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Synthesis of boron-containing primary amines.

ABSTRACT: 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.

SUBMITTER: Chung SH

PROVIDER: S-EPMC6269827 | biostudies-other | 2013

REPOSITORIES: biostudies-other

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Synthesis of boron-containing primary amines.

Chung Sheng-Hsuan SH Lin Ting-Ju TJ Hu Qian-Yu QY Tsai Chia-Hua CH Pan Po-Shen PS

Molecules (Basel, Switzerland) 20131008 10

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 th ...[more]

PMID: 24108399

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