漆酶催化的儿茶酚与杂环1,3 -二羰基化合物之间的多米诺反应以及通过核磁共振光谱和X射线晶体结构分析对产物进行明确的结构解析。

The laccase-catalyzed domino reaction between catechols and heterocyclic 1,3-dicarbonyls and the unambiguous structure elucidation of the products by NMR spectroscopy and X-ray crystal structure analysis.

作者信息

Hajdok Szilvia, Conrad Jürgen, Leutbecher Heiko, Strobel Sabine, Schleid Thomas, Beifuss Uwe

机构信息

Bioorganische Chemie, Institut für Chemie, Universität Hohenheim, Garbenstrasse 30, D-70599 Stuttgart, Germany.

出版信息

J Org Chem. 2009 Oct 2;74(19):7230-7. doi: 10.1021/jo9011915.

DOI:10.1021/jo9011915

PMID:19739645

Abstract

The laccase-catalyzed reaction between catechols and heterocyclic 1,3-dicarbonyls (pyridinones, quinolinones, thiocoumarins) using aerial oxygen as the oxidant delivers benzofuropyridinones, benzofuroquinolinones, and thiocoumestans in a simple fashion, highly regioselectively with yields ranging from 55 to 98%. With barbituric acid derivatives the exclusive formation of dispiropyrimidinone derivatives takes place. The unambiguous and complete structure elucidation of all reaction products has been achieved by means of NMR spectroscopic methods (HSQMBC and band-selective HMBC) as well as by X-ray crystal structure analysis.

摘要

以空气中的氧气作为氧化剂，漆酶催化邻苯二酚与杂环1,3 - 二羰基化合物（吡啶酮、喹啉酮、硫代香豆素）之间的反应，能够以简单的方式高区域选择性地生成苯并呋喃吡啶酮、苯并呋喃喹啉酮和硫代库姆斯坦，产率在55%至98%之间。对于巴比妥酸衍生物，则专一性地生成二螺嘧啶酮衍生物。借助核磁共振光谱方法（HSQMBC和带选择性HMBC）以及X射线晶体结构分析，已实现对所有反应产物明确且完整的结构解析。