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Synthesis of Polyheterocyclic Pyrrolo[3,4-b]pyridin-5-ones via a One-Pot (Ugi-3CR/aza Diels-Alder/N-acylation/aromatization/SN2) Process. A Suitable Alternative towards Novel Aza-Analogues of Falipamil

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Unidad Profesional Interdisciplinaria de Biotecnología, Instituto Politécnico Nacional, Av. Acueducto de Guadalupe S/N, Barr. La Laguna Ticomán, C.P. 07340, Del. Gustavo A Madero, Ciudad de México, Mexico
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Departamento de Química, Universidad Autónoma Metropolitana-Iztapalapa, San Rafael Atlixco 186, Col. Vicentina, C.P. 09340, Del. Iztapalapa, Ciudad de México, Mexico
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Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional, Prol. Manuel Carpio y Plan de Ayala S/N, Col. Santo Tomás, C.P. 11340, Del. Miguel Hidalgo, Ciudad de México, Mexico
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Laboratorio de Fisicoquímica y Reactividad de Superficies, Instituto de Investigaciones en Materiales, Universidad Nacional Autónoma de México, Circuito Exterior S/N, Ciudad Universitaria, C.P. 04510, Del. Coyoacán, Ciudad de México, Mexico
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Authors to whom correspondence should be addressed.
Molecules 2018, 23(4), 763; https://doi.org/10.3390/molecules23040763
Received: 20 February 2018 / Revised: 16 March 2018 / Accepted: 23 March 2018 / Published: 27 March 2018
(This article belongs to the Section Organic Chemistry)
We describe the one-pot synthesis of twenty polyheterocyclic pyrrolo[3,4-b]pyridin-5-ones via a cascade process (Ugi-3CR/aza Diels-Alder/N-acylation/aromatization) in 20 to 95% overall yields, as well as four pharmacologically promising analogues via an improved cascade process (Ugi-3CR/aza Diels-Alder/N-acylation/aromatization/SN2): two piperazine-linked pyrrolo[3,4-b]pyridin-5-ones in 33 and 34%, and a couple of Falipamil aza-analogues in 30 and 35% overall yields. It is worth highlighting the good substrate scope found, because final products are furnished with alkyl, aryl, and heterocyclic substituents. The use of chain-ring tautomerizable isocyanides (as key reagents for the Ugi-type three component reaction) allowed for a rapid and efficient assembly of the polysubstituted oxindoles, which were used in situ toward the complex products, conferring features like robustness, sustainability, and the one-pot approach to this synthetic methodology. View Full-Text
Keywords: one-pot procedures; cascade processes; multicomponent reactions; Ugi-3CR; aza Diels-Alder Cycloadditions; microwave assisted synthesis; Pyrrolo[3,4-b]pyridin-5-ones; Falipamil; piperazine-linker one-pot procedures; cascade processes; multicomponent reactions; Ugi-3CR; aza Diels-Alder Cycloadditions; microwave assisted synthesis; Pyrrolo[3,4-b]pyridin-5-ones; Falipamil; piperazine-linker
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MDPI and ACS Style

Zamudio-Medina, A.; García-González, A.N.; Herrera-Carrillo, G.K.; Zárate-Zárate, D.; Benavides-Macías, A.; Tamariz, J.; Ibarra, I.A.; Islas-Jácome, A.; González-Zamora, E. Synthesis of Polyheterocyclic Pyrrolo[3,4-b]pyridin-5-ones via a One-Pot (Ugi-3CR/aza Diels-Alder/N-acylation/aromatization/SN2) Process. A Suitable Alternative towards Novel Aza-Analogues of Falipamil. Molecules 2018, 23, 763. https://doi.org/10.3390/molecules23040763

AMA Style

Zamudio-Medina A, García-González AN, Herrera-Carrillo GK, Zárate-Zárate D, Benavides-Macías A, Tamariz J, Ibarra IA, Islas-Jácome A, González-Zamora E. Synthesis of Polyheterocyclic Pyrrolo[3,4-b]pyridin-5-ones via a One-Pot (Ugi-3CR/aza Diels-Alder/N-acylation/aromatization/SN2) Process. A Suitable Alternative towards Novel Aza-Analogues of Falipamil. Molecules. 2018; 23(4):763. https://doi.org/10.3390/molecules23040763

Chicago/Turabian Style

Zamudio-Medina, Angel; García-González, Ailyn N.; Herrera-Carrillo, Genesis K.; Zárate-Zárate, Daniel; Benavides-Macías, Adriana; Tamariz, Joaquín; Ibarra, Ilich A.; Islas-Jácome, Alejandro; González-Zamora, Eduardo. 2018. "Synthesis of Polyheterocyclic Pyrrolo[3,4-b]pyridin-5-ones via a One-Pot (Ugi-3CR/aza Diels-Alder/N-acylation/aromatization/SN2) Process. A Suitable Alternative towards Novel Aza-Analogues of Falipamil" Molecules 23, no. 4: 763. https://doi.org/10.3390/molecules23040763

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