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

页码：8998 / 9011

页数：14

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