Synthesis of 3, 6-Diethoxycarbonyl-3, 6-epidithia-1, 4-dimethyl-2, 5-piperazinedione and Related Compounds. Formation of C-S Bond by the Reaction of Carbanion and Sulfur Monochloride
Hino, T; Sato, T
| HERO ID | 4933272 |
|---|---|
| In Press | No |
| Year | 1974 |
| Title | Synthesis of 3, 6-Diethoxycarbonyl-3, 6-epidithia-1, 4-dimethyl-2, 5-piperazinedione and Related Compounds. Formation of C-S Bond by the Reaction of Carbanion and Sulfur Monochloride |
| Authors | Hino, T; Sato, T |
| Journal | Chemical and Pharmaceutical Bulletin |
| Volume | 22 |
| Issue | 12 (1974) |
| Page Numbers | 2866 |
| Abstract | Reaction of 3, 6-diethoxycarbonyl-1, 4-dimethyl-2, 5-piperazinedione (15), prepared by heating of diethyl methylaminomalonate (14), with NaH in dioxane and followed treatment with S2Cl2 gave 3, 6-epidithio- and 3, 6-epitetrathio-3, 6-diethoxycarbonyl-1, 4-dimethyl-2, 5-piperazinediones (16b and 16d), which have the skeletone (1) observed in fungal metabolites such as sporidesmin. The reduction of 16 with NaBH4 in methanol gave the dethio derivative (15) in good yield. The reaction of 16d with triphenylphosphine in tetrahydrofurane gave 16c and 16b. The reaction of diethyl malonate derivatives (23a, b, and c) with NaH and S2Cl2 in dioxane gave the corresponding disulfides or trisulfides (24a, b, and c). Some reactions of proline anhydride (5) and sarcosine anhydride (7) with S2Cl2 or sulfur were examined. |
| Url | http://www.jstage.jst.go.jp/article/cpb1958/22/12/22_12_2866/_article |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |