Unexpected synthesis by a non-classical Pschorr reaction of 3,5-dimethyl-1-phenyl-1,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one, with binding affinity for the central benzodiazepine receptor

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Abstract

The reaction of the diazonium salt 12 derived from N-(2-aminophenyl)-N,3-dimethyl-1-phenyl-1H-pyrazole-5-carboxamide with copper sulfate and sodium chloride in the presence of ascorbic acid afforded the unexpected products 3,5-dimethyl-1-phenyl-1,5-dihydro-4H-pyrazolo[4,3-c]¬quinolin-4-one (17) and N-methyl-2-(3-methyl-1-phenyl-1H-pyrazol-5-yl)aniline (19), accompanied by N-(2-chlorophenyl)-N,3-dimethyl-1-phenyl-1H-pyrazole-5-carboxamide (18). Products 17 and 19 are formed via a non-classical Pschorr reaction. The formation of 17 represents an alternative to the literature synthesis of this biologically active compound. The molecular structure of 18 was confirmed by single-crystal X-ray analysis.
Lingua originaleEnglish
pagine (da-a)80-90
Numero di pagine11
RivistaArkivoc
Volume2014
Stato di pubblicazionePublished - 2014

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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