Reactions of 4-chloro-1-nitrobenzene with (3-chloro-4-methoxyphenyl)acetonitrile and (3,4-dimethoxyphenyl)acetonitrile; Synthesis of 8-chloro-1-methyl (and methylthiomethyl-6-(3,4-disubstituted phenyl)-4<i>H-s</i>-triazolo[4,3-<i>a</i>]-1,4-benzodiazepines

Vejdělek, Zdeněk; Holubek, Jiří; Buděšínský, Miloš; Ryska, Miroslav; Svátek, Emil; Protiva, Miroslav

doi:10.1135/cccc19880361

CCCC > Archive > 1988, Volume 53 > Issue 2 > p. 361

Reactions of 4-chloro-1-nitrobenzene with (3-chloro-4-methoxyphenyl)acetonitrile and (3,4-dimethoxyphenyl)acetonitrile; Synthesis of 8-chloro-1-methyl (and methylthiomethyl-6-(3,4-disubstituted phenyl)-4H-s-triazolo[4,3-a]-1,4-benzodiazepines

Zdeněk Vejdělek^a, Jiří Holubek^a, Miloš Buděšínský^b, Miroslav Ryska^a, Emil Svátek^a and Miroslav Protiva^a

^a Research Institute for Pharmacy and Biochemistry, 130 60 Prague 3
^b Institute of Organic Chemistry and Biochemistry Czechoslovak Academy of Sciences, 166 10 Prague 6

Abstract

Reactions of 4-chloro-1-nitrobenzene with (3-chloro-4-methoxyphenyl)acetonitrile and (3,4-dimethoxyphenyl)acetonitrile in methanolic potassium hydroxide gave the corresponding 3-aryl-5-chloro-2,1-benzisoxazoles Ia and Ib in good yields; compounds Va, Vb, VI-VIII and X were isolated as by-products and identified by means of spectra. Compounds Ia and Ib were transformed in five steps to the title compounds XVab and XVIab which were found inactive in tests for central depressant and anticonvulsant activity.

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Reactions of 4-chloro-1-nitrobenzene with (3-chloro-4-methoxyphenyl)acetonitrile and (3,4-dimethoxyphenyl)acetonitrile; Synthesis of 8-chloro-1-methyl (and methylthiomethyl-6-(3,4-disubstituted phenyl)-4H-s-triazolo[4,3-a]-1,4-benzodiazepines

Abstract