Syntheses of C- and N-nucleosides from 1-aza-2-azoniaallene and 1,3-diaza-2-azoniaallene salts

New benzylpiperazine derivatives bearing mono‐ and bis‐dialkyl substituted 1,2,4‐triazoles

“…Such examples of our recent work are 1,2,4-triazole C-nucleosides [28,29], acyclic C-nucleosides [30], pyrimidines [31], N-alkylphthalimides [32], Dmanno-pentitol-1-yl-1,2,4-triazoles [33], 1H-indoles as well as quinolines [34], benzotriazoles [35], 3 -triazolothymidines [36], N,N -trisubstituted 1,2,4-triazolo-piperazines [37], and 1,2,4-triazole derivatives of acetic acid alkylidene hydrazides [38]. In the present study, we prepared the 3-[4-(chloromethyl)-phenyl]-1,5-dimethyl-1H-1,2,4-triazole 6a and 6c, according to our reported method during the preparation of 6b and 6d [34], from the cycloaddition of 3 to 4-cyanobenzyl chloride 1.…”

“…These compounds were identified by homo-and heteronuclear NMR spectroscopic methods, HMBC [41], and mass spectra. EXPERIMENTAL [28][29][30][31][32][33][34][35][36][37] …”

C-Glycosyl 1,2,4-triazoles: Synthesis of the 3-β-d-glucopyranosyl-1,5-disubstituted and 5-β-d-glucopyranosyl-1,3-disubstituted variants

“…16,17 However, for getting a large series of compounds, multistep synthesis of each hydrazonoyl halide and/or 2,5-disubstituted-tetrazole would be necessary. These requirements adumbrate rather labour intensive preparative work to get the precursors for both route A type syntheses.…”

“…From the former class several examples of bioactive nucleoside analogues 9 and N 1 - [10][11][12][13] as well as N 4 -glycopyranosides 14 have been known. C-Glycosyl 1,2,4-triazoles are an even more uncommon type [15][16][17][18] and only in recent years has progress been made in this field with the syntheses of 3-glycopyranosyl-5-substituted-1,2,4-triazoles as glycogen phosphorylase inhibitors for potential antidiabetic use. [19][20][21][22][23][24] As a continuation of our efforts in the above syntheses, the preparation of trisubstituted Cglycopyranosyl 1,2,4-triazoles was envisaged to generate molecules for structure-activity relationships of glycogen phosphorylase inhibitors and also for other potential biological applications.…”

C-(β-d-Glucopyranosyl)formamidrazones, formic acid hydrazides and their transformations into 3-(β-d-glucopyranosyl)-5-substituted-1,2,4-triazoles: a synthetic and computational study

“…As another alternative, reactions of glycosyl cyanides with 1-aza-2-azoniaallene salts (generated in situ from chloroalkyl azo compounds by SbCl 5 ) 22,23 or with hydrazonoyl chlorides in the presence of Yb(OTf) 3 24 furnished C-glycosyl-1,2,4-triazoles. This method was used only for the preparation of 1,3,5-trisubstituted-1,2,4-triazoles both with furanoid and pyranoid sugar rings.…”