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DOI: 10.1055/a-2075-3140
A New Domino Reaction under Microwave Irradiation for the Synthesis of Pyrazolo[5,1-b]quinazolinones
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.
Key words
pyrazoles - quinazolines - domino reaction - oxadiazolines - anthranilates - microwave-assisted synthesisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2075-3140.
- 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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