Synthetic Study of Nitrogen-Containing Heterocyclic Compounds Using Molecular Transformation of Iminocyclobutenone

2015 Fiscal Year Final Research Report

• Project/Area Number: 25410114
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Synthetic chemistry
• Research Institution: Mie University
• Principal Investigator: Hachiya Iwao 三重大学, 工学(系)研究科(研究院), 准教授 (50312038)
• Project Period (FY): 2013-04-01 – 2016-03-31
• Keywords: イミン / シクロブテノン / 不斉還元 / β-ラクタム / キラルリン酸 / 共役付加 / 求核付加 / 含窒素化合物

Outline of Final Research Achievements

2-Aryl-4-quinolone synthesis was developed using the thermal rearrangement of iminocyclobutenones formed by a conjugate addition reaction of ketene silyl acetals to alkynyl imines. The 1,4- and 1,2-double nucleophilic addition reactions of ketene silyl acetals and trimethylsilyl cyanide to dialkynyl imines proceeded to give multi-substituted δ-lactam derivatives. Moreover, 1,4- and 1,6-double nucleophilic addition reactions of ketene silyl acetals to dialkynyl imines proceeded to give alkenyl iminocyclobutenones in good to high yields. Synthesis of a (±)-muscopyridine analogue was accomplished via the bicyclo-2-pyridone as a key intermediate, which was synthesized using ring-expansion reaction of the cyclic β-keto methyl ester with the alkynyl imine.

Free Research Field

有機合成化学