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
收藏
页码：9095 / 9100
页数：6
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