Crystallization-induced amide bond formation creates a boron-centered spirocyclic system

Heterocyclic communications

article

Brighid B. Pappin¹  Stephan M. Levonis¹  Peter C. Healy²  Milton J. Kiefel³  Michela I. Simone⁴  Todd A. Houston³ 

[1] Institute for Glycomics, Griffith University;School of Natural Sciences, Griffith University;Institute for Glycomics and School of Natural Sciences, Griffith University;Priority Research Centre for Chemical Biology and Clinical Pharmacology, University of Newcastle

关键词: amidation;    boronate ester;    crystal structure;    dative bond;    Lewis acid;   

DOI  :  10.1515/hc-2017-0023

学科分类：内科医学

来源: De Gruyter

【 摘 要 】

The 5-nitrosalicylate ester of 2-acetamidophenylboronic acid (C 15 H 10 BN 2 O 6 ) is formed under crystallization conditions from the 5-nitrosalicylate ester of 2-aminophenylboronic acid. The boron at the center of this structure exists as a tetrahedral complex produced by a dative bond with the amide carbonyl. The perpendicular shape produces an unusual packing structure including a bifurcated hydrogen bond between the amide hydrogen and carbonyl groups on two neighboring molecules. We propose that this reaction occurs due to increased Lewis acidity of the nitrosalicylate ester of 2-aminophenylboronic acid.

【 授权许可】

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