Submitted by (lucia.rodrigues@ufrpe.br) on 2017-02-13T14:05:22Z No. of bitstreams: 1 Carlos Jonnatan Pimentel Barros.pdf: 2792809 bytes, checksum: e6e2921a4590ac0ebec180e7f288314f (MD5) / Made available in DSpace on 2017-02-13T14:05:22Z (GMT). No. of bitstreams: 1 Carlos Jonnatan Pimentel Barros.pdf: 2792809 bytes, checksum: e6e2921a4590ac0ebec180e7f288314f (MD5) Previous issue date: 2012-02-13 / Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPES / In this work, we drescribed the synthesis and characterization of novel 1,2,4-oxadiazoles and 2,3-unsaturated glycosides, containing heterocyclic ring or terpene units as aglycone. The synthesis of alkyl and arylamidoximes was carried out using two methods: the first was using household microwave irradiation and the second in ultrasound-bath. The alkyl and arylamidoximes 18a-l were obtained with good yields and reduced time for the first two methods compared with the methods found in the literature. The new 1,2,4-oxadiazoles and bis-1,2,4-oxadiazoles were obtained by two methods: at reflux and by microwave irradiation. The 3-aryl-5-pentyl-1,2,4-oxadiazoles (46a-f) were obtained from methyl hexanoate. The bis-1,2,4-oxadiazoles 3,3’-aryl-5,5’-bis-1,2,4-oxadiazolyl propan-2-one (47a-h), 1,2-dihydroxy-1,2-bis [3-aryl-1,2,4-oxadiazol-5-yl]-ethane (48a-h) and 1,2-bis-(3-aryl-1,2,4-oxadiazol-5-yl)ethanol (49a-h) were obtained from the following esters, respectively: diethyl 3-oxoglutarate, dimethyl malate and diethyl tartarate. The novel 2,3-unsaturated O-glycosides were obtained from the Ferrier rearrangement of tri-O-acetyl-D-glucal with alcohols: 2-(3-thienyl)ethanol, citronellol and geraniol. The glycosides were subjected to reactions of basic hydrolysis and allylic oxidation. The structures of the compounds obtained were elucidated by conventional spectroscopic techniques: Infrared and Magnetic Nuclear Resonance 1H and 13C. / Neste trabalho, foi descrito a síntese e caracterização de inéditos 1,2,4-oxadiazóis e O-glicosídeos 2,3-insaturados, contendo anel heterocíclico ou unidades terpênicas como aglicona. A síntese de alquil e arilamidoximas foi realizada através de duas metodologias: a primeira consistiu na utilização de irradiação de microondas doméstico, a segunda em banho de ultrassom. As alquil e arilamidoximas 18a-l foram obtidas com bons rendimentos (40-92%) em tempos reduzidos quando comparado os dois primeiros métodos com os métodos encontrados na literatura. Os novos 1,2,4-oxadiazóis e bis-1,2,4-oxadiazóis foram obtidos através de duas metodologias: em refluxo e por irradiação de microondas. Os 3-aril-5-pentil-1,2,4-oxadiazóis (46a-f) foram obtidos a partir do hexanoato de metila e os bis-1,2,4-oxadiazóis 3,3’-aril-5,5’-bis-1,2,4-oxadiazolil propan-2-ona (47a-h), 1,2-diidroxi-1,2-bis[3-aril-1,2,4-oxadiazol-5-il]-etano (48a-h) e 1,2-bis-(3-aril-1,2,4-oxadiazol-5-il)-etanol (49a-h) foram obtidos a partir dos seguintes ésteres, respectivamente: 3-oxoglutarato de dietila, tartarato de dietila e malato de dimetila. Os O-glicosídeos 2,3-insaturados inéditos foram obtidos a partir do Rearranjo de Ferrier do tri-O-acetil-D-glucal com os álcoois: 2-(3-tienil)etanol, geraniol e citronelol . Os glicosídeos obtidos foram submetidos à reação de hidrólise básica e de oxidação alílica. As estruturas compostos obtidos foram elucidadas através de técnicas espectroscópicas convencionais: Infravermelho e Ressonância Magnética Nuclear de 1H e 13C.