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Heterocyclization of 2,4‐disubstituted thiosemicarbazides with haloketones
Author(s) -
Tomita Yasuhiro,
Kabashima Shigeru,
Okawara Tadashi,
Yamasaki Tetsuo,
Furukawa Mitsuru
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.5570270343
Subject(s) - propiophenone , chemistry , butyrophenone , medicinal chemistry , ketone , stereochemistry , organic chemistry , haloperidol , neuroscience , dopamine , biology
2,4‐Disubstituted thiosemicarbazides were allowed to react with α ‐bromoacetophenone to give the anticipated 2,3‐dihydro‐6 H ‐1,3,4‐thiadiazines, whereas with β‐propiophenone and γ‐butyrophenone to afford the unexpected 2,3‐dihydro‐1,3,4‐thiadiazole. The reaction mechanism was also discussed.