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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
Author(s) -
Tominaga Yoshinori,
Matsuoka Yoshiki,
Oniyama Yukio,
Uchimura Yoshimitsu,
Komiya Hirofumi,
Hirayama Michiyo,
Kohra Shinya,
Hosomi Akira
Publication year - 1990
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570270332
Subject(s) - chemistry , methylene , guanidine , medicinal chemistry , tetracyanoethylene , condensation , pyrimidine , stereochemistry , organic chemistry , physics , thermodynamics
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.