A Metal‐ and Azide‐free Oxidative Coupling Reaction for the Synthesis of Triazoloquinolines and their Application to Construct C−C and C‐P Bonds, 2‐Cyclopropylquinolines and Imidazoquinolines

An iodine‐promoted one‐pot cascade oxidative annulation reaction has been developed for the synthesis of [1,2,3]triazolo[1,5‐a]quinolines from methyl azaarenes and N‐tosylhydrazines. The reaction has a broad substrate scope and can be easily scaled up to gram‐scale. 1,2,3‐Triazoles are an important...

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Bibliographic Details
Published inAdvanced synthesis & catalysis Vol. 363; no. 2; pp. 490 - 496
Main Authors Zhi‐Hao Shang, Zhen‐Xiao Zhang, Wei‐Zhao Weng, Yu‐Fei Wang, Tian‐Wei Cheng, Qiu‐Yi Zhang, Li‐Qun Song, Tian‐Qi Shao, Kai‐Xuan Liu, Yan‐Ping Zhu
Format Journal Article
LanguageEnglish
Published Heidelberg Wiley Subscription Services, Inc 01.01.2021
Subjects
Chemical reactions
Chemical synthesis
Iodine
Organic compounds
Substrates
Triazoles
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Summary:An iodine‐promoted one‐pot cascade oxidative annulation reaction has been developed for the synthesis of [1,2,3]triazolo[1,5‐a]quinolines from methyl azaarenes and N‐tosylhydrazines. The reaction has a broad substrate scope and can be easily scaled up to gram‐scale. 1,2,3‐Triazoles are an important skeletal structure for the construction of C−C and C−P bonds, 2‐cyclopropylquinolines and imidazo[1,5‐a]quinolines, for which different synthetic applications were explored.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202001052