Síntesis y estudio fotoquímico de los derivados de 3-(E)-alquenil-4-metoxifenilacetanilidas y 2-(E)-alquenil-4-nitroanisoles
This work presents the synthesis and photochemical study of 3-(E)-alkenyl-4-methoxyphenylacetanilide 3a-c and 2-(E)-alkenyl-4-nitroanisole 3d-f derivatives. These compounds were prepared using the palladium catalyzed cross-coupling Suzuki-Miyaura type reaction of 4-methoxy-2-bromo-phenylacetanilid...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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Universidad de Los Andes
2013-05-01
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| Series: | Avances en Química |
| Subjects: | |
| Online Access: | http://www.saber.ula.ve/bitstream/123456789/37140/1/nota1.pdf |
| _version_ | 1818163156887797760 |
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| author | Neudo Urdaneta Amalia Franco Nieves Canudas Debora Deutsch Julio Herrera |
| author_facet | Neudo Urdaneta Amalia Franco Nieves Canudas Debora Deutsch Julio Herrera |
| author_sort | Neudo Urdaneta |
| collection | DOAJ |
| description | This work presents the synthesis and photochemical study of 3-(E)-alkenyl-4-methoxyphenylacetanilide 3a-c and 2-(E)-alkenyl-4-nitroanisole 3d-f derivatives. These compounds were prepared using the palladium catalyzed cross-coupling Suzuki-Miyaura type reaction of 4-methoxy-2-bromo-phenylacetanilide (1a), 2-bromo-4-nitro-anisol (1b) and three E-1-alkenylboronic acids (2a-c). Compounds 3a and 3e were photolabile in 2-propanol. Molar extinction coefficients of 3a and 3e were 300.7M-1
cm-1 (λmax 315nm) and 1505 M-1 cm-1 (λmax 295nm), respectively. Photodegradation of 3e yielded 2-methoxy-5-nitrobenzaldehyde, which was likely produced by oxidative rupture of the exocyclic double bond. |
| first_indexed | 2024-12-11T16:45:05Z |
| format | Article |
| id | doaj.art-711295750d014a1291e143b7171b4394 |
| institution | Directory Open Access Journal |
| issn | 1856-5301 |
| language | English |
| last_indexed | 2024-12-11T16:45:05Z |
| publishDate | 2013-05-01 |
| publisher | Universidad de Los Andes |
| record_format | Article |
| series | Avances en Química |
| spelling | doaj.art-711295750d014a1291e143b7171b43942022-12-22T00:58:14ZengUniversidad de Los AndesAvances en Química1856-53012013-05-01814145Síntesis y estudio fotoquímico de los derivados de 3-(E)-alquenil-4-metoxifenilacetanilidas y 2-(E)-alquenil-4-nitroanisolesNeudo Urdaneta0Amalia Franco1Nieves Canudas2Debora Deutsch3Julio Herrera4Departamento de Química, Universidad Simón Bolívar, Laboratorio de Síntesis Orgánica 210. Apartado Postal 89000, Caracas, Venezuela. Departamento de Química, Universidad Simón Bolívar, Laboratorio de Síntesis Orgánica 210. Apartado Postal 89000, Caracas, Venezuela. Departamento de Química, Universidad Simón Bolívar, Laboratorio de Síntesis Orgánica 210. Apartado Postal 89000, Caracas, Venezuela. Departamento de Química, Universidad Simón Bolívar, Laboratorio de Síntesis Orgánica 210. Apartado Postal 89000, Caracas, Venezuela. Departamento de Química, Universidad Simón Bolívar, Laboratorio de Síntesis Orgánica 210. Apartado Postal 89000, Caracas, Venezuela. This work presents the synthesis and photochemical study of 3-(E)-alkenyl-4-methoxyphenylacetanilide 3a-c and 2-(E)-alkenyl-4-nitroanisole 3d-f derivatives. These compounds were prepared using the palladium catalyzed cross-coupling Suzuki-Miyaura type reaction of 4-methoxy-2-bromo-phenylacetanilide (1a), 2-bromo-4-nitro-anisol (1b) and three E-1-alkenylboronic acids (2a-c). Compounds 3a and 3e were photolabile in 2-propanol. Molar extinction coefficients of 3a and 3e were 300.7M-1 cm-1 (λmax 315nm) and 1505 M-1 cm-1 (λmax 295nm), respectively. Photodegradation of 3e yielded 2-methoxy-5-nitrobenzaldehyde, which was likely produced by oxidative rupture of the exocyclic double bond.http://www.saber.ula.ve/bitstream/123456789/37140/1/nota1.pdfSynthesisphotochemical studies3-(E)-alkenyl-4-methoxiphenylacetanilide2-(E)-alkenyl-4-nitroanisole |
| spellingShingle | Neudo Urdaneta Amalia Franco Nieves Canudas Debora Deutsch Julio Herrera Síntesis y estudio fotoquímico de los derivados de 3-(E)-alquenil-4-metoxifenilacetanilidas y 2-(E)-alquenil-4-nitroanisoles Avances en Química Synthesis photochemical studies 3-(E)-alkenyl-4-methoxiphenylacetanilide 2-(E)-alkenyl-4-nitroanisole |
| title | Síntesis y estudio fotoquímico de los derivados de 3-(E)-alquenil-4-metoxifenilacetanilidas y 2-(E)-alquenil-4-nitroanisoles |
| title_full | Síntesis y estudio fotoquímico de los derivados de 3-(E)-alquenil-4-metoxifenilacetanilidas y 2-(E)-alquenil-4-nitroanisoles |
| title_fullStr | Síntesis y estudio fotoquímico de los derivados de 3-(E)-alquenil-4-metoxifenilacetanilidas y 2-(E)-alquenil-4-nitroanisoles |
| title_full_unstemmed | Síntesis y estudio fotoquímico de los derivados de 3-(E)-alquenil-4-metoxifenilacetanilidas y 2-(E)-alquenil-4-nitroanisoles |
| title_short | Síntesis y estudio fotoquímico de los derivados de 3-(E)-alquenil-4-metoxifenilacetanilidas y 2-(E)-alquenil-4-nitroanisoles |
| title_sort | sintesis y estudio fotoquimico de los derivados de 3 e alquenil 4 metoxifenilacetanilidas y 2 e alquenil 4 nitroanisoles |
| topic | Synthesis photochemical studies 3-(E)-alkenyl-4-methoxiphenylacetanilide 2-(E)-alkenyl-4-nitroanisole |
| url | http://www.saber.ula.ve/bitstream/123456789/37140/1/nota1.pdf |
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