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Síntesis alternativa de derivados dibenzazepínicos empleando aceite esencial de hierba santa (Piper auritum)
dc.rights.license | Atribución-NoComercial-SinDerivadas 4.0 Internacional |
dc.contributor.advisor | Ochoa Puentes, Cristian |
dc.contributor.advisor | Ávila Murillo, Mónica Constanza |
dc.contributor.author | Rodríguez Huerto, Paula Andrea |
dc.date.accessioned | 2023-04-27T16:00:45Z |
dc.date.available | 2023-04-27T16:00:45Z |
dc.date.issued | 2022-10-07 |
dc.identifier.uri | https://repositorio.unal.edu.co/handle/unal/83803 |
dc.description | ilustraciones, fotografías color |
dc.description.abstract | El trabajo de investigación descrito en este documento presenta los resultados obtenidos en la búsqueda de precursores sintéticos a partir de fuentes renovables y su posterior transformación química. Para cumplir con los objetivos de esta investigación se plantearon dos etapas donde la primera parte se enfocó hacia la obtención de aceite esencial de hierba santa (Piper auritum) y la segunda etapa consistió en explorar su potencial sintético dirigido hacia la obtención de derivados azepínicos. El aceite esencial de hierba santa, el cual posee un alto contenido de safrol (fenilpropanoide perteneciente a la lista de sustancias ilícitas de estupefacientes y psicoactivas en Colombia, de acuerdo con la resolución número 823 del 2003), se obtuvo por medio de hidrodestilación convencional y asistida por microondas empleando la parte aérea (hojas, tallos e inflorescencias). El aceite con el mayor contenido del fenilpropanoide (4,26 g safrol/100 g de material vegetal) y mejor calidad se obtuvo mediante idrodestilación convencional a partir de las inflorescencias colectadas en Doradal, Antioquia, con un rendimiento de extracción de 5,18 %p/p. Todos los aceites extraídos se analizaron por cromatografía de gases acoplada a espectrometría de masas (GC-MS) encontrando como componentes comunes y mayoritarios el safrol (72,68 – 89,56 %), terpinoleno y -terpineno. Una vez obtenido el aceite esencial, y con el fin de explorar su potencial sintético, se realizó una nitración (61 %) y reducción (64 %) con el fin de obtener la orto-alil anilina derivada del safrol (aminosafrol). Este precursor permitió obtener una serie de N-bencil derivados de aminosafrol con rendimientos entre 66 y 93 % mediante una reacción one-pot de condensación-reducción empleando benzaldehído y sus análogos con sustituyentes 2-metil, 4-metil, 2-metoxi, 3-metoxi, 4-metoxi, 4-dimetilamino, 4-isopropil, 2-bromo y 4-bromo. Estas aminas secundarias se emplearon por una parte para estudiar la ciclación intramolecular tipo Friedel-Crafts lo que permitió obtener un derivado de dibenzazocina con un rendimiento de 40%; por otra parte, la oxidación de una amina secundaria para generar una nitrona y su posterior ciclación intramolecular 1,3-dipolar, la cual generó diez derivados benzazepínicos con rendimientos entre 19 y 48 % para las dos etapas. En conclusión, ambas propuestas (azocinas y benzazepinas) se realizaron mediante 5 y 6 transformaciones sintéticas respectivamente, teniendo como rendimientos globales de reacción 10,4% y un rango entre 5 - 14%. (Texto tomado de la fuente) |
dc.description.abstract | The research work described in this document presents the results obtained in the search for synthetic precursors from renewable sources and their subsequent chemical transformation. To meet the objectives of this research, two stages were proposed where the first focused on obtaining essential oil from Hierba Santa (Piper auritum) and the second stage consisted of exploring its synthetic potential directed towards obtaining azepine derivatives. The essential oil of Hierba Santa, which has a high content of safrole (phenylpropanoid belonging to the list of illicit narcotic and psychoactive substances in Colombia, following resolution number 823 of 2003), was obtained employing conventional hydrodistillation and microwave-assisted use of the aerial part (leaves, stems, and inflorescences). The oil with the highest content of phenylpropanoid (4.26 g safrole/100 g of plant material) and the best quality was obtained by