Calix[n]arene-catalysed three-component Povarov reaction: microwave-assisted synthesis of julolidines and mechanistic insights
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2018
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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.
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ABRANCHES, Paula Aline da Silva et al. Calix[n]arene-catalysed three-component Povarov reaction: microwave-assisted synthesis of julolidines and mechanistic insight. The Journal of Organic Chemistry, Washington, v. 83, n. 4, p. 1761-1771, 2018. DOI: 10.1021/acs.joc.7b02532. Disponível em: https://pubs.acs.org/doi/10.1021/acs.joc.7b02532. Acesso em: 28 nov. 2023.