Synthesis of 3′‐1,2,4‐triazolo‐ and 3′‐1,3,4‐thiadiazoliminothymidines

Abstract

3,

Synthesis and anti‐HIV Activity of Substituted 1,2,4‐Triazolo‐thiophene Derivatives.

“…Compounds 8a-d were identified by the 1 H and 13 C NMR spectra, which are in agreement with those of the triazole analogues obtained previously [14][15][16][17][18][19][20][21][22][23][24][25]. The CH 2 signal appeared as a singlet at the region δ H 3.93-4.17 ppm.…”

1,2,4-Triazoles: Synthetic approaches and pharmacological importance. (Review)

“…Deblocking of 102 with NaOMe in MeOH at room temperature proceeded smoothly to give the free nucleosides 103; their structures were confirmed by 2D-NMR spectroscopy (Scheme 25). A new 5'-acetyl-3'-(1,3,4-thiadiazolimino)thymidine, 105, was prepared [143] via spontaneous rearrangements by cycloaddition of 5'-acetyl-3'-isothiocyanatothymidine 104 [144,145] with the reactive cumulene 93a. Although the concerted cycloaddition to isothiocyanates is known to occur both on the C=S and the C=N bond in a competitive manner [146], the cycloaddition in such reaction occurred via the C=S and not the N=C bond.…”

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.…”