conventional hydrodistillation from the inflorescences collected in Doradal, Antioquia, with an extraction yield of 5.18 % w/w. All the extracted oils were analyzed by gas chromatography coupled to mass spectrometry (GC-MS), finding safrole (72.68 – 89.56 %), terpinolene, and y-terpinene as common and major components. Once the essential oil was obtained, and to explore its synthetic potential, nitration (61 %) and reduction (64 %) were performed to obtain the ortho-allyl aniline derived from safrole (aminosafrol). This precursor made it possible to obtain a series of N-benzyl aminosafrole derivatives with yields between 66 and 93 % through a one-pot condensation-reduction reaction using benzaldehyde and its analogs with 2-methyl, 4-methyl, 2-methoxy, 3- methoxy, 4-methoxy, 4-dimethylamino, 4-isopropyl, 2-bromo and 4-bromo substituents. These secondary amines were used, on the one hand, to study the intramolecular FriedelCrafts type cyclization, which allowed obtaining one dibenzazocine derivative with yield of 40%. On the other hand, the oxidation of a secondary amine to generate a nitrone and its subsequent intramolecular 1,3-dipolar cyclization, which generated ten benzazepine derivatives with yields between 19 and 48 % for the two steps. In conclusion, both proposals (azocines and benzazepines) were carried out through 5 and 6 synthetic transformations, respectively, with overall reaction yields of 10.4% and a range between 5 - 14%. |
dc.format.extent | xxiv, 123 páginas |
dc.format.mimetype | application/pdf |
dc.language.iso | spa |
dc.publisher | Universidad Nacional de Colombia |
dc.rights.uri | http://creativecommons.org/licenses/by-nc-nd/4.0/ |
dc.title | Síntesis alternativa de derivados dibenzazepínicos empleando aceite esencial de hierba santa (Piper auritum) |
dc.type | Trabajo de grado - Maestría |
dc.type.driver | info:eu-repo/semantics/masterThesis |
dc.type.version | info:eu-repo/semantics/acceptedVersion |
dc.publisher.program | Bogotá - Ciencias - Maestría en Ciencias - Química |
dc.contributor.researchgroup | Síntesis Orgánica Sostenible |
dc.contributor.researchgroup | Grupo de Investigación en Química de Productos Naturales Vegetales Bioactivos (Quipronab) |
dc.description.degreelevel | Maestría |
dc.description.degreename | Maestra en Química |
dc.description.researcharea | Química Verde y Síntesis Orgánica |
dc.identifier.instname | Universidad Nacional de Colombia |
dc.identifier.reponame | Repositorio Institucional Universidad Nacional de Colombia |
dc.identifier.repourl | https://repositorio.unal.edu.co/ |
dc.publisher.faculty | Facultad de Ciencias |
dc.publisher.place | Bogotá,Colombia |
dc.publisher.branch | Universidad Nacional de Colombia - Sede Bogotá |
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dc.rights.accessrights | info:eu-repo/semantics/openAccess |
dc.subject.decs | Plants, Medicinal |
dc.subject.decs | Plantas medicinales |
dc.subject.decs | Extractos vegetales |
dc.subject.decs | Plant Extracts |
dc.subject.proposal | Aceite esencial |
dc.subject.proposal | Piper auritum |
dc.subject.proposal | Safrol |
dc.subject.proposal | Aminosafrol |
dc.subject.proposal | dibenz[b,e]azocina |
dc.subject.proposal | Benzazepina |
dc.subject.proposal | Essential oil |
dc.subject.proposal | Piper auritum |
dc.subject.proposal | Safrole |
dc.subject.proposal | Aminosafrole |
dc.subject.proposal | Dibenzo[b,e]azozine |
dc.subject.proposal | Benzazepine |
dc.title.translated | Alternative synthesis of dibenzazepine derivatives using essential oil of yerba santa (Piper auritum) |
dc.type.coar | http://purl.org/coar/resource_type/c_bdcc |
dc.type.coarversion | http://purl.org/coar/version/c_ab4af688f83e57aa |
dc.type.content | Text |
dc.type.redcol | http://purl.org/redcol/resource_type/TM |
oaire.accessrights | http://purl.org/coar/access_right/c_abf2 |
dcterms.audience.professionaldevelopment | Estudiantes |
dcterms.audience.professionaldevelopment | Investigadores |
dcterms.audience.professionaldevelopment | Maestros |
dcterms.audience.professionaldevelopment | Público general |
dc.contributor.cvlac | RODRÍGUEZ HUERTO, PAULA ANDREA |
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