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Doctoral Thesis
DOI
https://doi.org/10.11606/T.46.2018.tde-18092018-160100
Document
Author
Full name
Marta Regina dos Santos Nunes
Institute/School/College
Knowledge Area
Date of Defense
Published
São Paulo, 2002
Supervisor
Committee
Ferraz, Helena Maria Carvalho (President)
Baader, Josef Wilhelm
Brocksom, Ursula
Donate, Paulo Marcos
Pardini, Vera Lucia
Title in Portuguese
Ciclização eletrofílica de compostos β-enamino carbonílicos e β-dicarbonílicos
Keywords in Portuguese
Ciclização eletrofílica
Compostos cíclicos
Dicarbonílicos
Enaminonas
Reações orgânicas
Abstract in Portuguese
Esta tese consiste do estudo de reações de ciclofuncionalização de compostos β-enamino carbonílicos e β-dicarbonílicos, contendo uma cadeia alquenílica nas posições α ou γ. Os eletrófilos empregados para este fim foram: iodo, brometo de fenilselenenila e tricloreto de p-metóxifeniltelurio. Os iodo-β-enamino ésteres e cetonas cíclicas, após desidroiodação mediada por base, levaram à formação dos correspondentes pirróis, indóis e aminobenzofuranos. A ciclização dos β-ceto ésteres e β-dicetonas levou a enol éteres e benzofuranos funcionalizados. Estes resultados, juntamente com outros obtidos em nosso grupo de pesquisa, foram utilizados em um estudo comparativo entre reagentes de iodo, selênio e telúrio frente a reações de ciclização eletrofílica de substratos β-dicarbonílicos.
Title in English
Electrophilic cycling of β-enamino-carbonyl and β-dicarbonyl compounds
Keywords in English
Cyclic compounds
Dicarbonyl
Electrophilic cyclization
Enaminones
Organic reactions
Abstract in English
This thesis presents a study of the cyclofunctionalization of β-enamino carbonyl and β-dicarbonyl compounds, substituted by an alkenyl group at the α or γ positions. Iodine, phenyl-selenenyl bromide and p-methoxyphenyltellurium trichloride were employed as the electrophilic reagent. The cyclic iodo-β-enamino esters and ketones, after base-promoted dehydroiodination, led to the corresponding pyrroles, indoles and aminobenzofurans. The cyclization of the β-keto esters and β-diketones afforded five- and six-membered enol ethers and benzofuranones. These results, together with others previously obtained in our research group, allowed us to compare the behavior of the three above mentioned electrophiles toward the cyclofunctionalization of β-dicarbonyl substrates.
 
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Publishing Date
2018-09-18
 
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