A New Domino Reaction under Microwave Irradiation for the Synthesis of Pyrazolo[5,1-b]quinazolinones

Jia Hui Ng; Felicia Phei Lin Lim; Edward R. T. Tiekink; Anton V. Dolzhenko

doi:10.1055/a-2075-3140

Synthesis, Table of Contents

Synthesis 2023; 55(17): 2691-2701
DOI: 10.1055/a-2075-3140

paper

A New Domino Reaction under Microwave Irradiation for the Synthesis of Pyrazolo[5,1-b]quinazolinones

Jia Hui Ng

^aSchool of Pharmacy, Monash University Malaysia, Jalan Lagoon Selatan, Bandar Sunway, Selangor Darul Ehsan 47500, Malaysia

,

Felicia Phei Lin Lim

^aSchool of Pharmacy, Monash University Malaysia, Jalan Lagoon Selatan, Bandar Sunway, Selangor Darul Ehsan 47500, Malaysia

,

Edward R. T. Tiekink

^bResearch Centre for Crystalline Materials, School of Medical and Life Sciences, Sunway University, 5 Jalan Universiti, Bandar Sunway, Selangor Darul Ehsan 47500, Malaysia

,

Anton V. Dolzhenko ∗

^aSchool of Pharmacy, Monash University Malaysia, Jalan Lagoon Selatan, Bandar Sunway, Selangor Darul Ehsan 47500, Malaysia

^cCurtin Medical School, Curtin Health Innovation Research Institute, Faculty of Health Sciences, Curtin University, GPO Box U1987 Perth, Western Australia 6845, Australia

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Abstract

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Abstract

Pyrazolo[5,1-b]quinazolinones were synthesized by consecutive pyrazole and quinazolinone ring closures in a new catalyst-free microwave-promoted domino reaction of hydrazine with 2-cyano-3-(methylthio)-3-(2-methoxycarbonylphenylamino)acrylates, which were prepared from methyl anthranilate and 2-cyano-3,3-bis(methylthio)acrylates. When 2-cyano-3,3-bis(methylthio)acrylates reacted directly with anthranilic acid hydrazide, the arylamino group remained intact, while the hydrazide moiety transformed into 1-acylpyrazoles and further to 2-(1,3,4-oxadiazolylidene)-2-cyanoacetates. The structures of representatives from each group of the prepared heterocyclic compounds were examined in detail by X-ray crystallography.

Key words

pyrazoles - quinazolines - domino reaction - oxadiazolines - anthranilates - microwave-assisted synthesis

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References

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