Development of the efficient synthetic method for heterocycles utilized by isocyanide and conjugated 1,3-dipolar

2019 Fiscal Year Final Research Report

• Project/Area Number: 17K05778
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Organic chemistry
• Research Institution: Kanazawa University
• Principal Investigator: Soeta Takahiro 金沢大学, 物質化学系, 准教授 (10506819)
• Project Period (FY): 2017-04-01 – 2020-03-31
• Keywords: イソシアニド / イソシアニドジハライド / 複素環

Outline of Final Research Achievements

Multifunctionalized oxazoles and pyrroles are important building blocks in organic synthesis as well as in pharmaceuticals, natural products, and functional materials. In this study, a novel synthetic method for multifunctional oxazole and pyrrole derivatives has been achieved. We focused on the utility of isocyanide dichloride, which is a stable and readily available chemical species via addition of chlorine onto isocyanides. The presence of the two halogen atoms activates the C=N double bond toward nucleophiles, which realizes nucleophilic additions in a sequential manner. We initially examined whether isocyanide dichloride which was easily prepared from the corresponding TosMIC with SO2Cl2, could synthesize oxazole and pyrrole derivatives.

Free Research Field

有機合成化学

Academic Significance and Societal Importance of the Research Achievements

環境への負荷の低減や資源問題などの観点から，産業界では有機合成化学において高効率的 なワンポット合成や多成分反応への志向が高まっている。また，化合物の望みの位置に置換基を 導入する際には，多段階を要し，基質にも制限が出てしまうことが従来の問題点であった。本研 究のイソシアニドを用いる反応では潜在的に2つの結合をワンポットで生成することができる ため，環境に優しく高効率的な有機合成反応開発へ広く展開可能となることから，本研究は非常 に意義深いものである。