{"id":110509,"date":"2018-03-11T10:36:35","date_gmt":"2018-03-11T10:36:35","guid":{"rendered":"https:\/\/www.deberes.net\/tesis\/sin-categoria\/sa%c2%adntesis-de-meridianinas-y-aplicacion-de-la-metodologa%c2%ada-de-iminofosforanos-a-la-preparacion-de-quinazolinonas-tetraca%c2%adclicas\/"},"modified":"2018-03-11T10:36:35","modified_gmt":"2018-03-11T10:36:35","slug":"sa%c2%adntesis-de-meridianinas-y-aplicacion-de-la-metodologa%c2%ada-de-iminofosforanos-a-la-preparacion-de-quinazolinonas-tetraca%c2%adclicas","status":"publish","type":"post","link":"https:\/\/www.deberes.net\/tesis\/quimica-organica\/sa%c2%adntesis-de-meridianinas-y-aplicacion-de-la-metodologa%c2%ada-de-iminofosforanos-a-la-preparacion-de-quinazolinonas-tetraca%c2%adclicas\/","title":{"rendered":"S\u00edntesis de meridianinas y aplicaci\u00f3n de la metodolog\u00eda de iminofosforanos a la preparaci\u00f3n de quinazolinonas tetrac\u00edclicas."},"content":{"rendered":"<h2>Tesis doctoral de <strong> Juan  Antonio Bleda Sanchez <\/strong><\/h2>\n<p>En el primer cap\u00edtulo de esta memoria se describe la primera s\u00edntesis total de los alcaloides de origen marino meridianinas a, c-e y g, siendo la etapa clave la formaci\u00f3n del sistema 2-aminopirimidina en posici\u00f3n c-3 de indol, mediante ciclaci\u00f3n de la adecuada enaminona y clorhidrato de guanidina, en condiciones b\u00e1sicas, con simult\u00e1nea n-desprotecci\u00f3n de grupo tosilo. Las correspondientes enaminonas se han obtenidas por aplicaci\u00f3n del protocolo de bredereck sobre los derivados n-tosil-3-acetilindol. En este cap\u00edtulo tambi\u00e9n se realiza la primera s\u00edntesis de n-tosil-3-acetil-4-benciloxi-7-bromoindol, intermedio necesario para la preparaci\u00f3n de meridianinas a y e.  en el segundo cap\u00edtulo se describe la s\u00edntesis de sistemas tetraheteroc\u00edclicos lineales y angulares. Los sistemas lineales 6h-benzimidazo[2,1-b]quinazolin-12-onas y 12h-benzo[4,5]tiazolo[2,3-b]quinazolin-12-onas, se han preparado a partir de iminofosforanos que disponen en posici\u00f3n orto de una n-(o-sustituida)arilcarboxamida, mediante combinaci\u00f3n de la metodolog\u00eda aza-wittig\/ciclaci\u00f3n de heterocumuleno, seguida de n- y s- arilaci\u00f3n por acoplamiento intermolecular tipo ullmann catalizado con cu (i).  los sistemas tetraheteroc\u00edclicos angulares benzimidazo[1,2-c]quinazolina y quinazolino[2,3-a]quinazolina se han obtenido, a partir del adecuado iminofosforano, mediante un proceso t\u00e1ndem aza-wittig\/ciclaci\u00f3n de heterocumuleno, seguido de posterior tratamiento con diferentes agentes de reducci\u00f3n de la 3h-quinazolin-4-ona generada. Adem\u00e1s, se han preparado 4-metilen-4h-benzo[d][1,3]oxazinas por reacci\u00f3n de n-(2-acetilfenil)-2-[(trifenilfosforaniliden)amino]benzamida con isocianatos arom\u00e1ticos y alif\u00e1ticos. Esta transformaci\u00f3n supone una nueva reacci\u00f3n aza-wittig con cierre de anillo de la carbodiimida y posterior reagrupamiento inducido a trav\u00e9s de la forma enol de 4-imino-3,1-benzoxazina a 4-metilen-4h-benzo[d][1,3]oxazina.<\/p>\n<p>&nbsp;<\/p>\n<h3>Datos acad\u00e9micos de la tesis doctoral \u00ab<strong>S\u00edntesis de meridianinas y aplicaci\u00f3n de la metodolog\u00eda de iminofosforanos a la preparaci\u00f3n de quinazolinonas tetrac\u00edclicas.<\/strong>\u00ab<\/h3>\n<ul>\n<li><strong>T\u00edtulo de la tesis:<\/strong>\u00a0 S\u00edntesis de meridianinas y aplicaci\u00f3n de la metodolog\u00eda de iminofosforanos a la preparaci\u00f3n de quinazolinonas tetrac\u00edclicas. <\/li>\n<li><strong>Autor:<\/strong>\u00a0 Juan  Antonio Bleda Sanchez <\/li>\n<li><strong>Universidad:<\/strong>\u00a0 Murcia<\/li>\n<li><strong>Fecha de lectura de la tesis:<\/strong>\u00a0 22\/07\/2011<\/li>\n<\/ul>\n<p>&nbsp;<\/p>\n<h3>Direcci\u00f3n y tribunal<\/h3>\n<ul>\n<li><strong>Director de la tesis<\/strong>\n<ul>\n<li>Pilar Mart\u00ednez Fresneda<\/li>\n<\/ul>\n<\/li>\n<li><strong>Tribunal<\/strong>\n<ul>\n<li>Presidente del tribunal: josep Font cierco <\/li>\n<li>mercedes Alvarez domingo (vocal)<\/li>\n<li>esther Lete exposito (vocal)<\/li>\n<li>gabriel Garcia sanchez (vocal)<\/li>\n<\/ul>\n<\/li>\n<\/ul>\n<p>&nbsp;<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Tesis doctoral de Juan Antonio Bleda Sanchez En el primer cap\u00edtulo de esta memoria se describe la primera s\u00edntesis total [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"site-sidebar-layout":"default","site-content-layout":"","ast-site-content-layout":"","site-content-style":"default","site-sidebar-style":"default","ast-global-header-display":"","ast-banner-title-visibility":"","ast-main-header-display":"","ast-hfb-above-header-display":"","ast-hfb-below-header-display":"","ast-hfb-mobile-header-display":"","site-post-title":"","ast-breadcrumbs-content":"","ast-featured-img":"","footer-sml-layout":"","theme-transparent-header-meta":"","adv-header-id-meta":"","stick-header-meta":"","header-above-stick-meta":"","header-main-stick-meta":"","header-below-stick-meta":"","astra-migrate-meta-layouts":"default","ast-page-background-enabled":"default","ast-page-background-meta":{"desktop":{"background-color":"var(--ast-global-color-4)","background-image":"","background-repeat":"repeat","background-position":"center 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