Three-component microwave-assisted synthesis of 3,5-disubstituted pyrazolo[3,4-d]pyrimidin-4-ones

Ng, Jia Hui and Tiekink, Edward R. T.* and Dolzhenko, Anton V. (2022) Three-component microwave-assisted synthesis of 3,5-disubstituted pyrazolo[3,4-d]pyrimidin-4-ones. RSC Advances, 12 (14). pp. 8323-8332. ISSN 2046-2069

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A practical three-component method for the synthesis of pyrazolo[3,4-d]pyrimidin-4-ones was developed. The reaction was performed in a one-pot manner under controlled microwave irradiation using easily accessible methyl 5-aminopyrazole-4-carboxylates, trimethyl orthoformate, and primary amines. Under the optimized conditions, challenging substrates, such as N-1 unsubstituted 5-aminopyrazole-4-carboxylates with another substituted amino group in position 3, reacted selectively affording 5-substituted 3-arylamino-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-ones. The reaction tolerated a range of primary amines, including anilines. The advantages of the developed protocol include short reaction time, pot- and step-economy, and convenient chromatography-free product isolation. The structural features of representative products were explored by X-ray crystallography

Item Type: Article
Uncontrolled Keywords: Pyrazolo; anticancer target; 5-aminopyrazole-4-carboxylate;
Subjects: Q Science > QD Chemistry
Divisions: Others > Non Sunway Academics
Sunway University > School of Medical and Life Sciences [formerly School of Healthcare and Medical Sciences until 2020] > Sunway Biofunctional Molecules Discovery Centre [formerly Research Centre for Crystalline Materials until 2023]
Depositing User: Dr Janaki Sinnasamy
Related URLs:
Date Deposited: 13 Apr 2022 02:16
Last Modified: 13 Apr 2022 02:16

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