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Polarized ethylenes. IV. Synthesis of polarized ethylenes using thioamides and methyl dithiocarboxylates and their application to syntheses of pyrazoles, pyrimidines, pyrazolo[3,4‐ d ]pyrimidines, and 5‐aza[2.2.3]cyclazines

1990; Wiley; Volume: 27; Issue: 3 Linguagem: Inglês

10.1002/jhet.5570270332

1943-5193

Yoshinori Tominaga, Yoshiki Matsuoka, Yukio Oniyama, Yoshimitsu Uchimura, Hirofumi Komiya, Michiyo Hirayama, Shinya Kohra, Akíra Hosomi,

Synthesis and Reactivity of Sulfur-Containing Compounds

Abstract 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.