Abstract
The compound 2-((1,3-dimethyl-1H-pyrazol-5-yl)(methyl)carbamoyl)benzene-diazonium hydrogen sulfate (10) was reacted with copper sulfate and sodium chloride, in the presence of ascorbic acid as reducing agent, to afford a mixture of the chlorinated epimers 4′-chloro-2,2′,5′-trimethyl-2′,4′-dihydrospiro[isoindoline-1,3′-pyrazol]-3-one (18) and (19), the epimers 4′-hydroxy-2,2′,5′-trimethyl-2′,4′-dihydrospiro[isoindoline-1,3′-pyrazol]-3-one (20) and (21), and N-(1,3-dimethyl-1H-pyrazol-5-yl)benzamide (22). Under the foregoing conditions, diazonium salt 10 affords neither the 2-chloro-N-(1,3-dimethyl-1H-pyrazol-5-yl)-N-methylbenzamide (23) nor the tricyclic derivative 24, the classical products of the Sandmeyer and Pschorr reactions, respectively. Finally, by heating 20 at 210 °C the compound 1,3-dimethylisochromeno[4,3-c]pyrazol-5(1H)-one (24) was obtained. The transformation under the above conditions of 2-((4-chloro-3-methyl-1-phenyl-1H-pyrazol-5-yl)(methyl)carbamoyl)benzendiazonium hydrogen sulphate (11) afforded 4′,4′-dichloro-2,5′-dimethyl-2′-phenyl-2′,4′-dihydrospiro[isoindoline-1,3′-pyrazol]-3-one (29) as the sole reaction product.
Lingua originale | English |
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pagine (da-a) | 13096-13110 |
Numero di pagine | 15 |
Rivista | Molecules |
Volume | 18 |
Stato di pubblicazione | Published - 2013 |
All Science Journal Classification (ASJC) codes
- ???subjectarea.asjc.2700.2700???
- ???subjectarea.asjc.1600.1602???
- ???subjectarea.asjc.1600.1601???
- ???subjectarea.asjc.1300.1313???
- ???subjectarea.asjc.3000.3003???
- ???subjectarea.asjc.3000.3002???
- ???subjectarea.asjc.1600.1606???
- ???subjectarea.asjc.1600.1605???