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Reactions of 4-(Dicyanomethylene)-3-methyl-1-phenyl-2-pyrazolin-5-one Towards Amines and Phenols

✍ Scribed by Metwally, Saoud A. M. ;El Naggar, Galal M. ;Younis, Mansour I. ;El-Emary, Talaat I. ;Elnagdi, Mohamed Hilmy

Publisher
John Wiley and Sons
Year
1989
Tongue
English
Weight
416 KB
Volume
1989
Category
Article
ISSN
0947-3440

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✦ Synopsis

R 80 Ph f C6H4CH3-(2) c C,jH,CH3-(4) h d C,H40CH3-(2) i 1037 -HCN 7 R C,H40H-(4) C, H, NH, -(4) ' ? J C d N H R t CpH4N02-(4) C6H4CI-(2) I Key Word: 2-Pyrazolin-5-one derivatives e attack of the amine at the cyclic amide carbonyl function should afford 6 by ring opening and recyclization. Alternately, attack at C-a of the dicyanomethylene moiety would afford 7 which then loses hydrogen cyanide yielding the arylaminocyanomethylene derivative 8. Ph C, H, OCH, -(4) 8a -2

Cyclic 1,2-diones and 1,2,3-triones readily condense with malononitrile to yield the dicyanomethylene derivatives 1 and Z2-'). Whereas 1 reacts with nucleophilic reagents (e.g. carbanions of active methylene compounds to yield products resulting from initial attack of the nucleophile at C-p with respect to cyano functlons5', compounds 2 react with nucleophiles (e.g. aromatic amines) to yield products of initial attack by the nucleophile at C-cc to the cyano functions ','I.

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