Synthesis of new substituted pyrazolo[1,5-a]-pyrimidines and pyrazolo[1,5-a]1,3,5-triazines |
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| Affiliation: | 1. School of Pharmacy, China Medical University, No. 91 Hsueh-Shih Rd., Taichung 40402, Taiwan, ROC;2. The Ph.D. Program for Cancer Biology and Drug Discovery, China Medical University, No. 91 Hsueh-Shih Rd., Taichung 40402, Taiwan, ROC;3. Department of Environmental Science, Nihon Pharmaceutical University, 10281 Komuro, Ina-machi, Kitaadachi-gun, Saitama, Japan;1. College of Chemistry, Chemical Engineering and Materials Science, Collaborative Innovation Center of Functionalized Probes for Chemical Imaging in Universities of Shandong, Key Laboratory of Molecular and Nano Probes, Ministry of Education, Shandong Provincial Key Laboratory of Clean Production of Fine Chemicals, Shandong Normal University, Jinan 250014, PR China;2. Center for Intelligent Chemical Instrumentation, Department of Chemistry and Biochemistry, Ohio University, Athens, OH 45701, United States;1. National Medicines Institute, 00-725 Warsaw, Poland;2. Institute of Nuclear Chemistry and Technology, 03-195 Warsaw, Poland;1. Department of Chemistry, R. K. Mission Vivekananda Centenary College, Rahara, Kolkata 700 118, West Bengal, India;2. Chemistry Division, CSIR-Indian Institute of Chemical Biology, Jadavpur 700 032, West Bengal, India;3. Department of Chemistry, The University of Reading, PO Box 224, Whiteknights, Reading RG6 6AD, UK |
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| Abstract: | 5-Substituted 3-amino-1H-pyrazole-4-carbonitriles 2a-d react with appropriate biselectrophilic reagents in the presence of (TEA) to give the substitution products pyrazolo[1,5-a]pyrimidines 4a-d, 6a-d and pyrazolo[1,5-a ]1,3,5-triazines 8a-d. Compounds 6a and 8a react with secondary amines to 10a-c and 11a-c. Treatment of 2a with malonodinitrile results in the substituted pyrazolo-[1,5-a]pyrimidine 16. Condensation of 2a, 2c and 2d with ethyli-dene-malodintriles leads to racemic dihydro-pyrazolo[1,5-a] pyr-imidines 18a-e. Reaction of diene 20 with the heterodienophile 21 leads to formation of Diels-Alder adduct 22. |
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