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Search for "ethynylation" in Full Text gives 6 result(s) in Beilstein Journal of Organic Chemistry.
N-Sulfenylsuccinimide/phthalimide: an alternative sulfenylating reagent in organic transformations
Beilstein J. Org. Chem. 2023, 19, 1471–1502, doi:10.3762/bjoc.19.106
- Morita–Baylis–Hillman carbonates from isatins by using a Lewis base catalytic system (Scheme 52) [84]. Screening several organocatalysts showed that the 1,3-oxo-ethynylation of starting materials with silylethynyl-1,2-benziodoxol-3(1H)-ones 123 was obtained by using catalyst N, while 1,3
Effect of uridine protecting groups on the diastereoselectivity of uridine-derived aldehyde 5’-alkynylation
Beilstein J. Org. Chem. 2017, 13, 1533–1541, doi:10.3762/bjoc.13.153
- reagent, we manage to obtain an excellent diastereoselectivity. Indeed, by using the most bulky 2’,3’-O-TIPS protecting groups and TIPS-ethynylmagnesium bromide, the 5’-ethynylation was achieved in a 99:1 ratio in favor of the 5’S-isomer. The resulting building block with a broad potential in nucleos(t
Synthesis of spiro[isoindole-1,5’-isoxazolidin]-3(2H)-ones as potential inhibitors of the MDM2-p53 interaction
Beilstein J. Org. Chem. 2016, 12, 2793–2807, doi:10.3762/bjoc.12.278
- -ethynylbenzamides 1. The latter are easily accessible through ethynylation of N-substituted 2-iodobenzamides, with secondary amines (Scheme 1). Compounds 2a–e, as E/Z mixtures, have been reacted with nitrone 4. Different experimental conditions have been exploited: by reacting the nitrone and dipolarophile in
2-(1-Hydroxypropyn-2-yl)-1-vinylpyrroles: the first successful Favorsky ethynylation of pyrrolecarbaldehydes
Beilstein J. Org. Chem. 2015, 11, 228–232, doi:10.3762/bjoc.11.25
- .11.25 Abstract 1-Vinylpyrrole-2-carbaldehydes react with acetylene at atmospheric pressure in a NaOH/EtOH/DMSO system at 7–10 °C to afford 2-(1-hydroxypropyn-2-yl)-1-vinylpyrroles in 53–94% yield. Thus, the first base-mediated direct ethynylation of pyrrolecarbaldehydes with free acetylene under
- modified conditions of the Favorsky reaction has been implemented to pave an expedient route to important biomolecules containing a pyrrole ring. Keywords: acetylene; ethynylation; Favorsky reaction; 1-vinylpyrrole-2-carbaldehyde; Introduction Functionalized pyrroles bearing a terminal acetylenic moiety
- synthesized exclusively by the addition of ethynylmagnesium halides (Iotsich complexes [6]) to pyrrole-2-carbaldehydes [4][7][8]. Astonishingly, the classic Favorsky ethynylation of pyrrole aldehydes with alkynes in the presence of KOH proves to be absolutely invalid. In fact, our attempt to ethynylate
On the proposed structures and stereocontrolled synthesis of the cephalosporolides
Beilstein J. Org. Chem. 2012, 8, 1287–1292, doi:10.3762/bjoc.8.146
- ]. DDQ oxidation of PMB ether produced 1,3-dioxane 15 [37]. Protecting group manipulation led to the formation of primary alcohol 17 [38], which was converted into homopropargyl silyl ether 19 over two steps, i.e., DMP oxidation and subsequent Ohira–Bestmann ethynylation [39]. Coupling of the propargyl
One-pot gold-catalyzed synthesis of 3-silylethynyl indoles from unprotected o-alkynylanilines
Beilstein J. Org. Chem. 2011, 7, 565–569, doi:10.3762/bjoc.7.65
- conditions. We recently reported a mild procedure for the C3-selective alkynylation of indoles using AuCl and the commercially available benziodoxolone TIPS-EBX (1-[(triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one (1)) (Scheme 2) [35][36][37][38][39][40]. This methodology allowed the ethynylation of a
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