Povarov reaction for the synthesis of 2-(2-pyridyl)quinoline

Povarov reaction for the synthesis of 2-(2-pyridyl)quinoline

Barbosa, Luiz C. A.; Borel, Carmindo R.; Fernandes, Sergio A.; Maltha, Célia R. A.

Abstract:

Antitumor antibiotic streptonigrin (1) is an highly functionalized quinolinequinone which has attracted considerable attention from synthetic organic chemistry and biochemists, due to its antitumor activity. Thus, considerable efforts have been made to obtain analogues of streptonigrin, with the ultimate goal to obtain a molecule with promising anticancer activity and attenuated toxicity. Multicomponent reactions (MCRs) continue to attract attention as they can result in a substantial increase in molecular complexity and provide opportunities for high levels of convergence in synthesis. The use of MCRs has therefore been frequently adopted by the pharmaceutical industry for the development of combinatorial libraries and the identification of lead compounds. In this work we investigate the synthesis of 2- pyridylquinolines via MCR cascade process known as the Povarov reaction. The aim was to develop an efficient protocol for the preparation 2- pyridylquinolines that constitutes the core structure of streptonigrin, and then apply this methodology to prepare several analogues for biological evaluation.

Antitumor antibiotic streptonigrin (1) is an highly functionalized quinolinequinone which has attracted considerable attention from synthetic organic chemistry and biochemists, due to its antitumor activity. Thus, considerable efforts have been made to obtain analogues of streptonigrin, with the ultimate goal to obtain a molecule with promising anticancer activity and attenuated toxicity. Multicomponent reactions (MCRs) continue to attract attention as they can result in a substantial increase in molecular complexity and provide opportunities for high levels of convergence in synthesis. The use of MCRs has therefore been frequently adopted by the pharmaceutical industry for the development of combinatorial libraries and the identification of lead compounds. In this work we investigate the synthesis of 2- pyridylquinolines via MCR cascade process known as the Povarov reaction. The aim was to develop an efficient protocol for the preparation 2- pyridylquinolines that constitutes the core structure of streptonigrin, and then apply this methodology to prepare several analogues for biological evaluation.

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DOI: 10.5151/chempro-15bmos-BMOS2013_2013816161848

Referências bibliográficas

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Como citar:

Barbosa, Luiz C. A.; Borel, Carmindo R.; Fernandes, Sergio A.; Maltha, Célia R. A.; "Povarov reaction for the synthesis of 2-(2-pyridyl)quinoline", p-158-158. 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_2013816161848