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

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 dipolarophile...

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Bibliographic Details
Published inTetrahedron Vol. 71; no. 48; pp. 9095 - 9100
Main Authors Albota, Florin, Drăghici, Constantin, Caira, Mino R., Dumitrascu, Florea
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 02.12.2015
Elsevier
Subjects
1,3-Dipolar cycloaddition
Bis(1,3-dipoles)
Chemistry
Chemistry, Organic
Physical Sciences
Pyrrolo[2,1-a]isoquinoline
Pyrrolo[2,1-a]phthalazine
Science & Technology
Sydnone-N-ylides
1,3-Dipolar cycloaddition
Pyrrolo[2,1-a]isoquinoline
Pyrrolo[2,1-a]phthalazine
Bis(1,3-dipoles)
Sydnone-N-ylides
ALKENES
ONE-POT SYNTHESIS
EFFICIENT SYNTHESIS
DERIVATIVES
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Summary: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. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2015.10.021