Development of a generation method for functionalized nitrile oxi | 7867
Drug Designing: Open Access

Drug Designing: Open Access
Open Access

ISSN: 2169-0138

+44 1223 790975

Development of a generation method for functionalized nitrile oxide

2nd International Conference and Expo on Drug Discovery & Designing

October 27-29, 2016 Rome, Italy

Nagatoshi Nishiwaki

Kochi University of Technology, Japan

Posters & Accepted Abstracts: Drug Des

Abstract :

Nitrile oxide is one of the useful synthetic tools for construction of heterocyclic compounds, which forms two bonds at the same time. Indeed, many researchers have energetically investigated for a long time, and published numerous papers. However, there are not so many reports with regard to functionalized nitrile oxides, which is presumably due to the poor availability of the precursors. During our study dealing with 4-nitroisoxazolin-5(2H)-one, we found nitrile oxide having a carbamoyl group 2 generated only upon treatment with water. When alkenes or alkynes are present in the reaction mixture, cycloaddition efficiently proceeded to afford isoxazolines or isoxazoles having a carbamoyl group. In the cycloaddition with nitriles, functionalized oxadiazoles were obtained. It is also possible to use 1, 3-dicarbonyl compounds as a dipolarophile, which leading to polyfunctionalized isoxazoles. Each cycloadduct has N-methylcarbamoyl group on the framework. We additionally investigated the chemical conversion of the carbamoyl group to other functional group. When N-methylcarbamoyl group is mesylated, it behaves like Weinreb amide to afford carboxylic acid, esters, amides, ketones and aldehyde upon treatment with water, alcohol, amines Grignard reagent, and DIBAL, respectively.

Biography :

Nagatoshi Nishiwaki has received his PhD from Osaka University in 1991. He has worked in Osaka Kyoiku University as an Assistant Professor (1991-2000) and then as Associate Professor (2001-2008). From 2000 to 2001, he has joined Professor Jorgensen’s group at Aarhus University, Denmark. From 2008 and 2009 he has worked at Anan National College of Technology as an Associate Professor. He then moved to Kochi University of Technology and became Professor in 2011. His research interests comprise synthetic organic chemistry using nitro compounds, heterocycles (ring transformations, 1, 3-dipolar cycloadditions, applications as tools in organic synthesis) and pseudo-intramolecular reactions.