Zhao-Jie Liu

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.

SYNTHESIS OF O,O-DIPHENYL [SUBSTITUTED (2-SELENOMORPHOLIN-4-YL-ACETYL AMINO)] ALKYL PHOSPHONATES

A series of O,O-diphenyl [substituted (2-selenomorpholin-4-yl-acetyl amino)] alkyl phosphonates were synthesized by the reactions of selenomorpholine with O,O-diphenyl 2-chloro- acetylamino alkyl phosphonates. The structures of all new compounds have been confirmed by 1 H NMR, 31 P NMR, IR spectroscopy, Mass spectroscopy and elemental analyses.

Synthesis and Properties of Novel Imidazolone Derivatives Containing a Sulfur Atom

Novel 5-(2-chlorophenylmethylidene)-2-thio-4-imidazolinones 3 and 2-Alkythio-5-(2-chlorophenylmethylidene)-4H-imidazolin-4-ones 4 have been synthesized via a tandem aza-Wittig reaction to develop more imidazolinones that may possess biological activities. The target compounds were identified by GC-MS, IR, and 1H NMR spectroscopies, and element analysis, and, in the case of 4k , its structure was established by single crystal X-ray diffraction. They showed not only fungicidal activities against Gibberella zeae, Cercospora beticola, Fusarium oxysporium, Rhizoctonia solani, and Botryosphaeria berengeriana, but also growth inhibition of Barnyard grass and Cole root and stalk.

A FACILE SYNTHESIS OF 6-ALKOXYL (AROXYL)-1,5-DIHYDROPYRAZOLO-[3,4-d]PYRIMIDIN-4-ONE DERIVATIVES

Reaction of 3-methylthio-l-phenyl-5-{[( triphenyl-X-phosphanylidene)methane] -amino} -lH-pyrazole-4-carboxylic acid ethyl ester with ROH in the presence of RONa or passium carbonate affords 6-alkoxyl/aroxy 1-3-alkylthio-1,5-diphenyl-1,5-dihydropyrazolo[3,4-d]pyrimidin -4-one

5-Anilino-3-benzyl­sulfanyl-6-(3-chloro­anilino)-1-phenyl-1H-pyrazolo­[3,4-d]pyrimidin-4(5H)-one

In the title compound, C30H23ClN6OS, the benzyl, the 3-chloroanilino, the phenyl and the anilino groups form dihedral angles of 85.95u2005(6), 29.63u2005(7), 28.55u2005(1) and 87.48u2005(6)°, respectively, with the pyrazolo[3,4-d]pyrimidine unit [maximum deviation = 0.052u2005(2)u2005Å]. An intramolecular N—H⋯N hydrogen bond occurs. The crystal structure features N—H⋯O hydrogen bonds.

Ethyl {4-[5-(3-methyl­phen­yl)-3-methyl­sulfanyl-4-oxo-1-phenyl­pyrazolo[3,4-d]pyrimidin-6-yl­oxy]phen­oxy}acetate

The title compound, C29H26N4O5S, is based on an almost planar pyrazolo[3,4-d]pyrimidin-4-one core. Molxadecules are packed through weak interxadmolecular C—H⋯O and C—H⋯N interxadactions.

Bis(4‐formyl‐3‐methyl‐1‐phenyl‐1H‐pyrazol‐5‐yl) sulfide

The molxadecule of the title compound, C22H18N4O2S, is non-planar and possesses no crystallographic symmetry. The crystal structure involves intermolecular C—H⋯O hydrogen bonds.