Ferrocenyl-<i>bis</i>-(1-(4-benzyl-5-morpholinooxazol-2-yl)-<i>N</i>-(4-(trifluoromethyl)benzyl)methanamine)
The new <i>bis</i>-heterocyclic compound ferrocenyl-<i>bis</i>-(1-(4-benzyl-5-morpholinooxazol-2-yl)-<i>N</i>-(4-(trifluoromethyl)benzyl)methanamine) (<b>1</b>) was synthesized in 73% overall yield in 1.5 hours via a pseudo-repetitive Ugi-Zhu five-comp...
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| Format: | Article |
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MDPI AG
2022-09-01
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| Series: | Molbank |
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| Online Access: | https://www.mdpi.com/1422-8599/2022/3/M1444 |
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| author | Roberto E. Blanco-Carapia Enrique A. Aguilar-Rangel Alejandro Islas-Jácome Eduardo González-Zamora |
| author_facet | Roberto E. Blanco-Carapia Enrique A. Aguilar-Rangel Alejandro Islas-Jácome Eduardo González-Zamora |
| author_sort | Roberto E. Blanco-Carapia |
| collection | DOAJ |
| description | The new <i>bis</i>-heterocyclic compound ferrocenyl-<i>bis</i>-(1-(4-benzyl-5-morpholinooxazol-2-yl)-<i>N</i>-(4-(trifluoromethyl)benzyl)methanamine) (<b>1</b>) was synthesized in 73% overall yield in 1.5 hours via a pseudo-repetitive Ugi-Zhu five-component reaction, starting from 1,1′-ferrocenedicarboxaldehyde, 4-(trifluoromethyl)benzylamine, and 2-isocyano-1-morpholino-3-phenylpropan-1-one, in 1:2.1:2.2 proportions, respectively, using scandium(III) triflate as a Lewis-acid catalyst, microwaves as a heat source, and toluene as a solvent. The synthesized compound was characterized by 1D (<sup>1</sup>H, <sup>13</sup>C, and <sup>19</sup>F) and 2D (COSY, HSQC, and HMBC) NMR, HRMS, and FT-IR. |
| first_indexed | 2024-03-09T23:03:22Z |
| format | Article |
| id | doaj.art-d65d4facf2ec4c2bb271d793f23f79ef |
| institution | Directory Open Access Journal |
| issn | 1422-8599 |
| language | English |
| last_indexed | 2024-03-09T23:03:22Z |
| publishDate | 2022-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molbank |
| spelling | doaj.art-d65d4facf2ec4c2bb271d793f23f79ef2023-11-23T17:57:59ZengMDPI AGMolbank1422-85992022-09-0120223M144410.3390/M1444Ferrocenyl-<i>bis</i>-(1-(4-benzyl-5-morpholinooxazol-2-yl)-<i>N</i>-(4-(trifluoromethyl)benzyl)methanamine)Roberto E. Blanco-Carapia0Enrique A. Aguilar-Rangel1Alejandro Islas-Jácome2Eduardo González-Zamora3Departamento de Química, Universidad Autónoma Metropolitana-Iztapalapa, Av. Ferrocarril San Rafael Atlixco 186, Col. Leyes de Reforma 1A Sección, Iztapalapa, Ciudad de Mexico C.P. 09310, MexicoDepartamento de Química, Universidad Autónoma Metropolitana-Iztapalapa, Av. Ferrocarril San Rafael Atlixco 186, Col. Leyes de Reforma 1A Sección, Iztapalapa, Ciudad de Mexico C.P. 09310, MexicoDepartamento de Química, Universidad Autónoma Metropolitana-Iztapalapa, Av. Ferrocarril San Rafael Atlixco 186, Col. Leyes de Reforma 1A Sección, Iztapalapa, Ciudad de Mexico C.P. 09310, MexicoDepartamento de Química, Universidad Autónoma Metropolitana-Iztapalapa, Av. Ferrocarril San Rafael Atlixco 186, Col. Leyes de Reforma 1A Sección, Iztapalapa, Ciudad de Mexico C.P. 09310, MexicoThe new <i>bis</i>-heterocyclic compound ferrocenyl-<i>bis</i>-(1-(4-benzyl-5-morpholinooxazol-2-yl)-<i>N</i>-(4-(trifluoromethyl)benzyl)methanamine) (<b>1</b>) was synthesized in 73% overall yield in 1.5 hours via a pseudo-repetitive Ugi-Zhu five-component reaction, starting from 1,1′-ferrocenedicarboxaldehyde, 4-(trifluoromethyl)benzylamine, and 2-isocyano-1-morpholino-3-phenylpropan-1-one, in 1:2.1:2.2 proportions, respectively, using scandium(III) triflate as a Lewis-acid catalyst, microwaves as a heat source, and toluene as a solvent. The synthesized compound was characterized by 1D (<sup>1</sup>H, <sup>13</sup>C, and <sup>19</sup>F) and 2D (COSY, HSQC, and HMBC) NMR, HRMS, and FT-IR.https://www.mdpi.com/1422-8599/2022/3/M1444pseudo-repetitive multicomponent reactionsUgi-Zhu reactionMW-assisted reactionsferrocene1,3-Oxazolehybrid compounds |
| spellingShingle | Roberto E. Blanco-Carapia Enrique A. Aguilar-Rangel Alejandro Islas-Jácome Eduardo González-Zamora Ferrocenyl-<i>bis</i>-(1-(4-benzyl-5-morpholinooxazol-2-yl)-<i>N</i>-(4-(trifluoromethyl)benzyl)methanamine) Molbank pseudo-repetitive multicomponent reactions Ugi-Zhu reaction MW-assisted reactions ferrocene 1,3-Oxazole hybrid compounds |
| title | Ferrocenyl-<i>bis</i>-(1-(4-benzyl-5-morpholinooxazol-2-yl)-<i>N</i>-(4-(trifluoromethyl)benzyl)methanamine) |
| title_full | Ferrocenyl-<i>bis</i>-(1-(4-benzyl-5-morpholinooxazol-2-yl)-<i>N</i>-(4-(trifluoromethyl)benzyl)methanamine) |
| title_fullStr | Ferrocenyl-<i>bis</i>-(1-(4-benzyl-5-morpholinooxazol-2-yl)-<i>N</i>-(4-(trifluoromethyl)benzyl)methanamine) |
| title_full_unstemmed | Ferrocenyl-<i>bis</i>-(1-(4-benzyl-5-morpholinooxazol-2-yl)-<i>N</i>-(4-(trifluoromethyl)benzyl)methanamine) |
| title_short | Ferrocenyl-<i>bis</i>-(1-(4-benzyl-5-morpholinooxazol-2-yl)-<i>N</i>-(4-(trifluoromethyl)benzyl)methanamine) |
| title_sort | ferrocenyl i bis i 1 4 benzyl 5 morpholinooxazol 2 yl i n i 4 trifluoromethyl benzyl methanamine |
| topic | pseudo-repetitive multicomponent reactions Ugi-Zhu reaction MW-assisted reactions ferrocene 1,3-Oxazole hybrid compounds |
| url | https://www.mdpi.com/1422-8599/2022/3/M1444 |
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