Benzoazepine-Fused Isoindolines via Intramolecular (3+2)-Cycloadditions of Azomethine Ylides with Dinitroarenes

被引：14
|
作者：
Wales, Steven M. [1 ]
Rivinoja, Daniel J. [1 ]
Gardiner, Michael G. [2 ]
Bird, Melissa J. [1 ]
Meyer, Adam G. [3 ]
Ryan, John H. [3 ]
Hyland, Christopher J. T. [1 ]
机构：
[1] Univ Wollongong, Sch Chem & Mol Biosci, Wollongong, NSW 2522, Australia
[2] Univ Tasmania, Sch Nat Sci Chem, Hobart, Tas 7001, Australia
[3] CSIRO Biomed Mfg, Ian Wark Lab, Bayview Ave, Clayton, Vic 3168, Australia
来源：
ORGANIC LETTERS | 2019年 / 21卷 / 12期
关键词：
1,3-DIPOLAR CYCLOADDITION; DIASTEREOSELECTIVE SYNTHESIS; FACILE DEAROMATIZATION; DECARBOXYLATIVE ROUTE; DERIVATIVES; SYSTEMS; BONDS;
D O I：
10.1021/acs.orglett.9b01580
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Aminobenzaldehydes bearing a pendant 3,5-dinitrophenyl group react thermally with N-substituted alpha-amino acids to form unprecedented benzoazepine-fused isoindolines. The reaction proceeds via a dearomatization/rearomatization sequence involving an intramolecular (3 + 2)-cycloaddition between the in situ formed azomethine ylide and the dinitroarene. Various glycine derivatives are tolerated as well as branched substrates based on cyclic, alpha-mono-, and alpha,alpha-disubstituted amino acids, giving single diastereomers in many cases. The method is scalable and gives products with a nitro group ready for further manipulation.
引用
收藏
页码：4703 / 4708
页数：6
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