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Doctoral Thesis
DOI
https://doi.org/10.11606/T.9.2003.tde-03042007-093737
Document
Author
Full name
Diogo de Oliveira Silva
E-mail
Institute/School/College
Knowledge Area
Date of Defense
Published
São Paulo, 2003
Supervisor
Committee
Stefani, Hélio Alexandre (President)
Albuquerque, Cristina Northfleet de
Braga, Antonio Luiz
Melo, Robson Lopes de
Petragnani, Nicola
Title in Portuguese
Síntese e ciclofuncionalização de β-cetoamidas e β-hidroxiamidas substituídas: diidrofuranos e tetraidrofuranos
Keywords in Portuguese
Beta-cetoamidas
Beta-hidroxiamidas
Ciclofuncionalização
Diidrofuranos
Tetraidrofuranos
Abstract in Portuguese
Os compostos heterocíclicos oxigenados possuem grande destaque devido à ocorrência em substâncias com atividade biológica, e por sua alta aplicabilidade como intermediários sintéticos e blocos de construção. Neste sentido, estudou-se a obtenção de diidrofuranos e tetraidrofuranos via ciclofuncionalização de β-cetoamidas e β-hidroxiamidas convenientemente substituídas. As metodologias envolveram agentes eletrofílicos como iodo, reagentes de selênio e telúrio, e sais de mercúrio. A preparação das β-cetoamidas α-substituídas partiu dos β-cetoésteres correspondentes. Com a finalidade de confeccionar derivados tetraidrofurânicos assimétricos, foi investigada a síntese de β-hidroxiamidas α-substituídas com controle estereoquímico. Estudou-se sistemáticas de redução diastereosseletiva de γ-sulfinil-β-cetoamidas assimétricas, reações de crômio-Reformatsky e condensação-alquilação "one pot" com enolatos de amidas quirais.
Title in English
Synthesis and cyclofunctionalization of substituted β-ketoamides and β-hydroxyamides: dihydrofurans and tetrahydrofurans
Keywords in English
Beta-hydroxyamides
Beta-ketoamides
Cyclofunctionalization
Dihydrofurans
Tetrahydrofurans
Abstract in English
Heterocyclic rings with oxygen atom possess large interest due their occurrence in biologically active compounds and their synthetic applicability in building blocks construction. In this way, it was studied the obtainment of dihydrofurans and tetrahydrofurans via cyclofunctionalization of substituted β-ketoamides and β-hydroxyamides. The methodologies applied electhophilic agents as iodine, selenium and tellurium reagents, and mercury salts. The protocol to afford the α-substituted β-ketoamides used the respective β- ketoesters as starting materials. Aiming to produce asymmetric tetrahydrofurans, it was studied the α-substituted β- hydroxyamides synthesis over stereochemistry control. To perform this propose were investigated stereocontrolled reductions of chiral γ-sulfinyl-β-ketoamides, chromium- Reformatsky aldol reactions and the one-pot condensation-alkylation protocol.
 
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Publishing Date
2007-04-16
 
WARNING: The material described below relates to works resulting from this thesis or dissertation. The contents of these works are the author's responsibility.
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