Conventional and microwave assisted synthesis of 1,4-disubstituted 1,2,3-triazoles from Huisgen cycloaddition

Abstract

In this paper the synthesis of a library of new 1,4-disubstituted 1,2,3-triazoles 1, with a variety of additional functional groups on its structure, from an in situ generated benzyl azide 2 and different alkynes and dialkynes 3 is reported. Optimal experimental conditions were established for the conventional click chemistry and for the microwave-assisted synthesis of these 1,2,3-triazoles. Comparing the results it was concluded that under microwave-assisted conditions the products are obtained in higher yields in shorter times.

On the mechanochemical synthesis of C-scorpionates with an oxime moiety and their application in the copper-catalyzed azide–alkyne cycloaddition (CuAAC) reaction

“…Chem., 2024, 48, 874-886 | 885 7.36-7.35 (3H, m, H Ph ), 7.28-7.26(2H, m, H Ph ), 5.49 (2H, s, CH 2 ), 5.04 (1H, q, J = 6.4 Hz, CH), 1.54 (3H, d, J = 6.4 Hz). Characterization in accordance with that previously reported by Sarmiento-Sanchez et al 43…”

Synthesis and Antioxidant Evaluation of Enantiomerically Pure Bis-(1,2,3-triazolylmethyl)amino Esters from Modifiedα-Amino Acids

“…After reaction workup the product was isolated with 25% yield. Thus, based on our experience in the synthesis of 1,2,3-triazoles [ 46 , 47 ], the temperature reaction was increased to 60°C and the product was identified by TLC after 12 h and at 48 h the product 6a was isolated with 65% yield.…”

“…Recently, we have reported the synthesis of new enantiomerically pure compounds from chemical modifications of α -amino acids [ 43 – 45 ]. Continuing our research interest in triazoles chemistry [ 46 , 47 ], now we report our efforts in the synthesis of new enantiopure 1,4-disubstituted 1,2,3-triazoles via conventional Huisgen cycloaddition using α -halomethyl ketones 10 and α - N,N -dipropargylamino esters 11 as one strategy for coupling in solution two enantiopure moieties derived from α -amino acids. From a combinatorial chemistry approach, the methodology developed in the present work could allow preparing a library of analogues, depending on the number and nature of α -amino acids synthetically modified.…”

O‐(Triazolyl)methyl Carbamates as a Novel and Potent Class of Fatty Acid Amide Hydrolase (FAAH) Inhibitors

“…Then, copper catalyzed [3+2] cycloaddition reaction between azides 5 a and 5 b with the commercially available but-3-yn-1ol, allowed us to obtain compounds 31 a and 31 b in acceptable yields. [24] Finally, compounds 32 and 33 were prepared by coupling alcohols 31 a and 31 b, respectively, with commercial cyclohexyl isocyanate (Scheme 2). O-(1,2,3-Triazol-4-yl)methyl carbamate derivatives 20-30 (Scheme 2) were prepared by reaction of azides 6-16 with prop-2-yn-1-yl N-cyclohexylcarbamate, under click chemistry conditions.…”