Reacciones de reducción de grupo NO2 y diazotación en esqueletos de 2,8-dioxabiciclo[3.3.1]nonanos
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2023-06-08
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Jaén: Universidad de Jaén
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[ES] Los 2,8-dioxabiciclo[3.3.1]nonanos son análogos estructurales de las proantocianidinas
diméricas tipo A, compuestos presentes en la naturaleza que tienen numerosos
beneficios para los seres vivos. Hasta la fecha no se ha desarrollado un procedimiento
sintético que permita la síntesis de estos análogos con grupos electrón donantes en su
anillo A. Así, este trabajo fin de grado se centra en el estudio de síntesis y reactividad
de 2,8-dioxabiciclo[3.3.1]nonanos con el fin de elaborar una ruta de síntesis multietapa
de estos compuestos con grupos electrón donantes, empleando sales de 6-nitroflavilio
como reactivos iniciales que permitan la preparación de 6-nitro derivados de 2,8-
dioxabiciclo[3.3.1]nonanos. Posteriormente se llevará a cabo la reducción del grupo
electrón atrayente (grupo nitro) hasta un grupo electrón donante (grupo amino) y
finalmente en la cuarta etapa se aprovechará la posibilidad de interconversión que
presentan los grupos amino aromáticos haciendo uso de reacciones de diazotación y
sustituciones nucleofílicas aromáticas.
[EN] 2,8-Dioxabicyclo[3.3.1]nonanes are structural analogues of dimeric proanthocyanidins type A, a kind of compounds that are present in nature and have numerous benefits for living beings. To the best of our knowledge, no synthetic procedure has been developed that allows the synthesis of these analogues with electron-donating groups in their A- ring. Thus, this final degree work focuses on the study of the synthesis and reactivity of 2,8-dioxabicyclo[3.3.1]nonanes in order to elaborate a multi-stage synthesis route of these compounds with electron-donating groups, using 6-nitroflavilium salts as starting reagents which allow the synthesis of 6-nitro 2,8-dioxabicyclo[3.3.1]nonane derivatives. The following step will deal with the reduction of the attracting electron group (nitro group) to a donor electron group (amino group) and finally, in the last step, the possibility of interconversion showed by aromatic amino groups will be exploited by using diazotization reactions and aromatic nucleophilic substitutions.
[EN] 2,8-Dioxabicyclo[3.3.1]nonanes are structural analogues of dimeric proanthocyanidins type A, a kind of compounds that are present in nature and have numerous benefits for living beings. To the best of our knowledge, no synthetic procedure has been developed that allows the synthesis of these analogues with electron-donating groups in their A- ring. Thus, this final degree work focuses on the study of the synthesis and reactivity of 2,8-dioxabicyclo[3.3.1]nonanes in order to elaborate a multi-stage synthesis route of these compounds with electron-donating groups, using 6-nitroflavilium salts as starting reagents which allow the synthesis of 6-nitro 2,8-dioxabicyclo[3.3.1]nonane derivatives. The following step will deal with the reduction of the attracting electron group (nitro group) to a donor electron group (amino group) and finally, in the last step, the possibility of interconversion showed by aromatic amino groups will be exploited by using diazotization reactions and aromatic nucleophilic substitutions.
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Química Orgánica