Síntesis y estudio fotoquímico de los derivados de 3-(E)-alquenil-4-metoxifenilacetanilidas y 2-(E)-alquenil-4-nitroanisoles

Abstract

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.

Keywords

• Synthesis
• photochemical studies
• 3-(E)-alkenyl-4-methoxiphenylacetanilide
• 2-(E)-alkenyl-4-nitroanisole