Synthesis of pyrazolo[1,5- c ]quinazoline derivatives through the copper-catalyzed domino reaction of o -alkenyl aromatic isocyanides with diazo compounds

A novel copper-catalyzed domino reaction between o -alkenyl aromatic isocyanides and diazo compounds has been developed under mild reaction conditions. Various o -alkenyl aromatic isocyanides were prepared from readily available reactants. The reaction provides a general and efficient method for the...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2020-07, Vol.56 (55), p.7665-7668
Main Authors: Liu, Lu, Li, Lei, Mao, Shukuan, Wang, Xin, Zhou, Ming-Dong, Zhao, Yu-long, Wang, He
Format: Article
Language:English
Subjects:
Aromatic compounds
Cascade chemical reactions
Copper
Copper compounds
Crystallography
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Summary:A novel copper-catalyzed domino reaction between o -alkenyl aromatic isocyanides and diazo compounds has been developed under mild reaction conditions. Various o -alkenyl aromatic isocyanides were prepared from readily available reactants. The reaction provides a general and efficient method for the synthesis of pyrazolo[1,5- c ]quinazolines by the formation of two rings and three new bonds in a single step from readily available acyclic starting materials. A mechanism involving a tandem (3+2) cyclization/elimination/intramolecular aza-addition sequence was proposed.
ISSN:1359-7345
1364-548X
DOI:10.1039/d0cc00594k