A multicomponent coupling reaction (MCR) is a powerful transformation, combining three or more starting materials to form several new bonds in a one-pot process that efficiently affords highly functionalized molecular scaffolds. The Passerini-Smiles reaction is an isocyanide-based multicomponent coupling reaction (IMCR) that combines an electron-deficient phenol, aldehyde, and isocyanide to produce an α-acyloxy amide. Reactions like this provide methods to construct diverse families of compounds, and are useful for the synthesis of biologically-relevant complex molecules.
Herein we report the discovery of novel, Passerini-Smiles acyl adduct isomers when furaldehyde derivatives are used as a reaction component. Our goals focus on evaluation of the functional group tolerance for this reaction, and gaining a better understanding of the reaction scope and mechanism. Application of allyl-substituted nitrophenols in the Passerini Smiles reaction provides rearranged acyl adducts. This reaction was further developed through optimization studies and functional group variation.
|Commitee:||Dixon, Robert, Miller, Lynne, Wei, Chin-Chuan|
|School:||Southern Illinois University at Edwardsville|
|School Location:||United States -- Illinois|
|Source:||MAI 55/05M(E), Masters Abstracts International|
|Keywords:||Allyl substituted nitrophenols, Aryl adducts, Isocyanide-based multicomponent coupling reaction, Passerini-smiles|
Copyright in each Dissertation and Thesis is retained by the author. All Rights Reserved
The supplemental file or files you are about to download were provided to ProQuest by the author as part of a
dissertation or thesis. The supplemental files are provided "AS IS" without warranty. ProQuest is not responsible for the
content, format or impact on the supplemental file(s) on our system. in some cases, the file type may be unknown or
may be a .exe file. We recommend caution as you open such files.
Copyright of the original materials contained in the supplemental file is retained by the author and your access to the
supplemental files is subject to the ProQuest Terms and Conditions of use.
Depending on the size of the file(s) you are downloading, the system may take some time to download them. Please be