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|All Authors / Contributors:||
Damien Bonne; Jieping Zhu; Université de Paris-Sud. Faculté des Sciences d'Orsay (Essonne).; Université de Paris-Sud.
|Notes:||Thèse rédigée en français et en anglais.|
|Description:||1 vol. (286 p.) ; 30 cm.|
|Responsibility:||Damien Bonne ; sous la direction de [Jieping Zhu].|
We have shown that potassium isocyano acetic acid derivatives can efficiently participate in Ugi 4CR/five centers reaction leading to the formation of dipeptides or tripeptides. We have also developed a novel method for oxidative homologation of aldehyde to amide using the same isocyano acetic acid derivative. The reaction is realized under very mild conditions using readily accessible reagents. While multicomponent reaction (MCR) is gaining popularity for creating the structural complexity and diversity, we demonstrated herein that research on MCR can also lead to the discovery of new fundamental transformations.The difference in the reaction pathway using isocyanoacetic acid derivatives is essentially based on the substitution (alkyl or aryl) in the alpha position of the isonitrile.We also work in the development of two new multicomponent reactions:A four-component sythesis of furopyrrolones based on the unique reactivity of an isocyanoacetate bearing a 4-nitrophenyl group in the alpha position..A three-component synthesis of 4-imino-4H-3,1-benzoxazines exploiting the dual reactivity of 2-isocyanobenzamide derivatives.The work we have done show the power and potential of isocyanide-based multicomponent reactions (IMCRs). It is important to say that the chemistry we have been dealt with is also very subtle: the isonitriles employed in the three first chapters have very similar structures but the scaffolds accessible by the MCRs we developed are completely different.The four processes we developed during the last three years are quite efficient in terms of yield and simplicity of operation. They are therefore very useful tools for synthetic chemists.