Unusual Pericyclic Reactivity of 4-Nitrobenzofuroxans in 1,3-Dipolar Cycloaddition with N-Benzyl Azomethine Ylide - A New Example of Multiple C-C-Bond Forming Transformations

被引：3

作者：

Starosotnikov, Alexey M. ^{[1
]}

Bastrakov, Maxim A. ^{[1
]}

Kachala, Vadim V. ^{[1
]}

Fedyanin, Ivan, V ^{[2
]}

Shevelev, Svyatoslav A. ^{[1
]}

Dalinger, Igor L. ^{[1
]}

机构：

[1] ND Zelinsky Inst Organ Chem RAS, Leninsky Prosp 47, Moscow 119991, Russia

[2] AN Nesmeyanov Inst Organoelement Cpds RAS, Vavilova Str 28, Moscow 119991, Russia

来源：

CHEMISTRYSELECT | 2018年 / 3卷 / 34期

基金：

俄罗斯科学基金会;

关键词：

azomethine ylides; benzofuroxans; 1,3-dipolar cycloaddition; polycycles; pyrrolidines; NITROGEN-OXYGEN SYSTEMS; DIELS-ALDER REACTIVITY; NITRIC-OXIDE DONORS; NUCLEOPHILIC-SUBSTITUTION; POLYCYCLIC HETEROSYSTEMS; NITROARENES; DEAROMATIZATION; NITROFUROXANS; DERIVATIVES; DESIGN;

D O I：

10.1002/slct.201802117

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A series of 4-nitrobenzofuroxans were examined in [3 + 2]cycloaddition reactions with N-benzyl azomethine ylide. The reaction outcome was found to be dependent on the nature of substituent 7-R: for R = H and SR' the products of double cycloaddition of the dipole were isolated, whereas for R = CH3, OR' and NR'R '' tetrahydroisoindoles annelated with furoxan ring were the sole products. As a result efficient chemoselective method for the synthesis of mono- and bis-pyrrolidine fused benzofuroxan derivatives was developed.

引用

页码：9773 / 9777

页数：5

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