Studies of heterocyclic compounds. VI. The reactions of 5,6-dihydrothiazolo(2,3-b)thiazolium salts with O- and S-nucleophiles.

• 大塚 宏子

• 宮坂 貞

• 荒川 基一

抄録

The reaction of 5, 6-dihydrothiazolo [2, 3-b] thiazolium salts (1) with hydroxide ion furnished disulfide of 3-(2-mercaptoethyl)-4-thiazolin-2-one (6). The reaction of 1 with hydrogensulfide ion furnished 3-(2-mercaptoethyl)-4-thiazolin-2-thione (7) and/or its disulfide (8) and with N, N-dimethyldithiocarbamate ion furnished 3-(N, N-dimethyl-dithiocarbamylethyl)-4-thiazolin-2-thione (12) whereas the reaction of 1b with thiophenolate ion afforded 3-(2-phenylthioethyl)-4-thiazolin-2-thione (18b), thiazole (21), 6b, phenyl 2-[2-(4-phenylthiazolin-2-thion-3-yl) ethylthio] ethyl disulfide (22) and phenyl 2-phenylthioethyl disulfide (23). Brief reaction mechanism of the formation of these products are discussed. The reaction of 1 is considered to be initiated by the attack of the nucleophile on the polarized >C=N< bond to form an adduct and to proceed through AE-mechanism. The elimination stage of the reaction is concluded to depend upon basicity, polarizability and other properties of the reagent to induce either the cleavage of S₇-C_7a bond, the cleavage of S₇-C_7a and N-C₅ bonds, or another attack of the reagent on C₅ or on S₇.

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 23 (12), 3243-3253, 1975

  公益社団法人 日本薬学会

キーワード

• Drug Discovery
• General Chemistry
• General Medicine

詳細情報

• CRID: 1390282679150860032
• NII論文ID: 110003621836
• NII書誌ID: AA00602100
• DOI: 10.1248/cpb.23.3243
• ISSN: 13475223
• ISSN: 00092363
• Web Site: http://www.jstage.jst.go.jp/article/cpb1958/23/12/23_12_3243/_pdf
• Web Site: https://search.jamas.or.jp/link/ui/1976106776
• 本文言語コード: en
• データソース種別:
  • JaLC
  • Crossref
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可