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Master's Dissertation
DOI
10.11606/D.46.1997.tde-18112015-145656
Document
Author
Full name
Fernando Luiz Cardoso Pereira
E-mail
Institute/School/College
Knowledge Area
Date of Defense
Published
São Paulo, 1997
Supervisor
Committee
Ferraz, Helena Maria Carvalho (President)
Alvarenga, Marden Antonio de
Correia, Carlos Roque Duarte
Title in Portuguese
Estudos Sobre iodociclização e desidroiodação de N-benzil-beta-enaminoésteres (OU) Estudos sobre iodociclização e desidroiodação de β-enaminoésteres
Keywords in Portuguese
Compostos de nitrogênio
Compostos de oxigênio
Físico-química Orgânica
Reações químicas
Abstract in Portuguese
Os iodo-β-enaminoésteres cíclicos 13, 14, 15 e 16 (heterociclos nitrogenados de 5 membros) foram preparados pela iodociclização dos alquenil-β-enaminoésteres 7, 8, 9 e 10, respectivamente, com modificações na metodologia. Os tempos de reação foram diminuídos e o método de purificação foi modificado. Visando à extensão da metodologia para a obtenção de heterociclos nitrogenados de 6 membros, foi testada a iodociclização dos alquenil-S-enaminoésteres 11 e 12. O composto 11 forneceu o produto esperado 17 em 51% de rendimento enquanto que o composto 12 não sofreu ciclização nestas condições, porém ao modificá-las foi obtido composto 18', via lactonização.As reações de desidroalogenação dos compostos 13, 14, 15 e 16 levaram aos produtos esperados 19, 20, 21 e 22, com rendimentos de 93, 99, 75 e 93%, respectivamente. O composto 17 não gerou nenhum produto nestas condições, mas ao modificá-las obteve-se o composto 23', resultante de substituição nucleofilica interna, com 79% de rendimento. Nestas condições, os compostos 15 e 16 sofreram eliminação de HI gerando os compostos 21' e 22', respectivamente.
Title in English
Studies about iodocyclization and dehydroiodation and N-benzyl-beta- enaminoesthers (OU) Studies about iodocyclization and dehydroiodation of -enaminoesthers
Keywords in English
Chemical reactions
Nitrogen compounds
Oxygen compounds
Physical chemistry organic
Abstract in English
Cyclic iodo-β-enaminoesthers 13, 14, 15 e 16 (five-membered nitrogen heterocycles) were prepared by iodocyc1ization of alkenyl-β-enaminoesthers 7, 8, 9 e 10, respectively, with modifications in the method. The reaction times were diminished and the method of purification was changed. In order to extend this metodology to obtain six-membered nitrogen heterocycles, the iodocyclization of the alkenyl-β enaminoesthers 11 and 12 was tested. Compound 11 furnished the expected product 17 in 51% yield while compound 12 did not undergo cyclization in such conditions, however by changing them compound 18' was obtained, via lactonization. The dehalogenation reaction of compounds 13, 14, 15 and 16 afforded the expected products 19, 20, 21 and 22, in 93, 99, 75 and 93% yield, respectively. Compound 17 did not furnish any products in these conditions, but modifying them compoud 23' was obtained, resulting from a internal nucleophilic substitution, in 79% yield. In these conditions, compounds 15 and 16 underwent HI elimination giving compounds 21' e 22', respectively.
 
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Publishing Date
2015-11-18
 
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