Development of novel synthetic reactions based on mutual cooperation of nitrogen-oxygen bonds and multiple bonds

2016 Fiscal Year Final Research Report

• Project/Area Number: 26460024
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Chemical pharmacy
• Research Institution: Osaka City University (2016); Kobe Pharmaceutical University (2014-2015)
• Principal Investigator: MIYATA Okiko 大阪市立大学, 大学院理学研究科, 客員教授 (90102110)
• Co-Investigator(Renkei-kenkyūsha): UEDA Masafumi 神戸薬科大学, 薬学部, 准教授 (00340935) ; MIYOSHI Tetsuya 神戸薬科大学, 薬学部, 助教 (10549992)
• Project Period (FY): 2014-04-01 – 2017-03-31
• Keywords: アルコキシアミン / アルコキシアアミド / オキシムエーテル / 極性転換反応 / ベンゾフラン / インドール / イソキサゾール / ケトン

Outline of Final Research Achievements

Aiming to the development of useful methods for the synthesis of biologically active compounds, we have developed new synthetic reactions in which functional groups and multiple bonds mutually cooperate. Alkoxyamines, alkoxyamides, and oxime ethers having nitrogen and oxygen bonds were selected as substrates in this study. As a result, various new carbon-carbon forming reactions featured by the polarity inversion of carbonyl functionality and unprecedented cascade reactions were developed. Treatment of N-alkoxyenamines with triarylaluminum reagents afforded alfa-arylcarbonyls. Alkoxyamides with an alkenyl or alkynyl group underwent cyclization-rearrangement reaction to give isoxazole derivatives. Oxime ethers enabled to be converted to substituted benzofuropyrroles by triethylborane-mediated radical addition-rearrangement-cyclization-lactamization. Under the same conditions, hydrazones were transformed to indoleacetic acid derivatives.

Free Research Field

医歯薬学