Table 2 Optimization of experimental conditions for the synthesis of 1,2,3-triazole derivatives in water
Related Figures (12)
Scheme 1 Synthesis of calix[4]resorcinarene 1 and the 3D-network polymer 2. To achieve this objective, the 3D-network polymer 2 was prepared by the reaction of resorcinol and acetaldehyde, fol- lowed by the polycondensation of calix[4]resorcinarene 1 with formaldehyde” as outlined in Scheme 1. In a small Schlenk tube, amine-functionalized polymer 3 (1.0 ¢ was mixed with Cul (0.017 g, 0.1 mmol) in DMF (5 mL). The mixture was stirred for 4 h under a N, atmosphere at r.t. The solid was isolated by filtration and washed consecutively with acetone (5 mL) and MeOH (5 mL). Finally the resultant product was dried at r.t. for 16 h. Table 1 Optimization of reaction conditions in the preparation of novel amine functionalized polymer 3 The formation of amine functionalized polymer 3 is of considerable interest since it is the first example of loading of basic groups as well as acidic groups” on the 3D-network polymer based on calix[4]resorcinarene. It is noteworthy to highlight that the nitrogen analysis o supported amine 3 (N, 4.95%) indicates that 3.5 mmol of the amine moieties were grafted onto the surface per 1 g of the polymer which show more potential for covalently anchored amine moieties than most previously reported solid-supports.” Furthermore, the amine polymer 3 is effectively insoluble in various solvents, including water, methanol, ethanol, dimethy sulfoxide, N,N-dimethylformamide, acetonitrile, dichloro: methane, and chloroform. These properties make polymer 3 suitable for being used as an efficient solid-supported reagent or catalyst in various reaction media. Scheme 2. Synthesis of amine functionalized polymer 3. Scanning electron microscope of the functionalized polymer 3 was undertaken on a FE-SEM (MIRA3 TESCAN) instrument (Fig. 3). The SEM images confirmed that the average size of pores is in agreement with the AFM data. Fig. 1 AFM images (1.0 um x 1.0 um) of amine functionalized polymer 3, (a) 2D and (b) 3D height and phase plots. Fig.2 Image profile (the analysis of the height along a linear path) of amine functionalized polymer 3 Fig. 4 TGA profile of amine functionalized polymer 3. Fig. 3 SEM image of amine functionalized polymer 3. Scheme 3 Synthesis of 3D-network polymer-supported Cu() catalyst 4. ¥ “~ e The copper content of catalyst, measured by a GBC Avanta, Australia, atomic absorption spectrophotometer (AAS), showed the value of about 1.26 percent of the resulted catalyst (0.2 mmol Cu per gram of the dry polymer-supported catalyst 4). Fig.5 EDS analysis of 3D-network polymer-supported Cu(i) catalyst 4. Table 3 Conversion of various alkyl/aryl halides 5, sodium azide and alkynes 6 into the corresponding 1,2,3-triazoles 7 in the presence of catalyst 4 in water Table 4 The comparison of catalyst 4 with reported catalysts in the synthesis of triazoles Fig.6 Recyclability of catalyst 4. It is well known that the reusability of a catalytic system is the key factors that identify whether it has potential applica- tions in industry. Considering this fact, in order to test the catalyst reusability, the reaction of model substrates in the presence of catalyst 4 was carried out under optimal reaction conditions. After completion of each reaction, the catalyst was recovered by simple filtration through a sintered glass-bed,
![Scheme 1 Synthesis of calix[4]resorcinarene 1 and the 3D-network polymer 2. To achieve this objective, the 3D-network polymer 2 was prepared by the reaction of resorcinol and acetaldehyde, fol- lowed by the polycondensation of calix[4]resorcinarene 1 with formaldehyde” as outlined in Scheme 1. In a small Schlenk tube, amine-functionalized polymer 3 (1.0 ¢ was mixed with Cul (0.017 g, 0.1 mmol) in DMF (5 mL). The mixture was stirred for 4 h under a N, atmosphere at r.t. The solid was isolated by filtration and washed consecutively with acetone (5 mL) and MeOH (5 mL). Finally the resultant product was dried at r.t. for 16 h.](https://figures.academia-assets.com/105681306/figure_001.jpg)
![Table 1 Optimization of reaction conditions in the preparation of novel amine functionalized polymer 3 The formation of amine functionalized polymer 3 is of considerable interest since it is the first example of loading of basic groups as well as acidic groups” on the 3D-network polymer based on calix[4]resorcinarene.](https://figures.academia-assets.com/105681306/table_001.jpg)
