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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
- Source :
- Scopus-Elsevier, ARKIVOC, Vol 2008, Iss 16, Pp 130-143 (2008)
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Abstract
- 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.
- Subjects :
- Tetrafluoroborate
Ionic bonding
4-pyrazolyl transfer
Pyrazole
Medicinal chemistry
lcsh:QD241-441
chemistry.chemical_compound
lcsh:Organic chemistry
Pyrazolo[3
Organic chemistry
4-c]isoquinoline
Isoquinoline
Acetonitrile
Benzamide
Pyrazolodibenzodiazocine
Pschorr reaction,pyrazolo(3,4-c)isoquinoline,pyrazolodibenzodiazocine,1,4-pyrazolyl transfer, X-ray structure
1,4-pyrazolyl transfer
Pschorr reaction
Pyrazolo[3,4-c]isoquinoline
X-ray structure
Organic Chemistry
Settore CHIM/08 - Chimica Farmaceutica
chemistry
Pschor reaction, pyrazolo[3,4-c]isoquinoline, pyrazolodibenzodiazocine, 1,4- pyrazolyl transfer, X-ray structure
Amine gas treating
Derivative (chemistry)
Subjects
Details
- Database :
- OpenAIRE
- Journal :
- Scopus-Elsevier, ARKIVOC, Vol 2008, Iss 16, Pp 130-143 (2008)
- Accession number :
- edsair.doi.dedup.....35563fc4daf5b185478e0f327899e478