6533b824fe1ef96bd1280003
RESEARCH PRODUCT
Comparative studies of the Pschorr reaction in the pyrazole series. Access to the new dibenzo[e,g]pyrazolo[1,5-a][1,3]diazocine system of pharmaceutical interest
Maria Antonietta SabatinoFiorella MeneghettiGabriella BombieriSalvatore PlesciaBenedetta MaggioDemetrio RaffaStella CascioferroMaria Valeria RaimondiGiuseppe Daidonesubject
Tetrafluoroborate1Ionic bonding4-pyrazolyl transferPyrazoleMedicinal chemistrylcsh:QD241-441chemistry.chemical_compoundlcsh:Organic chemistryPyrazolo[3Organic chemistry4-c]isoquinolineIsoquinolineAcetonitrileBenzamidePyrazolodibenzodiazocinePschorr reactionpyrazolo(34-c)isoquinolinepyrazolodibenzodiazocine14-pyrazolyl transfer X-ray structure14-pyrazolyl transfer; Pschorr reaction; Pyrazolodibenzodiazocine; Pyrazolo[34-c]isoquinoline; X-ray structureOrganic ChemistryPschorr reactionSettore CHIM/08 - Chimica FarmaceuticachemistryPschor reaction pyrazolo[34-c]isoquinoline pyrazolodibenzodiazocine 14- pyrazolyl transfer X-ray structureAmine gas treatingX-ray structureDerivative (chemistry)description
The diazonium tetrafluoroborate 11 obtained from 2-amino-N-methyl-N-(1-phenyl-3- methylpyrazol-5-yl)benzamide was transformed in dry acetonitrile via an ionic or radical pathway. Differences were observed with respect to ionic or radical transformations in aqueous media of the analogous diazonium hydrogen sulfate 1 derived from the same amine. In acetonitrile solution, the ionic pathway was characterized by an increased yield of 1,4-dimethyl- 3-phenyl-pyrazolo(3,4-c)isoquinolin-5-one 4 and by the formation of its isomer, the new derivative 7,9-dimethyldibenzo(e,g)pyrazolo(1,5-a)(1,3)diazocin-10(9H)-one 12. When the reaction followed a radical pathway, the pyrazolo(3,4-c)isoquinoline derivative 4 and N-methyl- 2-(1-phenyl-3-methylpyrazol-5-yl)benzamide 17, the latter due to a 1,4-pyrazolyl transfer process, were isolated in low yields. Decomposition of the solid diazonium tetrafluoroborate at its melting point gave compounds 4, 12 and the N-(1-phenyl-3-methylpyrazol-5-yl)-2- fluorobenzamide 17. The crystal structure of compound 12 was also determined.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2008-01-01 |