Preparation of Sydnone Compounds Substituted by Thio and Seleno Functional Groups at the 4-Positions
| Autor: | Tsutomu Nonaka, Ching-Sy Chen, Mou-Yung Yen, Toshio Fuchigami, Hsien-Ju Tien |
|---|---|
| Rok vydání: | 1986 |
| Předmět: | |
| Zdroj: | Bulletin of the Chemical Society of Japan. 59:487-491 |
| ISSN: | 1348-0634 0009-2673 |
| DOI: | 10.1246/bcsj.59.487 |
| Popis: | The introduction of thio and seleno functional groups to the 4-position of a sydnone ring was successfully attempted using 4-lithiosydnones (2) and 4-bromosydnones (3) as starting compounds. The reaction of 2 with tetraalkylthiuram disulfides, bis[alkoxy(thiocarbonyl)] disulfides, and bis[alkylthio(thiocarbonyl)] disulfides provided 4-sydnonyl dithiocarbamates, O-alkyl S-(4-sydnonyl) dithiocarbonates, and dialkyl 4-sydnonyl trithiocarbonates, respectively in good yields. In addition, treatment of 2 with thiocyanogen and selenocyanogen gave rise to bis(4-sydnonyl) sulfides (11) and bis(4-sydnonyl) selenides (12), respectively. These products, 11 and 12 were also formed by the reaction of 3 with potassium thiocyanate and selenocyanate, respectively. Furthermore, it was found that 3 reacted with selenourea and potassium O-ethyl dithiocarbonate under heating to provide 12 and 11, respectively. It was also found that the reactivity of these sydnone compounds 2 and 3 was quite different in many cases from that ... |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|