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Graphical AbstractChemistry of Iminium Salts, Imines, and Related Compounds
Iminium salt structures are widespread in nature and play an important role in biochemical processes. Among these thiamine diphosphate (ThPP, Vitamine B1) is one of the best known examples. It serves as a cofactor in a variety of different enzymes that are found in all forms of life. During...
By reaction of heterocyclic-substituted 1-azo-naphth-2-ols with the Vilsmeier reagent or with strong acids polycyclic azolo[1,2,4]triazinium salts are formed in good yields. The azolo[1,2,4] triazinium salts exhibit similar UV=Vis absorption properties as the starting azo compounds, but in...
The preparation of new substituted methyl 3-azidothieno[2,3-b]pyridine carboxylates by azotization of methyl 3-aminothieno[2,3-b]pyridine and subsequent treatment with sodium azide is described. Via Huisgen’s 1,3-dipolar cycloaddition between substituted alkynes and the prepared azides, methyl...
1,3-Dimethylthymine can be prepared in a single-step reaction by heating a mixture of N-methylpropionamide and the Bredereck-Simchen reagent [tert-butyloxy-bis(dimethylamino) methane].
Tris(chloromethyl)amine (4) can be prepared by chloromethylation of urotropin with paraformaldehyde or 1,3,5-trioxane and ethyl-trichlorosilane in good yields. Photochlorination of tris(chloromethyl)amine affords tris(dichloromethyl)amine (2). Both reactions can be performed on large scale.
N;N;N';N'-Tetraformylhydrazine (3) can be pepared in good yields by heating of N;N'-diformylhydrazine (5) with N;N-diformylacetamide (6). The reaction of methanesulfonyl chloride with sodium diformamide (10) in a molar ratio of 2 : 5 in acetonitrile affords tris(diformylamino)methane...
A phenothiazinyl donor moiety can be covalently coupled to aromatic hydrocarbon acceptor units via Ugi four-component reaction in an efficient, rapid, and highly convergent fashion. These novel phenothiazine-acceptor dyads are electronically decoupled in the electronic ground state according to...
Herein a simple one-pot metal-free synthesis of 2,4,5-trisubstituted pyridines and pyridine Noxides by [2+2] cycloaddition of enaminones, which are prepared in situ from alkyl, aryl and heteroaryl methyl ketones using N,N-dimethylformamide dimethyl acetal (DMFDMA), and propyne iminium salts as...
The reaction of equimolar amounts of propyne iminium trifluoromethanesulfonates 1a, b and isoquinoline yielded, after hydrolytic work-up, the N-(3-oxoprop-1-en-1-yl)isoquinolinium salts 4a, b in modest yields. Monitoring of the reaction by 1H NMR spectroscopy indicated the formation of salts 4,...
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