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Ring contraction synthesis of 2,5-disubstituted-3-arylamino-4-cyanopyrroles from 2,6-disubstituted-4-arylamino-5-cyanopyrimidines

✍ Scribed by Stefan Robev


Publisher
Elsevier Science
Year
1978
Tongue
French
Weight
209 KB
Volume
19
Category
Article
ISSN
0040-4039

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✦ Synopsis


A method for synthesis of 2,5-disubstituted-3-arylamino-4-cyanopyrroles from newly synthesised 2,6-disubstituted-4-arylamino-5-cyanopyrimidines by treatment with zinc and acetic acid, the yields being up to SO%, is developed.


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Treatment of 5-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione with primary arylamines in CH 2 Cl 2 at rt gave 5-[(arylamino)(cyano)methylene]-2,2-dimethyl-1,3-dioxane-4,6-diones in excellent yields. The latter compounds were utilized for the preparation of 2-cyano-4-quino