Efficient Synthesis of Quinazolines from Aryl Imidates and N‐Alkoxyamide by Ir(III)‐Catalyzed C−H Amidation/Cyclization

An Ir(III) catalyst was used for the first time to realize the synthesis of quinazolines by C−H bond activation/cyclization with N‐alkoxyamides as amidation reagents. This reaction has the advantages of wide substrate adaptability, good to excellent yields under mild conditions, short reaction times...

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Bibliographic Details
Published in:European journal of organic chemistry 2021-08, Vol.2021 (29), p.4144-4147
Main Authors: Fan, Wei‐Tai, Huang, Zhibin, Xu, Xu, Tu, Guangliang, Geng, Jingyao, Ji, Shun‐Jun, Zhao, Yingsheng
Format: Article
Language:English
Subjects:
Bioactive compounds
Cyclization
C−H activation
Hydrogen bonds
Inert atmospheres
Ir(III)-catalyzed
Quinazolines
Reagents
Substrates
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Summary:An Ir(III) catalyst was used for the first time to realize the synthesis of quinazolines by C−H bond activation/cyclization with N‐alkoxyamides as amidation reagents. This reaction has the advantages of wide substrate adaptability, good to excellent yields under mild conditions, short reaction times, and no need for an inert atmosphere. Importantly, several quinazolines from bioactive compounds were obtained, which highlights the importance of this new method. We developed an unprecedented iridium‐catalyzed C−H activation/cyclization to synthesize isoquinoline compounds efficiently using ethyl benzimidate and N‐alkoxyamides. This reaction has the advantages of wide substrate adaptability, short reaction times and no need for an inert atmosphere. In addition, some drug molecules smoothly converted into aminating reagents, reacted efficiently and afforded molecules with potential drug activity.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202100726