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An Efficient One‐Pot Five‐Component Tandem Sequential Approach for the Synthesis of Pyranopyrazole Derivatives via Suzuki Coupling and Multicomponent Reaction
Author(s) -
Lu Zhangxiu,
Xiao Jinlong,
Wang Dongyang,
Li Yiqun
Publication year - 2015
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201500039
Subject(s) - chemistry , malononitrile , ethyl acetoacetate , hydrazine (antidepressant) , tandem , hydrate , suzuki reaction , component (thermodynamics) , melting point , proton nmr , fourier transform infrared spectroscopy , organic chemistry , combinatorial chemistry , catalysis , palladium , chemical engineering , chromatography , materials science , physics , engineering , composite material , thermodynamics
A one‐pot tandem sequential protocol for efficient synthesis of a series of new pyranopyrazole derivatives has been developed involving Suzuki coupling of 4‐bromobenzaldehyde and arylboronic acids followed by a four‐component reaction from readily available ethyl acetoacetate, malononitrile, and hydrazine hydrate. All of the products were fully characterized by melting point, FTIR, 1 H NMR, and 13 C NMR spectroscopy, and HRMS. The structure of one of the products was further established by X‐ray diffraction analysis. This method should provide a useful strategy for the construction of pyranopyrazole heterocycles.