A core switching strategy to pyrrolo[2,3-b]quinolines and diazocino[1,2-a]indolinones

被引：7
|
作者：
Jones, Alan M. [1 ,2 ]
Patterson, Stephen [1 ]
Lorion, Magali M. [1 ]
Slawin, Alexandra M. Z. [1 ]
Westwood, Nicholas J. [1 ]
机构：
[1] Univ St Andrews, Sch Chem & Biomed Sci Res Complex, St Andrews KY16 9ST, Fife, Scotland
[2] Manchester Metropolitan Univ, Div Chem & Environm Sci, John Dalton Bldg, Manchester M1 5GD, Lancs, England
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2016年 / 14卷 / 38期
基金：
英国工程与自然科学研究理事会; 英国生物技术与生命科学研究理事会;
关键词：
DIVERSITY-ORIENTED SYNTHESIS; SMALL-MOLECULE TOOL; SODIUM DICHLOROISOCYANURATE; OXIDATIVE CLEAVAGE; ORGANIC-SYNTHESIS; REARRANGEMENT; 1,2,3,4-TETRAHYDRO-9(10H)-ACRIDINONE; DERIVATIVES; INHIBITOR; HYPOCHLORITE;
D O I：
10.1039/c6ob01566b
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Two novel core-switching rearrangements to natural product-like privileged scaffolds that proceed in up to 99% yield have been developed. The deviation away from planarity of the central N-acyl urea carbonyl, caused by the structure of the medium-sized ring, dictates the exclusive reaction outcome. Proposed mechanisms and products for the reaction pathways are supported by small molecule X-ray crystallography and an isolated intermediate. Twenty-four novel rearrangement products are reported.
引用
收藏
页码：8998 / 9011
页数：14
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