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

Autor:	Hirofumi Komiya, Yukio Oniyama, Yoshinori Tominaga, Yoshiki Matsuoka, Yoshimitsu Uchimura, Akira Hosomi, Shinya Kohra, Michiyo Hirayama
Rok vydání:	1990
Předmět:	chemistry.chemical_compound chemistry Bicyclic molecule Pyrimidine Organic Chemistry Oxide Organic chemistry Tetracyanoethylene Methylene Pyrazole Aliphatic compound Condensation reaction Medicinal chemistry
Zdroj:	Journal of Heterocyclic Chemistry. 27:647-660
ISSN:	1943-5193 0022-152X
DOI:	10.1002/jhet.5570270332
Popis:	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.
Databáze:	OpenAIRE
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