776298-90-9

Upstream product

• 103-71-9 phenyl isocyanate 
• 750598-28-8 C₃₁H₂₈N₃O₂PS 
• 40745-03-7 5-amino-3-methylsulfanyl-1-phenyl-1H-pyrazole-4-carboxylic acid ethyl ester 

Downstream Products

• 1047642-99-8 5-amino-3-methylthio-1-phenyl-6-phenylamino-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one 
• 776298-91-0 3-methylsulfanyl-1-phenyl-5-(N'-phenyl-N''-propyl-guanidino)-1H-pyrazole-4-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

Synthesis of 3-methylthio-1-phenyl-pyrazolo[3,4-d][1,2,4]triazolo[1,5-a]pyrimidin-4-one derivatives via tandem aza-Wittig reaction

An efficient and convenient procedure for the synthesis of 3-methylthio-1-phenyl-pyrazolo[3,4-d][1,2,4]triazolo[1,5-a]pyrimidin-4-one derivatives (4a–m) via tandem aza-Wittig and annulation reactions with iminophosphoranes 1, aryl isocyanate, and substitu

Synthesis of some novel 5-substituted benzamido-6-arylamino-pyrazolo[3,4-D]pyrimidin-4-one derivatives for herbicidal activity

Sixteen novel 3-methylthio-5-substituted benzamido-6-arylamino-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4 (5H)-one derivatives (4a–p) were successfully synthesized from iminophosphoranes, aryl isocyanate, and substituted benzoylhydrazine. The structures of the title compounds were elucidated by FT-IR, 1H NMR, 13C NMR, and HRMS. Herbicidal activity of the compounds 4a–p against Brassica napus (rape), Echinochloa crusgalli (barnyard grass), Cucumis sativus (cucumber), and Triticum aestivum (wheat) were determined. The results showed that 5-(2-chlorobenzamido)-6-phenylamino-3-methylthio-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4 (5H)-one (4c) displayed remarkable inhibition activity against the stalk and root of rape with 100% inhibition rate at the dosages of 10 mg/L and 100 mg/L, and 5-(4-nitrobenzamido)-6-phenylamino-3-methylthio-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4 (5H) -one (4d) exhibited excellent activity against the stalk and root of barnyard grass with 100% inhibition rate at the same dosages.

Regioselective synthesis and bioactivity of new 5-amino-6- Arylamino-pyrazolo[3,4-d]-pyrimidin-4(5H)-one derivatives

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

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.

Synthesis and herbicidal activity of novel pyrazolo[3,4-d]pyrimidin-4-one derivatives containing aryloxyphenoxypropionate moieties

The 6-(4-alkoxycarbonylalkoxy)phenoxy-3-alkylthio(alkylsulfonyl)-1-phenyl-5-(substituted phenyl)pyrazolo[3,4-d]pyrimidin-4-ones 6 and 7 have been synthesized via the tandem aza-Wittig and annulation reactions of the corresponding iminophosphoranes 4, arom

Versatile synthesis and fungicidal activities of 6-amino-3-alkylthio-1,5- dihydro-1-phenyl-pyrazolo [3,4-d]pyrimidin-4-one derivatives

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.