1,3-Dipolar cycloaddition between acetylenic dipolarophiles and sydnone-N-ylides as bis(1,3-dipoles)

被引：13

作者：

Albota, Florin ^{[1
]}

Draghici, Constantin ^{[1
]}

Caira, Mino R. ^{[2
]}

Dumitrascu, Florea ^{[1
]}

机构：

[1] Roumanian Acad, Ctr Organ Chem CD Nenitzescu, Bucharest 060023, Romania

[2] Univ Cape Town, Dept Chem, ZA-7701 Rondebosch, South Africa

来源：

TETRAHEDRON | 2015年 / 71卷 / 48期

关键词：

Sydnone-N-ylides; Bis(1,3-dipoles); 1,3-Dipolar cycloaddition; Pyrrolo[2,1-a]phthalazine; Pyrrolo[2,1-a]isoquinoline; ONE-POT SYNTHESIS; EFFICIENT SYNTHESIS; DERIVATIVES; ALKENES;

D O I：

10.1016/j.tet.2015.10.021

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1,3-Dipolar cycloaddition reaction of sydnone-N-ylides, as model bis(1,3-dipoles), with acetylenic dipolarophiles in 1,2-epoxybutane under reflux gave exclusively pyrroloazines containing a sydnone moiety that resulted by preferred reaction of the N-ylide 1,3-dipole with the acetylenic dipolarophiles. The assembled sydnone-ylide hybrid structures were generated in situ from N-heteroaromatic bromides. The structure of the new compounds was assigned by IR and NMR spectroscopy and confirmed by X-ray analysis for a representative compound. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：9095 / 9100

页数：6

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