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http://hdl.handle.net/1843/76459| Type: | Artigo de Periódico |
| Title: | A calix[n]arene-catalysed three-component povarov reaction: microwave-assisted synthesis of julolidines and mechanistic insights |
| Authors: | Paula Aline da Silva Abranches Walysson Ferreira de Paiva Ângelo de Fátima Felipe Terra Martins Sergio Antonio Fernandes |
| Abstract: | 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. |
| Subject: | Calixarenos Compostos heterocíclicos Aldeídos Catalisadores Reações químicas Ions Reações de substituição |
| language: | eng |
| metadata.dc.publisher.country: | Brasil |
| Publisher: | Universidade Federal de Minas Gerais |
| Publisher Initials: | UFMG |
| metadata.dc.publisher.department: | ICX - DEPARTAMENTO DE QUÍMICA |
| Rights: | Acesso Restrito |
| metadata.dc.identifier.doi: | https://doi.org/10.1021/acs.joc.7b02532 |
| URI: | http://hdl.handle.net/1843/76459 |
| Issue Date: | 2018 |
| metadata.dc.url.externa: | https://pubs.acs.org/doi/10.1021/acs.joc.7b02532?src=getftr# |
| metadata.dc.relation.ispartof: | The Journal of Organic Chemistry |
| Appears in Collections: | Artigo de Periódico |
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