Synthesis of Boron-Containing Primary Amines

Molecules

Sheng-Hsuan Chung¹  Ting-Ju Lin¹  Qian-Yu Hu¹  Chia-Hua Tsai¹ 

[1] id="af1-molecules-18-12346">Department of Chemistry, Tamkang University, No. 151 Yingzhuan rd., Tamsui Dist., New Taipei City 25137, Taiw

关键词: boron;    multicomponent reactions;    Gabriel synthesis;    Ugi reaction;    peptoid;   

DOI  :  10.3390/molecules181012346

来源: mdpi

【 摘 要 】

In this study, boron-containing primary amines were synthesized for use as building blocks in the study of peptoids. In the first step, Gabriel synthesis conditions were modified to enable the construction of seven different aminomethylphenyl boronate esters in good to excellent yields. These compounds were further utilized to build peptoid analogs via an Ugi four-component reaction (Ugi-4CR) under microwave irradiation. The prepared Ugi-4CR boronate esters were then successfully converted to the corresponding boronic acids. Finally, the peptoid structures were successfully modified by cross-coupling to aryl/heteroaryl chlorides via a palladium-mediated Suzuki coupling reaction to yield the corresponding derivatives in moderate to good yields.

【 授权许可】

CC BY   
© 2013 by the authors; licensee MDPI, Basel, Switzerland.