Calixarene Catalyze Cascade Povarov−Hydrogen-Transfer Reaction in Synthesis of Quinolines

Calixarene Catalyze Cascade Povarov−Hydrogen-Transfer Reaction in Synthesis of Quinolines

Simões, Juliana B.; Fátima, Ângelo de; Barbosa, Luiz Claudio A.; Fernandes, Sergio A.

Abstract:

Quinoline nucleus is a common heterocyclic ring found in natural and unnatural compounds endowed with biological properties. Tetrahydroquinolines are easily obtained from Povarov reaction which correspond to the reaction of arylimines with electron-rich olefins. Further, the obtained tetrahydroquinolines may be further transformed into quinolines by oxidantion. Indeed, Povarov reaction followed by an oxidative aromatization, in a cascade process, was reported using excess of arylimine as oxidant (Fig. 1). The p-sulfonic acid calix[4]arene (CX4SO3H) has been employed as catalysts in Povarov reaction for synthesis of julolidines. Here we employ CX4SO3H as a catalyst for synthesis of substituted quinolines.

Quinoline nucleus is a common heterocyclic ring found in natural and unnatural compounds endowed with biological properties. Tetrahydroquinolines are easily obtained from Povarov reaction which correspond to the reaction of arylimines with electron-rich olefins. Further, the obtained tetrahydroquinolines may be further transformed into quinolines by oxidantion. Indeed, Povarov reaction followed by an oxidative aromatization, in a cascade process, was reported using excess of arylimine as oxidant (Fig. 1). The p-sulfonic acid calix[4]arene (CX4SO3H) has been employed as catalysts in Povarov reaction for synthesis of julolidines. Here we employ CX4SO3H as a catalyst for synthesis of substituted quinolines.

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DOI: 10.5151/chempro-15bmos-BMOS2013_2013915211651

Referências bibliográficas

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Como citar:

Simões, Juliana B.; Fátima, Ângelo de; Barbosa, Luiz Claudio A.; Fernandes, Sergio A.; "Calixarene Catalyze Cascade Povarov−Hydrogen-Transfer Reaction in Synthesis of Quinolines", p-275-275. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-15bmos-BMOS2013_2013915211651