STRUCTURAL ELUCIDATION AND INDEPENDENT SYNTHESIS OF THE RADICAL-RADICAL COUPLING PRODUCTS OF 3-HYDROXYANTHRANILIC ACID WITH TYROSINE AND PHENOLS

被引:19
作者
MANTHEY, MK [1 ]
PYNE, SG [1 ]
TRUSCOTT, RJW [1 ]
机构
[1] UNIV WOLLONGONG, DEPT CHEM, POB 1144, WOLLONGONG, NSW 2500, AUSTRALIA
关键词
D O I
10.1021/jo00302a022
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The autoxidation of 3-hydroxyanthranilic acid (30HA) in the presence of tyrosine, p-cresol, or p-ethylphenol gives dibenzo[b,d]pyran-6-one products that arise from the coupling of the radical of 30HA with that derived from the substituted phenol. As a proof of the structure of these adducts, they have been independently synthesized by employing a palladium(0)-catalyzed coupling of appropriately functionalized aryl boronic acids with methyl 6-bromo-3-methoxy-2-nitrobenzoate. © 1990, American Chemical Society. All rights reserved.
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页码:4581 / 4585
页数:5
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