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Search for "N-ylide" in Full Text gives 6 result(s) in Beilstein Journal of Organic Chemistry.
Sydnone C-4 heteroarylation with an indolizine ring via Chichibabin indolizine synthesis
Beilstein J. Org. Chem. 2016, 12, 2503–2510, doi:10.3762/bjoc.12.245
- ; Chichibabin synthesis; indolizine; pyridinium N-ylide; sydnone; Introduction In recent decades, interest in the syntheses of biheteroaryls has been focused on the creation of new hetaryl–hetaryl C(sp2)–C(sp2) bonds, in particular through cross-coupling reactions. These reactions are catalyzed by palladium or
- products 12a–c with yields in the range of 41–52%. Bearing in mind that the formation of indolizines through Chichibabin synthesis and 1,3-dipolar cycloaddition reaction requires in both cases the formation of an intermediate pyridinium N-ylide, it is expected that in these cycloadditions a mixture of
Unusual reactions of diazocarbonyl compounds with α,β-unsaturated δ-amino esters: Rh(II)-catalyzed Wolff rearrangement and oxidative cleavage of N–H-insertion products
Beilstein J. Org. Chem. 2016, 12, 1904–1910, doi:10.3762/bjoc.12.180
- appearance of the amides 4 and 7 during the processes studied (Scheme 3). At first, upon catalytic decomposition of diazocarbonyl compounds 2a–c and 3c, N-ylide E is generated, stabilization of which by proton transfer produces an ordinary N–H-insertion product, α-ketoamine F. Similar reactions are well
Indolizines and pyrrolo[1,2-c]pyrimidines decorated with a pyrimidine and a pyridine unit respectively
Beilstein J. Org. Chem. 2015, 11, 1079–1088, doi:10.3762/bjoc.11.121
- structures of two of the starting materials, 4-(2-pyridyl)pyrimidine and 4-(4-pyridyl)pyrimidine, are also reported. Keywords: indolizine; nitrogen heterocycles; N-ylide; 4-pyridylpyrimidine; pyrrolo[1,2-c]pyrimidine; Introduction Two heteroarenes linked through a single bond [1] proved to be versatile
- 17 on the oxirane ring in the 1,2-epoxybutane (Scheme 4). The reactive intermediate obtained by the ring opening of the 1,2-epoxybutane abstracts a methylene proton from the salt, generating the corresponding N-ylide (18) in situ. The N-ylide reacts further with the acetylenic dipolarophile to give a
New highlights of the syntheses of pyrrolo[1,2-a]quinoxalin-4-ones
Beilstein J. Org. Chem. 2014, 10, 2377–2387, doi:10.3762/bjoc.10.248
- opening and generation of the benzimidazolium N-ylide 7 by the action of the alkoxide. The benzimidazolium N-ylide 7 reacts with the activated alkynes 3 to give the corresponding primary cycloadduct dihydropyrrolo[1,2-a]benzimidazoles 8. The formation of pyrrolo[1,2-a]quinoxalin-4-ones 4 involves the
Isoxazolium N-ylides and 1-oxa-5-azahexa-1,3,5-trienes on the way from isoxazoles to 2H-1,3-oxazines
Beilstein J. Org. Chem. 2014, 10, 1896–1905, doi:10.3762/bjoc.10.197
- diazo esters B involved an isoxazolium N-ylide intermediate C formed by an attack of the rhodium carbenoid onto the isoxazole nitrogen. Furthermore, ylide C could undergo either a 1,2-shift to directly generate oxazine E or a ring opening to 1-oxa-5-azahexa-1,3,5-triene D, followed by a 6π
Synthesis and ring openings of cinnamate-derived N-unfunctionalised aziridines
Beilstein J. Org. Chem. 2012, 8, 1747–1752, doi:10.3762/bjoc.8.199
- Alan Armstrong Alexandra Ferguson Department of Chemistry, Imperial College London, South Kensington, London, SW7 2AZ, U.K. 10.3762/bjoc.8.199 Abstract tert-Butyl cinnamates are aziridinated with high trans-selectivity by an N–N ylide generated in situ from N-methylmorpholine and O
- carbonyl compounds. Our method produces trans-NH-aziridines from α,β-unsaturated carbonyl compounds in good to excellent yield with high diastereoselectivity (Figure 1) [21]. An N–N ylide (aminimine) is the presumed active intermediate, formed from the reaction of a tertiary amine promoter and an aminating
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