Non-classical transformation of benzendiazonium hydrogen sulfates. Access to 1,3-dimethylisochromeno[4,3-c]pyrazol-5(1H)-one, a potential benzodiazepine receptor ligand.
Molecules
; 18(10): 13096-110, 2013 Oct 22.
Article
em En
| MEDLINE
| ID: mdl-24152597
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.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Pirazóis
/
Ésteres do Ácido Sulfúrico
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Receptores de GABA-A
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GABAérgicos
/
Compostos de Diazônio
/
Isocumarinas
Idioma:
En
Revista:
Molecules
Assunto da revista:
BIOLOGIA
Ano de publicação:
2013
Tipo de documento:
Article
País de afiliação:
Itália