1027575-17-2Relevant academic research and scientific papers
A new regioselective synthesis and bioactivity of 1H-pyrazolo[3,4-d] pyrimidin-4(5H)-one derivatives
Wang, Hong-Qing,Liu, Zhao-Jie,Yang, Li-Min,Ding, Ming-Wu
, p. 393 - 397 (2004)
A series of new 1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one Derivatives 5 has been designed and regio-selectively synthesized via a tandem aza-Wittig reaction. The structures of all compounds prepared have been confirmed by 1H NMR, IR, EI-MS spectros
Regioselective synthesis and bioactivity of new 5-amino-6- Arylamino-pyrazolo[3,4-d]-pyrimidin-4(5H)-one derivatives
Wang, Hong-Qing,Zhou, Wei-Ping,Wang, Yu-Yuan,Lin, Can-Rong,Liu, Zhao-Jie
experimental part, p. 256 - 260 (2009/06/21)
A novel approach to regioselective synthesis of new 5-amino-6-arylamino-1H- pyrazolo[3,4-d]pyrimi- din-4(5H)-one 5 derivatives via a tandem aza-wittig and annulation reaction of iminophosphorance 2, aromatic isocyanates and hydrazine in 69.6-94.7% isolated yields is reported. The compound 5 reacted with triethyl orthoformate to give compound 6 in good yield (65.8-82.8%). Their structure was clearly confirmed by spectroscopy data (IR, 1H NMR, MS, elemental analysis) and the results of preliminary bioassay indicated that compounds 5 and 6 possess high antifungal activity against Botrytis cinerea Pers and Sclerotinia sclerotiorum, and compound 5h showed 100, 96.4, and 90.2% inhibitory rate to Botrytis cinerea Pers, Pyricularia oryzae, and Sclerotinia sclerotiorum at the concentration of 50 mg/L. The antifungal activities of compound 6 were generally higher than those of compound 5.
Synthesis and antifungal activities of novel 5-amino-6-arylamino-1H- pyrazolo[3,4-d]pyrimidin-4(5H)-one derivatives
Wang, Hong-Qing,Zhou, Wei-Pimg,Wang, Y.U.-Yuan,Lin, Can-Rong
experimental part, p. 7321 - 7325 (2010/05/18)
A novel approach was developed to regioselectively synthesize new 5-amino-6-arylamino-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one 5 derivatives via a tandem aza-Wittig and annulation reactions of iminophosphorane 2, aromatic isocyanates, and hydrazine in 52-92% isolated yields. The compounds 5 reacted with triethyl orthoformate to give 1,8-2H-pyrazolo[3,4-d][1,2,4]triazolo[1,5-a] pyrimidin-4-ones 6 in good yields (62-94%). Their structures were clearly confirmed by spectroscopy data (IR, 1H NMR, MS), elemental analysis, or X-ray diffraction crystallography. The results of preliminary bioassay indicated that the compounds 5 and 6 possessed high antifungal activity against Botrytis cinerea Pers and Sclerotinia sclerotiorum. Compounds 5 showed much better antifungal activities when R was Me instead of PhCH2. Especially, compounds 6c, 6g, and 6i inhibited Sclerotinia by 100% at the concentration of 50 mg/L and by 83, 83, and 82% at the dosage of 10 mg/L, respectively.
Versatile synthesis and fungicidal activities of 6-amino-3-alkylthio-1,5- dihydro-1-phenyl-pyrazolo [3,4-d]pyrimidin-4-one derivatives
Wang, Hong-Qing,Liu, Zhao-Jie,Ding, Ming-Wu
, p. 2039 - 2050 (2007/10/03)
A series of new 6-alkylamino-3-alkylthio-1-phenyl-1H-pyrazolo[3,4-d] pyrimidin-4(5H)-one derivatives 5 and 6 have been rapidly synthesized by a novel solution-phase regioselective synthetic method. Treatment of pyrazole o-aminoester 1 with dibromotriphenylphosphorane gave iminophosphorane 2, which underwent a aza-Wittig reaction with phenyl ioscyanate to provide the carbodiimide 3. The latter intermediate reacted with alkylamines and regioselectively provided the 1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one derivatives 5 and 6, some of which exhibited good fungicidal activity.
