Reactions of 5-dialkylamino-1,2,3-thiadiazole-4-carbaldehydes with amines as a method for the synthesis of 1,2,3-triazole-4-carbothioamides

Synthesis of New 4‐Vinyl‐1,2,3‐Thiadiazoles

“…A control reaction without an additive demonstrated that a catalyst is required for product formation to occur at room temperature (Table S1). It is also worth noting that mild conditions were critical to develop the condensation reaction, since 1,2,3‐thiadiazole‐4‐carbaldehydes 3 are sensitive and thermally labile compounds which can be easily deformylated on heating [15] . For this reason, mild pyrrolidinium acetate catalysis in ethanol solution was chosen as optimal to develop a general and preparatively convenient synthetic procedure.…”

“…The 1,2,3-thiadiazole-4-carbaldehydes 3 a-m required for the Knoevenagel condensation were obtained in two steps from readily available 1,2,3-thiadiazole-4-carboxylates 1 a-m [15][16] through reduction of the ester functionality and subsequent oxidation of the intermediate 4-hydroxymethyl-1,2,3-thiadiazoles 2 a-m using modified procedures (Scheme 1). [15] Due to low efficiency of the reduction step (18 % yield), the unsubstituted 1,2,3-thiadiazole-4-carbaldehyde 3 n was synthesized according to a more preparatively convenient route (see Supporting Information for details). [17] Of note, the majority of compounds are new -with seven of the synthesized 1,2,3thiadiazole-4-carboxylates 1, ten of the 4-hydroxymethyl-1,2,3-thiadiazoles 2 and nine of the 1,2,3-thiadiazole-4-carbaldehydes 3 novel compounds.…”

“…For this purpose, we also modified methods for the synthesis of various 1,2,3-thiadiazole derivatives, expanding the range of 4-carboxy-, 4-hydroxymethyl-and 4-formyl-1,2,3thiadiazoles. [15]…”

“…In this context, as a continuation of our studies, we report the synthesis of new structurally diverse 4‐vinyl‐1,2,3‐thiadiazoles. For this purpose, we also modified methods for the synthesis of various 1,2,3‐thiadiazole derivatives, expanding the range of 4‐carboxy‐, 4‐hydroxymethyl‐ and 4‐formyl‐1,2,3‐thiadiazoles [15] …”

3-(4-Thiocarbamoyl-1,2,3-triazol-1-yl)benzo-15-crown-5: synthesis and properties

“…1-3 Much attention is attracted to the synthesis of extractants that possess the ability to selectively bind such bipolar organic molecules as amino acids. 4 The present work is concerned with the synthesis of benzo 15 crown 5 ethers containing a thiocarba moyl 1,2,3 triazolyl substituent and with the extrac tion of α amino acids from water using target com pounds.aaa Earlier, 5, 6 we have demonstrated that reactions of 1,2,3 thiadiazole 4 carbaldehyde with amines initially produce the corresponding imines, which in situ undergo the Cornforth rearrangement to give 1 substituted 1,2,3 triazole 4 carbothioamides. We used this reaction to ob tain benzocrown ethers containing the 1,2,3 triazole ring linked via the thiocarbamoyl group.…”