Synthetic Study of Heteroaromatic Amides as an Agricultural Drug...

农用杂芳酰胺的合成研究...

• 批准号: 01850194
• 负责人: SUZUKI Hitomi
• 金额: $ 1.98万
• 依托单位: KYOTO UNIVERSITY
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Developmental Scientific Research (B).
• 财政年份: 1989
• 资助国家: 日本
• 起止时间: 1989 至 1990
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-01850194/
• 关键词: Herbicide; Heteroaromatic Amides; Perfluoroalkyl Group; Three-Component Condensation; Growth-Inhibiting Activity; 農薬; 有機リチウム化合物; 合成; 有機ふつ素化合物; 藻類; ヘテロ環化合物

A variety of heteroaromatic amides having a general formula [1] Have been synthesized and their herbicidal activities examined.After extensive screening for paddy field herbicide, N-[alpha-(2-thienyl)-ethyl]-4-isopropylbenzamide [2] Was found to exhibit a high growth-inhibiting activity toward green and blue algae.A concise and economical four-step route to amide [2] has been developed starting from cumene and thiophene. A key step involves the direct three-component condensation of 4-isopropylbenzamide, thiophene and paraaldehyde in the presence of formic acid/phosphoric acid.A novel methodology for introducing perfluoroalkyl group directly into a variety of molecular frames has been developed and successfully employed to the synthesis of fluorine-containing heteroaromatic amides.

合成了多种具有通式[1]的杂芳酰胺并检测了它们的除草活性。经过对稻田除草剂的广泛筛选，发现N-[α-(2-噻吩基)-乙基]-4-异丙基苯甲酰胺[2]对绿藻和蓝藻表现出高生长抑制活性。一种简洁、经济的四步合成酰胺路线 [2]是从枯烯和噻吩开始开发的。关键步骤涉及4-异丙基苯甲酰胺、噻吩和多聚醛在甲酸/磷酸存在下的直接三组分缩合。开发了一种将全氟烷基直接引入到各种分子框架中的新方法，并成功应用于含氟杂芳酰胺的合成。

项目成果

H.Uno,T.Terakawa,H.Suzuki: "Boron TrifluorideーAssisted Alkylation of 2ーIsooxazolines.A Novel Route to NーUnsubstituted Isooxazolines" Chemistry Letters. 1079-1082 (1989)

H.Uno、T.Terakawa、H.Suzuki：“三氟化硼辅助的 2-异恶唑啉烷基化。N-未取代异恶唑啉的新路线”化学快报 1079-1082 (1989)。

H.Uno,Y.Matsushima,T.Tasaka,H.Suzuki: "A Convenient Synthesis of 4ー(Perfluoroalkyl)Pyrimidines and 4ー(Perfluoroalkyl)tetrahydropyrimidine" Bulletin of the Chemical Society of Japan. 63. 293-295 (1990)

H.Uno、Y.Matsushima、T.Tasaka、H.Suzuki：“4-(全氟烷基)嘧啶和 4-(全氟烷基)四氢嘧啶的便捷合成”日本化学会通报 63. 293-295 (1990)。 ）

H.Uno: "Boron Thifluorideーassisted Alkylation of 2ーIsooxazolines.A Novel Route to NーUnsubstituted Isooxazolidines" CHem.Lett.1079-1082 (1989)

H.Uno：“三氟化硼辅助的 2-异恶唑啉烷基化。N-未取代异恶唑烷的新路线”CHem.Lett.1079-1082 (1989)

H.Uno: "A Novel Route to 6ーPerfluoroalkyluracils" Synthesis. 381-382 (1989)

H.Uno：“合成 6-全氟烷基尿嘧啶的新途径”381-382 (1989)。

H.Uno.Okada,H.Suzuki: "A Novel Method for the Synthesis of田4ーHydrowyquinolines" Journal of Heterocyclic Chemistry. (1991)

H.Uno.Okada、H.Suzuki：“合成羟基喹啉的新方法”杂环化学杂志（1991）。