Synthesis of Bicyclic Isoxazoles and Isoxazolines via Intramolecular Nitrile Oxide Cycloaddition

Wen-Chang Chen; Veerababurao Kavala; Yu-Hsuan Shih; Yu-Hsuan Wang; Chun-Wei Kuo; Tang-Hao Yang; Chia-Yu Huang; Hao-Hsiang Chiu; Ching-Fa Yao

doi:10.3390/molecules200610910

Synthesis of Bicyclic Isoxazoles and Isoxazolines via Intramolecular Nitrile Oxide Cycloaddition

Molecules. 2015 Jun 12;20(6):10910-27. doi: 10.3390/molecules200610910.

Authors

Wen-Chang Chen¹, Veerababurao Kavala², Yu-Hsuan Shih³, Yu-Hsuan Wang⁴, Chun-Wei Kuo⁵, Tang-Hao Yang⁶, Chia-Yu Huang⁷, Hao-Hsiang Chiu⁸, Ching-Fa Yao⁹

Affiliations

¹ Department of Chemistry, National Taiwan Normal University, 88, Sec. 4, Ting-Chow Road, Taipei 116, Taiwan. wcchen@taigenbiotech.com.
² Department of Chemistry, National Taiwan Normal University, 88, Sec. 4, Ting-Chow Road, Taipei 116, Taiwan. kavalaveeru@gmail.com.
³ Department of Chemistry, National Taiwan Normal University, 88, Sec. 4, Ting-Chow Road, Taipei 116, Taiwan. coshih@gmail.com.
⁴ Department of Chemistry, National Taiwan Normal University, 88, Sec. 4, Ting-Chow Road, Taipei 116, Taiwan. baby11710@hotmail.com.
⁵ Department of Chemistry, National Taiwan Normal University, 88, Sec. 4, Ting-Chow Road, Taipei 116, Taiwan. cwkuo.water@gmail.com.
⁶ Department of Chemistry, National Taiwan Normal University, 88, Sec. 4, Ting-Chow Road, Taipei 116, Taiwan. a129084303xx@gmail.com.
⁷ Department of Chemistry, National Taiwan Normal University, 88, Sec. 4, Ting-Chow Road, Taipei 116, Taiwan. tlotras@gmail.com.
⁸ Department of Chemistry, National Taiwan Normal University, 88, Sec. 4, Ting-Chow Road, Taipei 116, Taiwan. a210627@hotmail.com.
⁹ Department of Chemistry, National Taiwan Normal University, 88, Sec. 4, Ting-Chow Road, Taipei 116, Taiwan. cheyaocf@ntnu.edu.tw.

Abstract

An efficient and straight forward procedure for the syntheses of bicyclic isoxazole/isoxazoline derivatives from the corresponding dimethyl-2-(2-nitro-1-aryl/alkyl)-2-(prop-2-yn-1yl)malonates or dimethyl 2-allyl-2-(2-nitro-1-aryl/alkyl ethyl)malonate is described. High yields and simple operations are important features of this methodology.

Keywords: Yamaguchi reagent; bicyclic isoxazole/isoxazolines; cycloaddition; nitrile oxide; nitroalkane.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cycloaddition Reaction*
Isoxazoles / chemical synthesis*
Nitric Oxide / chemistry*

Substances

Isoxazoles
Nitric Oxide