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

页码：4703 / 4708

页数：6

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