<i>C</i>-2,8,14,20-tetra(propyl)-5,11,17,23-tetrakis(N–(piperidine)methyl)calix[4]resorcinarene
Calix[4]resorcinarenes are polyhydroxylated macrocyclic compounds with four units of resorcinol. These compounds can be derivatized through modifications at the upper rim, allowing reactivity with secondary amines to produce Mannich base derivatives via Mannich-type aminomethylation reactions. In th...
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MDPI AG
2025-02-01
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| author | Victor Alfonso Niño-Ramírez Zuly Jenny Rivera-Monroy Mauricio Maldonado |
| author_facet | Victor Alfonso Niño-Ramírez Zuly Jenny Rivera-Monroy Mauricio Maldonado |
| author_sort | Victor Alfonso Niño-Ramírez |
| collection | DOAJ |
| description | Calix[4]resorcinarenes are polyhydroxylated macrocyclic compounds with four units of resorcinol. These compounds can be derivatized through modifications at the upper rim, allowing reactivity with secondary amines to produce Mannich base derivatives via Mannich-type aminomethylation reactions. In this paper, we report the reaction of <i>C</i>-tetra(propyl)calix[4]resorcinarene with piperidine in acetonitrile. The aminomethylated compound <i>C</i>-2,8,14,20-tetra(propyl)-5,11,17,23-tetrakis(N–(piperidine)methyl)calix[4]resorcinarene was obtained with a 52% yield, with an exact mass of 1044.6994 u and a mass error of 7.6 ppm. The reaction progress and product formation were monitored by RP-HPLC, and the compound was characterized using LC ESI-TOF/MS, one- and two-dimensional <sup>1</sup>H and <sup>13</sup>C NMR, and FTIR spectroscopy. Chromatographic and spectroscopy data are presented and discussed. |
| format | Article |
| id | doaj-art-4b738eaa438d4bc6a8904e0600c59182 |
| institution | DOAJ |
| issn | 1422-8599 |
| language | English |
| publishDate | 2025-02-01 |
| publisher | MDPI AG |
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| series | Molbank |
| spelling | doaj-art-4b738eaa438d4bc6a8904e0600c591822025-08-20T02:42:22ZengMDPI AGMolbank1422-85992025-02-0120251M197310.3390/M1973<i>C</i>-2,8,14,20-tetra(propyl)-5,11,17,23-tetrakis(N–(piperidine)methyl)calix[4]resorcinareneVictor Alfonso Niño-Ramírez0Zuly Jenny Rivera-Monroy1Mauricio Maldonado2Departamento de Química, Universidad Nacional de Colombia, Carrera 45 No 26-85, Building 451, Bogotá 111321, ColombiaDepartamento de Química, Universidad Nacional de Colombia, Carrera 45 No 26-85, Building 451, Bogotá 111321, ColombiaDepartamento de Química, Universidad Nacional de Colombia, Carrera 45 No 26-85, Building 451, Bogotá 111321, ColombiaCalix[4]resorcinarenes are polyhydroxylated macrocyclic compounds with four units of resorcinol. These compounds can be derivatized through modifications at the upper rim, allowing reactivity with secondary amines to produce Mannich base derivatives via Mannich-type aminomethylation reactions. In this paper, we report the reaction of <i>C</i>-tetra(propyl)calix[4]resorcinarene with piperidine in acetonitrile. The aminomethylated compound <i>C</i>-2,8,14,20-tetra(propyl)-5,11,17,23-tetrakis(N–(piperidine)methyl)calix[4]resorcinarene was obtained with a 52% yield, with an exact mass of 1044.6994 u and a mass error of 7.6 ppm. The reaction progress and product formation were monitored by RP-HPLC, and the compound was characterized using LC ESI-TOF/MS, one- and two-dimensional <sup>1</sup>H and <sup>13</sup>C NMR, and FTIR spectroscopy. Chromatographic and spectroscopy data are presented and discussed.https://www.mdpi.com/1422-8599/2025/1/M1973calix[4]resorcinarenepiperidinebenzoxazineMannich base |
| spellingShingle | Victor Alfonso Niño-Ramírez Zuly Jenny Rivera-Monroy Mauricio Maldonado <i>C</i>-2,8,14,20-tetra(propyl)-5,11,17,23-tetrakis(N–(piperidine)methyl)calix[4]resorcinarene Molbank calix[4]resorcinarene piperidine benzoxazine Mannich base |
| title | <i>C</i>-2,8,14,20-tetra(propyl)-5,11,17,23-tetrakis(N–(piperidine)methyl)calix[4]resorcinarene |
| title_full | <i>C</i>-2,8,14,20-tetra(propyl)-5,11,17,23-tetrakis(N–(piperidine)methyl)calix[4]resorcinarene |
| title_fullStr | <i>C</i>-2,8,14,20-tetra(propyl)-5,11,17,23-tetrakis(N–(piperidine)methyl)calix[4]resorcinarene |
| title_full_unstemmed | <i>C</i>-2,8,14,20-tetra(propyl)-5,11,17,23-tetrakis(N–(piperidine)methyl)calix[4]resorcinarene |
| title_short | <i>C</i>-2,8,14,20-tetra(propyl)-5,11,17,23-tetrakis(N–(piperidine)methyl)calix[4]resorcinarene |
| title_sort | i c i 2 8 14 20 tetra propyl 5 11 17 23 tetrakis n piperidine methyl calix 4 resorcinarene |
| topic | calix[4]resorcinarene piperidine benzoxazine Mannich base |
| url | https://www.mdpi.com/1422-8599/2025/1/M1973 |
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