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
a   School of Pharmacy, Monash University Malaysia, Jalan Lagoon Selatan, Bandar Sunway, Selangor Darul Ehsan 47500, Malaysia
,
Felicia Phei Lin Lim
a   School of Pharmacy, Monash University Malaysia, Jalan Lagoon Selatan, Bandar Sunway, Selangor Darul Ehsan 47500, Malaysia
,
Edward R. T. Tiekink
b   Research Centre for Crystalline Materials, School of Medical and Life Sciences, Sunway University, 5 Jalan Universiti, Bandar Sunway, Selangor Darul Ehsan 47500, Malaysia
,
a   School of Pharmacy, Monash University Malaysia, Jalan Lagoon Selatan, Bandar Sunway, Selangor Darul Ehsan 47500, Malaysia
c   Curtin Medical School, Curtin Health Innovation Research Institute, Faculty of Health Sciences, Curtin University, GPO Box U1987 Perth, Western Australia 6845, Australia
› Author Affiliations
This work is supported by the Ministry of Higher Education, Malaysia under the Fundamental Research Grant Scheme (Grant no. FRGS/1/2020/STG04/MUSM/02/2). Sunway University Sdn Bhd is thanked for financial support of the X-ray crystallographic study (Grant no. GRTIN-RRO-56-2022).


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.

Supporting Information



Publication History

Received: 22 February 2023

Accepted after revision: 17 April 2023

Accepted Manuscript online:
17 April 2023

Article published online:
11 May 2023

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