Síntese e ciclofuncionalização de Î²-cetoamidas e Î²-hidroxiamidas substituídas: diidrofuranos e tetraidrofuranos

Silva, Diogo de Oliveira

doi:10.11606/T.9.2003.tde-03042007-093737

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Thèse de Doctorat

DOI

https://doi.org/10.11606/T.9.2003.tde-03042007-093737

Document

Thèse de Doctorat

Auteur

Silva, Diogo de Oliveira (Catálogo USP)

Nom complet

Diogo de Oliveira Silva

Adresse Mail

Unité de l'USP

Faculdade de Ciências Farmacêuticas

Domain de Connaissance

Matières Premières à Usage Pharmaceutique

Date de Soutenance

2003-12-10

Editeur

São Paulo, 2003

Directeur

Stefani, Hélio Alexandre (Catálogo USP)

Jury

Stefani, Hélio Alexandre (Président)
Albuquerque, Cristina Northfleet de
Braga, Antonio Luiz
Melo, Robson Lopes de
Petragnani, Nicola

Titre en portugais

Síntese e ciclofuncionalização de β-cetoamidas e β-hidroxiamidas substituídas: diidrofuranos e tetraidrofuranos

Mots-clés en portugais

Beta-cetoamidas
Beta-hidroxiamidas
Ciclofuncionalização
Diidrofuranos
Tetraidrofuranos

Resumé en portugais

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.

Titre en anglais

Synthesis and cyclofunctionalization of substituted β-ketoamides and β-hydroxyamides: dihydrofurans and tetrahydrofurans

Mots-clés en anglais

Beta-hydroxyamides
Beta-ketoamides
Cyclofunctionalization
Dihydrofurans
Tetrahydrofurans

Resumé en anglais

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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Date de Publication

2007-04-16

Œvres dérivées

AVERTISSEMENT: Le matériau se réfère à des documents provenant de cette thèse ou mémoire. Le contenu de ces documents est la responsabilité de l'auteur de la thèse ou mémoire.

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