Thiazole analogs of benzomorphans. III. Syntheses of 4,5,6,7,8,9-hexahydro-4,8-methano-5-methylthiazolo(4,5-c)azocine and 4,5,6,7,8,9-hexahydro-4,8-methano-5-methylthiazolo(5,4-c)azocine.

• 勝浦 公男

• 三橋 監物

抄録

Syntheses of 4, 5, 6, 7, 8, 9-hexahydro-4, 8-methano-5-methylthiazolo [4, 5-c] azocine (III) and 4, 5, 6, 7, 8, 9-hexahydro-4, 8-methano-5-methylthiazolo [5, 4-c] azocine (IV) are described. Thiazolization of 2-azabicyclo [3. 3. 1] nonan-8-one (V) gave the 2-aminothiazole (VII), which was converted into III by deamination, hydrolysis of the benzoyl group and Esch-weiler-Clarke N-methylation. The 2-hydroxyl derivative (XIII) was also synthesized. On the other hand, compound (IV) was synthesized by cyclization of the olefinic urethane (XXI) with phenylselenenyl chloride, as a key step. Deselenation of XXII with triphenyltin hydride followed by LiAlH₄ reduction gave IV. The urethane (XXI) was prepared from the 2-aminothiazole (XVIIa), which was obtained by condensation of the bromodiketone (XVI) and thiourea.

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 31 (6), 2094-2102, 1983

  公益社団法人 日本薬学会

キーワード

• 4, 5, 6, 7, 8, 9-hexahydro-4, 8-methano-5-methylthiazolo [5, 4-c] azocine

詳細情報

• CRID: 1390282679138219776
• NII論文ID: 130003769336
• DOI: 10.1248/cpb.31.2094
• ISSN: 13475223
• ISSN: 00092363
• Web Site: http://www.jstage.jst.go.jp/article/cpb1958/31/6/31_6_2094/_pdf
• 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