2-Benzyl-7-(4-chlorophenyl)-3-morpholino-6-((1-phenyl-1<i>H</i>-1,2,3-triazol-4-yl)methyl)-6,7-dihydro-5<i>H</i>-pyrrolo[3,4-<i>b</i>]pyridin-5-one
The new polyheterocyclic compound, 2-benzyl-7-(4-chlorophenyl)-3-morpholino-6-((1-phenyl-1<i>H</i>-1,2,3-triazol-4-yl)methyl)-6,7-dihydro-5<i>H</i>-pyrrolo[3,4-<i>b</i>]pyridin-5-one, was synthesized by a sequential combination of 4-chlorobenzaldehyde, (1-phenyl-1...
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MDPI AG
2023-07-01
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| Online Access: | https://www.mdpi.com/1422-8599/2023/3/M1693 |
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| author | Perla Islas-Jácome Cecilia García-Falcón Sandra L. Castañón-Alonso Ernesto Calderón-Jaimes Daniel Canseco-González Alejandro Islas-Jácome Eduardo González-Zamora |
| author_facet | Perla Islas-Jácome Cecilia García-Falcón Sandra L. Castañón-Alonso Ernesto Calderón-Jaimes Daniel Canseco-González Alejandro Islas-Jácome Eduardo González-Zamora |
| author_sort | Perla Islas-Jácome |
| collection | DOAJ |
| description | The new polyheterocyclic compound, 2-benzyl-7-(4-chlorophenyl)-3-morpholino-6-((1-phenyl-1<i>H</i>-1,2,3-triazol-4-yl)methyl)-6,7-dihydro-5<i>H</i>-pyrrolo[3,4-<i>b</i>]pyridin-5-one, was synthesized by a sequential combination of 4-chlorobenzaldehyde, (1-phenyl-1<i>H</i>-1,2,3-triazol-4-yl)methanamine, 2-isocyano-1-morpholino-3-phenylpropan-1-one, and maleic anhydride under a microwave-assisted one-pot process [Ugi-Zhu/aza Diels-Alder cycloaddition/<i>N</i>-acylation/decarboxylation/dehydration] with a 28% overall yield. The synthesized compound was fully characterized by 1D (<sup>1</sup>H, <sup>13</sup>C) and 2D (COSY, HSQC, and HMBC) NMR, FT-IR, and HRMS. |
| first_indexed | 2024-03-10T22:26:05Z |
| format | Article |
| id | doaj.art-64d40f9beff145caa663dbb3d5176139 |
| institution | Directory Open Access Journal |
| issn | 1422-8599 |
| language | English |
| last_indexed | 2024-03-10T22:26:05Z |
| publishDate | 2023-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molbank |
| spelling | doaj.art-64d40f9beff145caa663dbb3d51761392023-11-19T12:06:44ZengMDPI AGMolbank1422-85992023-07-0120233M169310.3390/M16932-Benzyl-7-(4-chlorophenyl)-3-morpholino-6-((1-phenyl-1<i>H</i>-1,2,3-triazol-4-yl)methyl)-6,7-dihydro-5<i>H</i>-pyrrolo[3,4-<i>b</i>]pyridin-5-onePerla Islas-Jácome0Cecilia García-Falcón1Sandra L. Castañón-Alonso2Ernesto Calderón-Jaimes3Daniel Canseco-González4Alejandro Islas-Jácome5Eduardo González-Zamora6Departamento de Química, Universidad Autónoma Metropolitana-Iztapalapa, Av. Ferrocarril San Rafael Atlixco 186, Col. Leyes de Reforma 1A Sección, Iztapalapa C.P. 09310, MexicoDepartamento de Química, Universidad Autónoma Metropolitana-Iztapalapa, Av. Ferrocarril San Rafael Atlixco 186, Col. Leyes de Reforma 1A Sección, Iztapalapa C.P. 09310, MexicoLaboratorio de Investigación en Inmunoquímica, Unidad de Investigación en Inmunología Proteómica, Hospital Infantil de México Federico Gómez, Dr. Márquez 162, Col. Doctores, Cuauhtémoc C.P. 06720, MexicoLaboratorio de Investigación en Inmunoquímica, Unidad de Investigación en Inmunología Proteómica, Hospital Infantil de