Decarboxylative C-S bond formation. Synthesis of 1,4-dimethyl-3,6-epidithio-2,5-piperazinedione and related compounds.
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Heating of dipotassium salt of 3, 6-dicarboxy-1, 4-dimethyl-2, 5-piperazinedione (4) with sulfur monochloride in dioxane gave 1, 4-dimethyl-3, 6-epidithio-2, 5-piperazinedione (11) in 33% yield with simultaneous decarboxylation. When the reaction mixture from 4 and S2Cl2 was reduced with NaBH4 and ethylated with ethyl iodide, cis 3, 6-bis (ethylthio) derivative (17) was obtained in 50% yield besides a trace amount of trans isomer (18) and the monoethylthio derivative (19). Reactions of other metal salts (16a, 16b, and 16c) with S2Cl2 did not improve the yield of 11. On the other hand the reaction of 4 with ethanesulfenyl chloride in dioxane did not yield 17, but gave 18, 19, and hydroxylated compounds (20, 21, and 22) in low yields. Similar results were obtained in the reaction of 4 with benzenesulfenyl chloride. The mechanism of the decarboxylative C-S bond formation was also discussed.
収録刊行物
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- CHEMICAL & PHARMACEUTICAL BULLETIN
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CHEMICAL & PHARMACEUTICAL BULLETIN 24 (2), 285-293, 1976
公益社団法人 日本薬学会
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詳細情報
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- CRID
- 1390001204172550784
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- NII論文ID
- 110003634996
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- NII書誌ID
- AA00602100
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- ISSN
- 13475223
- 00092363
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- 本文言語コード
- en
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- データソース種別
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- JaLC
- Crossref
- CiNii Articles
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- 抄録ライセンスフラグ
- 使用不可