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Master's Dissertation
DOI
10.11606/D.46.2002.tde-24102007-152630
Document
Author
Full name
Fernanda Irene Bombonato
E-mail
Institute/School/College
Knowledge Area
Date of Defense
Published
São Paulo, 2002
Supervisor
Committee
Ferraz, Helena Maria Carvalho (President)
Gruber, Jonas
Imamura, Paulo Mitsuo
Title in Portuguese
Ciclofuncionalização de β,-enamino Ésteres e β-hidróxi ésteres
Keywords in Portuguese
Ciclização eletrofílica
Diidropirróis
Dimetildioxirana
Éteres cíclicos
Iodo
Pirrolidinas
Tetraidroindóis
Abstract in Portuguese
Nosso grupo de pesquisa vem se dedicado, há vários anos, ao estudo das reações de ciclização eletrofílica de substratos insaturados que contêm um nucleófilo interno (oxigênio ou nitrogênio). Este trabalho teve como objetivo obter derivados de éteres cíclicos de cinco e seis membros diferentemente funcionalizados. Compostos 1,3-dicarbonílicos e ß-hidróxi carbonílicos, contendo dupla ligação em posição apropriada, foram submetidos à reação de ciclização mediada tanto por iodo quanto por dimetildioxirana. De maneira semelhante, ß-enamino ésteres alquenilados foram submetidos à reação de iodociclização visando à síntese de diidropirróis, pirrolidínas e tetraidroindóis. Os heterociclos funcionalizados com iodo foram submetidos à reação de desidroiodação, promovida por base, fornecendo os correspondentes produtos de eliminação.
Title in English
Electrophilic cyclization of alkenyl-substituted β-enamine esters and β-hydroxy esters
Keywords in English
Cyclic ether
Dihydropyrrols
Dimethyldioxirane
Eletrophilic cyclization
Iodine
Pyrrolidines
Tetrahydroindols
Abstract in English
Our research group has been studying, for several years, eletrophilic cyclization reactions of unsaturated substrates bearing internal nucleophiles such as oxygen or nitrogen. This work aimed to obtain five and six membered cyclic ether derivatives differently functionalized. 1,3-Dicarbonyl and ß-hydroxy carbonyl compounds bearing double bonds suitably positioned were submitted to cyclization reaction mediated by either iodine or dimethyldioxirane. Similarly, alkenyl substituted ß-enamino esters were also prepared and submitted to iodo-cyclization reaction leading to dihydropyrrols, to pyrrolidines or to tetrahydroindols. The heterocyclic compounds bearing iodine were submitted to the corresponding dehydroiodination reaction mediated by base, furnishing elimination products
 
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Publishing Date
2007-10-29
 
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