Synthetic Studies on the Biologically Active 3-Benzazepines

生物活性3-苯并氮杂类化合物的合成研究

• 批准号: 63571013
• 负责人: IKEDA Masazumi
• 金额: $ 1.41万
• 依托单位: Kyoto Pharmaceutical University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for General Scientific Research (C)
• 财政年份: 1988
• 资助国家: 日本
• 起止时间: 1988 至 1989
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-63571013/
• 关键词: 2-Phenethylamine; 3-Benzazepine; 3-Benzazepin-2-one; Sulfoxide; Pummerer reaction; X-Ray analysis; Cephalotaxine; 2-フェネチルアミン; 3-ベンズアゼピン; 3-ベンズアゼピン-2-オン; X-線結晶解析

1. A series of (methylsulfinyl)acetamides reacted with electron-rich arenes in the presence of p-toluenesulfonic acid to give alpha-(methylthio)aryl- acetamides, some of which were transformed into biologically active aryl- ethylamines such as (<plus-minus>)-macromerin2.1,3,4,5-Tetrahydro-2H-3-benzazepin-2-one derivatives were synthesized by an acid-catalyzed cyclization of N-(2-arylethyl)-N-methyl-2-sulfinylacet- amides. Some chemical transformations of the 2H-3-benzazepin-2-ones were also investigated.3. Synthesis of 1,3,5,6,9,15-hexahydro-4H-1,3-dioxolo[4,5-h]pyrrolo[2,1-b]- [3]benzazepin-2(1H),8-dione, a key intermediate for the total synthesis of (<plus-minus>)-cephalotaxine, has been achieved in a stereoselective manner by a synthetic sequence involving an acid-catalyzed cylization of the alpha- sulfinylacetamide as a key ste

1. 在对甲苯磺酸的存在下，一系列（甲基亚砜基）乙酰胺与富电子芳烃反应生成α -（甲基硫）芳基乙酰胺，其中一些通过酸催化环化N-（2-芳基乙基）-N-甲基-2-亚砜基乙酰胺合成了具有生物活性的芳基乙胺，如（<正负b>）-macromerin2.1,3,4,5-四氢- 2h -3-苯甲平-2- 1衍生物。研究了2h -3-苯并氮平-2-酮的一些化学转化。以酸催化-亚砜酰乙酰胺环化为关键步骤，以立体选择性方式合成了1,3,5,6,9,15-六氢- 4h -1,3-二唑啉[4,5-h]吡咯[2,1-b]- [3]benzazepin-2(1H)，8-二酮，这是（<正- >）-头孢噻嗪全合成的关键中间体

项目成果

石橋弘行: "A Convenient Synthesis of 1,3,4,5-Tetrahydro-2H-3-benz-azepin-2-ones by Acid-Catalyzed Cyclization of N-(2-Arylethy1)-N-methy1-2-sulfinylacetamides" Chem.Pharm.Bull.37. 939-943 (1989)

Hiroyuki Ishibashi：“通过 N-(2-芳基 1)-N-甲基 1-2-亚磺酰基乙酰胺的酸催化环化方便合成 1,3,4,5-四氢-2H-3-苯并氮杂卓-2-酮” Chem.Pharm.Bull.37. 939-943 (1989)

石橋弘行: "A Convenient Synthesis of 1,3,4,5-Tetrahydro-2H-3-benz-azepin-2-ones by Acid-Catalyzed Cyclization of N-(2-Arylethyl)-N-methyl-2-sulfinylacetamides" Chem.Pharm.Bull.37. 939-943 (1989)

Hiroyuki Ishibashi：“通过 N-(2-芳乙基)-N-甲基-2-亚磺酰基乙酰胺的酸催化环化方便合成 1,3,4,5-四氢-2H-3-苯并氮杂平-2-酮” Chem.Pharm.Bull.37. 939-943 (1989)

Hiroyuki Ishibashi: "A Convenient Synthesis of 1, 3, 4, 5-Tetrahydro-2H-3-benzazepin-2-ones by Acid-Catalyzed Cyclization of N-(2-Arylethyl)-N-methyl-2-sulfinylacetamides" Chem. Pharm. Bull., 37, 939-943 (1989).

Hiroyuki Ishibashi：“通过 N-(2-芳乙基)-N-甲基-2-亚磺酰乙酰胺的酸催化环化方便合成 1, 3, 4, 5-四氢-2H-3-苯并氮杂卓-2-酮” Chem

石橋弘行: "A Formal Total Synthesis of (±)-Cephalotaxine" J.Chem.Soc.Chem.Commun.

Hiroyuki Ishibashi：“(±)-三尖杉酯碱的正式全合成”J.Chem.Soc.Chem.Commun。

Hiroyuki Ishibashi: "A New, Convenient Route to Erbstatin and N-Acetyl-1, 2-didehydrodopamine" Chem Pharm. Bull., 37, 2214-2216 (1989).

Hiroyuki Ishibashi：“一种新的、便捷的厄布他汀和 N-乙酰基-1, 2-二脱氢多巴胺途径” Chem Pharm。