Copper-mediated oxidative [3+2]-annulation of nitroalkenes and pyridinium ylides: general access to functionalized indolizines and efficient synthesis of 1-fluoroindolizines

被引：40
|
作者：
Motornov, Vladimir A. [1 ,2 ]
Tabolin, Andrey A. [1 ]
Nelyubina, Yulia V. [3 ]
Nenajdenko, Valentine G. [4 ]
Ioffe, Sema L. [1 ]
机构：
[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Leninsky Prosp 47, Moscow 119991, Russia
[2] DI Mendeleev Univ Chem Technol Russia, Higher Chem Coll, Miusskaya Sq 9, Moscow 125047, Russia
[3] Russian Acad Sci, AN Nesmeyanov Inst Organoelement Cpds, Vavilov Str 28, Moscow 119991, Russia
[4] Moscow MV Lomonosov State Univ, Dept Chem, Leninskie Gory 1, Moscow 119991, Russia
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2019年 / 17卷 / 06期
基金：
俄罗斯基础研究基金会;
关键词：
CALCIUM-CHANNEL ANTAGONIST; ONE-POT SYNTHESIS; 1,3-DIPOLAR CYCLOADDITION; REGIOSELECTIVE SYNTHESIS; AZOMETHINE YLIDES; SUBSTITUTED INDOLIZINES; ARYLBORONIC ACIDS; DERIVATIVES; ANNULATION; MECHANISM;
D O I：
10.1039/c8ob03126f
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A general method for the synthesis of substituted indolizines by copper(II) acetate-promoted oxidative [3 + 2]-annulation of alpha-fluoronitroalkenes with in situ generated pyridinium ylides was developed. Application of the copper(II) acetate-2,6-lutidine system provides efficient access to various 1-fluoroindolizines in up to 81% yield. Both electron-rich and electron-deficient nitroalkenes as well as different pyridinium and isoquinolinium salts can be involved in the reaction. Moreover, it was found that coppermediated annulation is applicable for other alpha-substituted (alkyl, chloro, and ester) nitroalkenes giving rise to the corresponding indolizines. First synthesis of monofluorinated [3,2,2]cyclazines was demonstrated via oxidative annulation of 3-unsubstituted fluoroindolizines with diethyl acetylene dicarboxylate.
引用
收藏
页码：1442 / 1454
页数：13
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