Calix[n]arene-Catalyzed Three-Component Povarov Reaction: Microwave-Assisted Synthesis of Julolidines and Mechanistic Insights
| Autor: | Felipe T. Martins, Sergio Antonio Fernandes, Walysson Ferreira de Paiva, Paula Aline da Silva Abranches, Ângelo de Fátima |
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| Rok vydání: | 2018 |
| Předmět: |
010405 organic chemistry
Component (thermodynamics) Povarov reaction Organic Chemistry Ionic bonding 010402 general chemistry 01 natural sciences Microwave assisted Combinatorial chemistry 0104 chemical sciences Catalysis Calix[n]arene-catalyzed chemistry.chemical_compound Cascade reaction chemistry Julolidine |
| Zdroj: | LOCUS Repositório Institucional da UFV Universidade Federal de Viçosa (UFV) instacron:UFV |
| ISSN: | 1520-6904 |
| Popis: | A new one-pot cascade reaction-based application of Povarov reactions with a p-sulfonic acid calix[4]arene catalyst for the synthesis of a series of 34 julolidine derivatives with substituents at C8 or C9 in good to excellent yields is reported. These microwave-assisted reactions proceeded efficiently, had short reaction times, were metal-free, were low cost, and used an inexpensive, easily available and nontoxic catalyst. These advantages, along with a simple workup procedure, make this protocol a very efficient and green alternative to the traditional methods for constructing these types of N- heterocyclic skeletons. In addition, this protocol allows the formation of julolidine structures, which requires the construction of four new C−C bonds and two C−N bonds. A mechanism for the Povarov reaction involving a stepwise sequence via ionic intermediates was proposed and validated. |
| Databáze: | OpenAIRE |
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