A carregar...
Publicação
Pd-catalyzed domino synthesis of heterocycles
| Nome: | Descrição: | Tamanho: | Formato: | |
|---|---|---|---|---|
| 1.65 MB | Adobe PDF |
Orientador(es)
Resumo(s)
Foram sintetizados compostos do tipo indole e benzodihidrofuranos, por recurso à catálise com complexos de paládio. Procurou construir-se uma reacção dominó com vista a incorporar uma etapa de allilação decarboxilativa, quer por inserção de CO na presença de ácool alilíco, quer utilizando um substrato já com um éster alílico na posição desejada. A alilação do grupo metino do indole malónico foi também explorada, por simples substituição nucleófila ou com activação do substrato alílico com Pd. A contrução de benzodihidrofuranos, passou numa primeira etapa pela obtenção do iodo-éter capaz de sofrer carbopaladação. Seguiu-se uma metodologia de reactor único identica à do caso dos heterociclos azotados numa primeira etapa para procurar aprisionamento nucleófilo com hidreto, e numa segunda metoxicarbonilação.
Indole and benzodihydrofurane type compounds were synthetized by using palladium catalysis. A domino reaction was constructing looking forward to incorporate a decarboxylative allylation step, either by CO insertion in the presence of allylic alcohol, either byusing a substrate already containing the appropriate allylic ester moiety. Allylation of the indole malonic methine group was also explored, by simple nucleophilic substitution or activation of the allylic substrate with Pd. The construction of benzodihydrofuranes underwent in an early stage the synthesis of the iodo-ether substrate to undergo carbopalladation. A one-pot methodology akin to the one used for the nitrogen heterocycles was used in a first time seeking to perform a nucleophilic trapping with hydride and secondly methoxycarbonilation.
Indole and benzodihydrofurane type compounds were synthetized by using palladium catalysis. A domino reaction was constructing looking forward to incorporate a decarboxylative allylation step, either by CO insertion in the presence of allylic alcohol, either byusing a substrate already containing the appropriate allylic ester moiety. Allylation of the indole malonic methine group was also explored, by simple nucleophilic substitution or activation of the allylic substrate with Pd. The construction of benzodihydrofuranes underwent in an early stage the synthesis of the iodo-ether substrate to undergo carbopalladation. A one-pot methodology akin to the one used for the nitrogen heterocycles was used in a first time seeking to perform a nucleophilic trapping with hydride and secondly methoxycarbonilation.
Descrição
Tese de mestrado em Química, apresentada à Universidade de Lisboa, através da Faculdade de Ciências, 2013
Palavras-chave
Catálise Paládio CO Dominó Heterociclos Teses de mestrado - 2013