Development of Generation Method of Unstable Chemical Species Using Carbon Monoxide

利用一氧化碳生成不稳定化学物质的方法的开发

• 批准号: 10555317
• 负责人: SONODA Noboru
• 金额: $ 8.64万
• 依托单位: Kansai University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (B)
• 财政年份: 1998
• 资助国家: 日本
• 起止时间: 1998 至 1999
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-10555317/
• 关键词: Carbon Monoxide; Selenium; Selenium Carbon Monoxide; Indol; Quinazolinone; ニトロ化合物; ナイトレン

We investigated the new generation method of unstable chemical species by the use of the characteristics of carbon monoxide and the utilization of these unstable species in organic synthesis. In the course of this study, we found that nitre or nitrenoid species were generated smoothly by the reduction of aromatic nitro compounds with carbon monoxide in the presence of a catalytic amount of selenium. When 0-nitrostyrenes were treated with carbon monoxide in the presence of a catalytic amount of selenium, deoxyganation of nitro group followed by intramolecular cyclization proceeded efficiently to give the corresponding indols in moderate to good yields. On the reaction of 0-nitrobenzoylamides with carbon monoxide, 4(3H)-quinazolinones were synthesized in moderate to good yields. In addition, we have also developed the rhenium complexes having ligand of carbon monoxide acts as a catalyst on the Friedel-Craft alkylation of arenes with alkyl halides, Aldol type reaction of enol silyl ethers with carbonyl compounds and allylation of carbonyl compounds with allyic stannanes.

利用一氧化碳的特性，研究了不稳定化学物质的新生成方法，以及这些不稳定化学物质在有机合成中的应用。在本研究过程中，我们发现，在催化量的硒存在下，用一氧化碳还原芳香硝基化合物，可以顺利生成硝基或类硝基物质。在催化量的硒存在下，用一氧化碳处理0-硝基苯乙烯，硝基脱氧和分子内环化有效地得到相应的吲哚，收率中等至较高。以0-硝基苯甲酰酰胺为原料，与一氧化碳反应合成了4(3H)-喹唑啉酮类化合物。此外，我们还开发了以一氧化碳配体为催化剂的铼配合物，用于芳烃与卤代烃的Friedel-Craft烷基化反应，烯醇硅醚与羰基化合物的Aldol型反应以及羰基化合物与烯丙基锡烷的烯丙基化反应。

项目成果

Noboru Sonoda et al.: "Catalytic Use of Organostannyl Radical : The Reaction of 1, 2, 3-Selenadiazole with Olefins in the Presence of a Catalytic Amount of Tributyltin Hydride"Tetrahedron Letters. 40. 6293-9296 (1999)

Noboru Sonoda 等人：“有机锡烷基自由基的催化用途：在催化量的三丁基氢化锡存在下，1,2,3-硒二唑与烯烃的反应”四面体字母。

Noboru Sonoda et at.: "Reductive Coupling of Carbonyl Compounds Using Lanthanum Metal"Heteroatom Chemistry. 11(1). 81-85 (2000)

Noboru Sonoda 等人：“使用镧金属的羰基化合物的还原偶联”杂原子化学。

T. Nishino, Y. Nishiyama, and N. Sonoda: "Reductive Coupling of Carbonyl Compounds Using Lanthanum Metal"Heteroatom Chem.. 11(1). 81-85 (2000)

T. Nishino、Y. Nishiyama 和 N. Sonoda：“使用镧金属还原羰基化合物”杂原子化学.. 11(1)。

Noboru Sonoda et al.: "Synthesis of Indoles:Selenium-Catalyzed Reductive N-Heterocyclization of 2-Nitrostyrenes with Carbon Monoxide"Tetrahedron Letters. 40. 5717-5720 (1999)

Noboru Sonoda等人：“吲哚的合成：硒催化的2-硝基苯乙烯与一氧化碳的还原N-杂环化”四面体快报。

Noboru Sonoda et al.: "Synthesis of Indoles : Selenium-Catalyzed Reductive N-Heterocyclization of 2-Nitrostyrenes with Carbon Monoxide"Tetrahedron Letters. 40. 5717-5720 (1999)

Noboru Sonoda等人：“吲哚的合成：硒催化的2-硝基苯乙烯与一氧化碳的还原N-杂环化”四面体快报。