6azachromonederivativesthroughcascadecarbonylationsonogashiracyclization
AT youhonghu onepotsynthesisof6azachromonederivativesthroughcascadecarbonylationsonogashiracyclization
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