Studies on v-triazoles. Part 4. The 4-methoxybenzyl group, a versatile N-protecting group for the synthesis of N-unsubstituted v-triazoles was written by Buckle, Derek R.;Rockell, Caroline J. M.. And the article was included in Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) in 1982.Safety of Ethyl 1H-1,2,3-triazole-5-carboxylate This article mentions the following:
(EtO2C)2CH2 underwent cyclocondensation with 4-MeOC6H4CH2N3 (I) to give 67% triazole II (R = OH, R1 = CH2C6H4OMe-4), which on subsequent treatment with PCl5 in PhMe at 40° gave 65% II (R = Cl, R1 as before) (III). III readily underwent halogen displacement to give 66-82% II (R = CN, 4-MeOC6H4S, PhO, R1 = CH2C6H4OMe-4). I also underwent 1,3-dipolar addition with acetylenes; thus, I with RCCCO2Et (R = H, Ph) gave 30-45% II (R as before, R1 = CH2C6H4OMe-4). Deprotection of II (R = OH, Cl, CN, H, 4-MeOC6H4S, PhO, Ph, R1 = CH2C6H4OMe-4) followed by treatment with CF3CO2H at 65° gave 52-100% II (R as before, R1 = H). In addition, hydrolysis of II (R = PhO, R1 = CH2C6H4OMe-4) gave 90% of the corresponding acid which was converted via its acyl chloride into the tricyclic compound IV (R = CH2C6H4OMe-4), analogous deprotection of which gave 70% IV (R = H), a potential antiallergic agent. In the experiment, the researchers used many compounds, for example, Ethyl 1H-1,2,3-triazole-5-carboxylate (cas: 40594-98-7Safety of Ethyl 1H-1,2,3-triazole-5-carboxylate).
Ethyl 1H-1,2,3-triazole-5-carboxylate (cas: 40594-98-7) belongs to triazole derivatives. Triazoles are important five-member nitrogen heterocycles involved in a wide range of industrial applications such as agrochemicals, corrosion inhibitors, dyes, optical brighteners, as well as biologically active agents. Many triazoles have antifungal effects: the triazole antifungal drugs include fluconazole, isavuconazole, itraconazole, voriconazole, pramiconazole, ravuconazole, and posaconazole and triazole plant-protection fungicides include epoxiconazole, triadimenol, myclobutanil, propiconazole, prothioconazole, metconazole, cyproconazole, tebuconazole, flusilazole and paclobutrazol.Safety of Ethyl 1H-1,2,3-triazole-5-carboxylate
Referemce:
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics