Three-component microwave-assisted synthesis of 3,5-disubstituted pyrazolo[3,4-d]pyrimidin-4-ones
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. Unde...
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Royal Society of Chemistry
2022
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| Online Access: | http://eprints.sunway.edu.my/1979/ http://eprints.sunway.edu.my/1979/1/Three%20component%20microwave%20assisted%20synthesis.pdf |
| _version_ | 1848802172755509248 |
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| author | Ng, Jia Hui Tiekink, Edward R. T.* Dolzhenko, Anton V. |
| author_facet | Ng, Jia Hui Tiekink, Edward R. T.* Dolzhenko, Anton V. |
| author_sort | Ng, Jia Hui |
| building | SU Institutional Repository |
| collection | Online Access |
| description | 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 |
| first_indexed | 2025-11-14T21:19:08Z |
| format | Article |
| id | sunway-1979 |
| institution | Sunway University |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T21:19:08Z |
| publishDate | 2022 |
| publisher | Royal Society of Chemistry |
| recordtype | eprints |
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| spelling | sunway-19792022-04-13T02:16:20Z http://eprints.sunway.edu.my/1979/ Three-component microwave-assisted synthesis of 3,5-disubstituted pyrazolo[3,4-d]pyrimidin-4-ones Ng, Jia Hui Tiekink, Edward R. T.* Dolzhenko, Anton V. QD Chemistry 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 Royal Society of Chemistry 2022 Article PeerReviewed text en cc_by_4 http://eprints.sunway.edu.my/1979/1/Three%20component%20microwave%20assisted%20synthesis.pdf 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 http://doi.org/10.1039/D2RA00980C doi:10.1039/D2RA00980C |
| spellingShingle | QD Chemistry Ng, Jia Hui Tiekink, Edward R. T.* Dolzhenko, Anton V. Three-component microwave-assisted synthesis of 3,5-disubstituted pyrazolo[3,4-d]pyrimidin-4-ones |
| title | Three-component microwave-assisted synthesis of 3,5-disubstituted pyrazolo[3,4-d]pyrimidin-4-ones |
| title_full | Three-component microwave-assisted synthesis of 3,5-disubstituted pyrazolo[3,4-d]pyrimidin-4-ones |
| title_fullStr | Three-component microwave-assisted synthesis of 3,5-disubstituted pyrazolo[3,4-d]pyrimidin-4-ones |
| title_full_unstemmed | Three-component microwave-assisted synthesis of 3,5-disubstituted pyrazolo[3,4-d]pyrimidin-4-ones |
| title_short | Three-component microwave-assisted synthesis of 3,5-disubstituted pyrazolo[3,4-d]pyrimidin-4-ones |
| title_sort | three-component microwave-assisted synthesis of 3,5-disubstituted pyrazolo[3,4-d]pyrimidin-4-ones |
| topic | QD Chemistry |
| url | http://eprints.sunway.edu.my/1979/ http://eprints.sunway.edu.my/1979/ http://eprints.sunway.edu.my/1979/ http://eprints.sunway.edu.my/1979/1/Three%20component%20microwave%20assisted%20synthesis.pdf |