Tandem Pd-catalyzed C-C coupling/recyclization of 2-(2-bromoaryl)cyclopropane-1,1-dicarboxylates with primary nitro alkanes

被引：20

作者：

Mikhaylov, Andrey A. ^{[1
]}

Dilman, Alexander D. ^{[1
]}

Novikov, Roman A. ^{[1
]}

Khoroshutina, Yulia A. ^{[1
]}

Struchkova, Marina I. ^{[1
]}

Arkhipov, Dmitry E. ^{[2
,3
]}

Nelyubina, Yulia V. ^{[2
]}

Tabolin, Andrey A. ^{[1
]}

Ioffe, Sema L. ^{[1
]}

机构：

[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Moscow 119991, Russia

[2] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 119991, Russia

[3] NI Pirogov Russian Natl Res Med Univ, Moscow 117997, Russia

来源：

TETRAHEDRON LETTERS | 2016年 / 57卷 / 01期

基金：

俄罗斯科学基金会;

关键词：

Palladium-catalysis; Cross-coupling reactions; Tandem reactions; Nitroalkanes; Donor-acceptor cyclopropanes; DONOR-ACCEPTOR CYCLOPROPANES; 1-ARYL-SUBSTITUTED NITROALKANES; MICHAEL ADDITION; REACTIVITY; CYCLOADDITIONS; CONSTRUCTION; 1,1-DIESTERS; ANNULATION; LEWIS; ARYLATION;

D O I：

10.1016/j.tetlet.2015.10.091

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first successful synthesis of 1H-2,3-benzoxazine 3-oxides has been described. The efficiency of the approach is provided by the C-C-coupling of 2-(2-bromoaryl)cyclopropane-1,1-dicarboxylates with primary nitroalkanes catalyzed by Pd(dba)(2)/JohnPhos system followed by in situ recyclization of the intermediates. Several representative transformations allowing selective modification of the nitronate as well as malonate functionalities in the resulting compounds are demonstrated. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：11 / 14

页数：4

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