The cyclization of 5‐amino‐3‐methylthiopyrazole‐4‐carbonitriles or 4‐carboxamides 3a‐j, which were prepared by the reaction of ketene dithioacetals 1a,b [1a: bis(methylthiomethylenemalononitrile; 1b: bis(methylthio)methylenecyanoacetamide] with hydrazines (hydrazine hydrate, phenylhydrazine, p‐chlorophenylhydrazine, p‐nitrophenylhydrazine), with formamide or carbon disulfide proceeded to give the corresponding 4‐amino‐ or 4‐hydroxy‐3‐methylthiopyrazolo[3,4‐d]pyrimidines 6a‐h in good yields. 3‐Aminopyrazolo[3,4‐d]pyrimidine derivatives 6i‐1 were also obtained by the application of the cyclization reaction of 3,5‐diaminopyrazoles with formamide.
The synthesis of dinaphtho[1,2‐b:2′,3′‐d]thiophene (6), dinaphtho[2,1‐b:2′,3′‐d]thiophene (15), dinaphtho‐[1,2‐b:1′,2′‐d]thiophene (20), dinaphtho[2,1‐b:1′,2′‐d]thiophene (26), dinaphtho[2,3‐b:2′,3′‐d]thiophene (37) and dinaphtho[1,2‐b:2′,1′‐d]thiophene (45) has been accomplished.
Polarized ethylenes having both electron‐donating (an amino or a methylthio group) and electron‐accepting (cyano, carbamoyl, methyl ester) groups on the adjacent two olefinic carbon atoms were prepared by the condensation of S‐alkylthioamidinium salts or methyl dithiocarboxylates with the corresponding active methylene compounds in good yields. These polarized ethylenes were alternatively synthesized by the reaction of thioamides or methyl dithiocarboxylates with tetracyanoethylene oxide in good yields. Reactions of these polarized ethylenes with hydrazine or guanidine derivatives occurred smoothly to give the corresponding pyrazole and pyrimidine derivatives in good yields. The synthesis of 5‐aza[2.2.3]cyclazine derivatives using polarized ethylenes is also described.
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