México Federico Gómez, Dr. Márquez 162, Col. Doctores, Cuauhtémoc C.P. 06720, MexicoConsejo Nacional de Ciencia y Tecnología—Laboratorio Nacional de Investigación y Servicio Agroalimentario y Forestal, Universidad Autónoma Chapingo, Km. 38.5 Carretera México-Texcoco, Chapingo C.P. 56230, MexicoDepartamento de Química, Universidad Autónoma Metropolitana-Iztapalapa, Av. Ferrocarril San Rafael Atlixco 186, Col. Leyes de Reforma 1A Sección, Iztapalapa C.P. 09310, MexicoDepartamento de Química, Universidad Autónoma Metropolitana-Iztapalapa, Av. Ferrocarril San Rafael Atlixco 186, Col. Leyes de Reforma 1A Sección, Iztapalapa C.P. 09310, MexicoThe new polyheterocyclic compound, 2-benzyl-7-(4-chlorophenyl)-3-morpholino-6-((1-phenyl-1<i>H</i>-1,2,3-triazol-4-yl)methyl)-6,7-dihydro-5<i>H</i>-pyrrolo[3,4-<i>b</i>]pyridin-5-one, was synthesized by a sequential combination of 4-chlorobenzaldehyde, (1-phenyl-1<i>H</i>-1,2,3-triazol-4-yl)methanamine, 2-isocyano-1-morpholino-3-phenylpropan-1-one, and maleic anhydride under a microwave-assisted one-pot process [Ugi-Zhu/aza Diels-Alder cycloaddition/<i>N</i>-acylation/decarboxylation/dehydration] with a 28% overall yield. The synthesized compound was fully characterized by 1D (<sup>1</sup>H, <sup>13</sup>C) and 2D (COSY, HSQC, and HMBC) NMR, FT-IR, and HRMS.https://www.mdpi.com/1422-8599/2023/3/M1693multicomponent reactions (MCRs)Ugi-Zhu reaction (UZ-3CR)polyheterocyclespyrrolo[3,4-<i>b</i>]pyridin-5-ones1<i>H</i>-1,2,3-triazoles |
| spellingShingle | Perla Islas-Jácome Cecilia García-Falcón Sandra L. Castañón-Alonso Ernesto Calderón-Jaimes Daniel Canseco-González Alejandro Islas-Jácome Eduardo González-Zamora 2-Benzyl-7-(4-chlorophenyl)-3-morpholino-6-((1-phenyl-1<i>H</i>-1,2,3-triazol-4-yl)methyl)-6,7-dihydro-5<i>H</i>-pyrrolo[3,4-<i>b</i>]pyridin-5-one Molbank multicomponent reactions (MCRs) Ugi-Zhu reaction (UZ-3CR) polyheterocycles pyrrolo[3,4-<i>b</i>]pyridin-5-ones 1<i>H</i>-1,2,3-triazoles |
| title | 2-Benzyl-7-(4-chlorophenyl)-3-morpholino-6-((1-phenyl-1<i>H</i>-1,2,3-triazol-4-yl)methyl)-6,7-dihydro-5<i>H</i>-pyrrolo[3,4-<i>b</i>]pyridin-5-one |
| title_full | 2-Benzyl-7-(4-chlorophenyl)-3-morpholino-6-((1-phenyl-1<i>H</i>-1,2,3-triazol-4-yl)methyl)-6,7-dihydro-5<i>H</i>-pyrrolo[3,4-<i>b</i>]pyridin-5-one |
| title_fullStr | 2-Benzyl-7-(4-chlorophenyl)-3-morpholino-6-((1-phenyl-1<i>H</i>-1,2,3-triazol-4-yl)methyl)-6,7-dihydro-5<i>H</i>-pyrrolo[3,4-<i>b</i>]pyridin-5-one |
| title_full_unstemmed | 2-Benzyl-7-(4-chlorophenyl)-3-morpholino-6-((1-phenyl-1<i>H</i>-1,2,3-triazol-4-yl)methyl)-6,7-dihydro-5<i>H</i>-pyrrolo[3,4-<i>b</i>]pyridin-5-one |
| title_short | 2-Benzyl-7-(4-chlorophenyl)-3-morpholino-6-((1-phenyl-1<i>H</i>-1,2,3-triazol-4-yl)methyl)-6,7-dihydro-5<i>H</i>-pyrrolo[3,4-<i>b</i>]pyridin-5-one |
| title_sort | 2 benzyl 7 4 chlorophenyl 3 morpholino 6 1 phenyl 1 i h i 1 2 3 triazol 4 yl methyl 6 7 dihydro 5 i h i pyrrolo 3 4 i b i pyridin 5 one |
| topic | multicomponent reactions (MCRs) Ugi-Zhu reaction (UZ-3CR) polyheterocycles pyrrolo[3,4-<i>b</i>]pyridin-5-ones 1<i>H</i>-1,2,3-triazoles |
| url | https://www.mdpi.com/1422-8599/2023/3/M1693 |
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