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Proceeding Paper

MW-Assisted Synthesis of Eight New 6-Nitrilmethyl Pyrrolo[3,4-b]pyridin-5-Ones via a Domino Process: aza Diels–Alder/N-Acylation/Aromatization †

by
Manuel A. Rentería-Gómez
1,
Shrikant G. Pharande
1,
Alejandro Islas-Jácome
2,*,
Eduardo González-Zamora
2,* and
Rocío Gámez-Montaño
1,*
1
Departamento de Química, Universidad de Guanajuato, Noria Alta S/N, Col. Noria Alta, Guanajuato C.P. 36050, Gto., Mexico
2
Departamento de Química, Universidad Autónoma Metropolitana-Iztapalapa, San Rafael Atlixco 186, Col. Vicentina, Iztapalapa C.P. 09340, Mexico
*
Authors to whom correspondence should be addressed.
†
Presented at the 22nd International Electronic Conference on Synthetic Organic Chemistry, 15 November– 15 December 2018; Available Online: https://sciforum.net/conference/ecsoc-22.
Proceedings 2019, 9(1), 5; https://doi.org/10.3390/ecsoc-22-05779
Published: 14 November 2018
(This article belongs to the Proceedings of 22nd International Electronic Conference on Synthetic Organic Chemistry)
Versions Notes

Abstract

An efficient Microwave (MW)-assisted synthesis of eight new 6-nitrilmethyl-pyrrolo[3,4-b]pyridin-5-ones via a domino process: aza Diels–Alder/N-acylation/aromatization (dehydration–decarboxylation) from their corresponding 2-aminonitrile-oxazoles and maleic anhydride are described. The use of MW as a heat source and scandium (III) triflate as a catalyst to promote the cycloaddition process was crucial to construct these polyfunctionalized products in very good yields (51–79%), considering both their molecular complexity and that only one domino-type experimental procedure was required for their synthesis. It is worth noting that all products reported herein have not been synthesized nor isolated anywhere. However, they can be of high interest for the synthetic and medicinal chemistry community because pyrrolo[3,4-b]pyridin-5-one is the structural core of various bioactive compounds. In the same context, it can be considered as a privileged aza analogue of the isoindolin-1-one, which in turn is the core of numerous anticancer agents.
Keywords: multicomponent reactions; Ugi-three-component reactions; pyrrolo[3,4-b]pyridin-5-ones; domino processes; aza Diels–Alder cycloadditions; N-acylations; aromatization processes multicomponent reactions; Ugi-three-component reactions; pyrrolo[3,4-b]pyridin-5-ones; domino processes; aza Diels–Alder cycloadditions; N-acylations; aromatization processes

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MDPI and ACS Style

Rentería-Gómez, M.A.; Pharande, S.G.; Islas-Jácome, A.; González-Zamora, E.; Gámez-Montaño, R. MW-Assisted Synthesis of Eight New 6-Nitrilmethyl Pyrrolo[3,4-b]pyridin-5-Ones via a Domino Process: aza Diels–Alder/N-Acylation/Aromatization. Proceedings 2019, 9, 5. https://doi.org/10.3390/ecsoc-22-05779

AMA Style

Rentería-Gómez MA, Pharande SG, Islas-Jácome A, González-Zamora E, Gámez-Montaño R. MW-Assisted Synthesis of Eight New 6-Nitrilmethyl Pyrrolo[3,4-b]pyridin-5-Ones via a Domino Process: aza Diels–Alder/N-Acylation/Aromatization. Proceedings. 2019; 9(1):5. https://doi.org/10.3390/ecsoc-22-05779

Chicago/Turabian Style

Rentería-Gómez, Manuel A., Shrikant G. Pharande, Alejandro Islas-Jácome, Eduardo González-Zamora, and Rocío Gámez-Montaño. 2019. "MW-Assisted Synthesis of Eight New 6-Nitrilmethyl Pyrrolo[3,4-b]pyridin-5-Ones via a Domino Process: aza Diels–Alder/N-Acylation/Aromatization" Proceedings 9, no. 1: 5. https://doi.org/10.3390/ecsoc-22-05779

APA Style

Rentería-Gómez, M. A., Pharande, S. G., Islas-Jácome, A., González-Zamora, E., & Gámez-Montaño, R. (2019). MW-Assisted Synthesis of Eight New 6-Nitrilmethyl Pyrrolo[3,4-b]pyridin-5-Ones via a Domino Process: aza Diels–Alder/N-Acylation/Aromatization. Proceedings, 9(1), 5. https://doi.org/10.3390/ecsoc-22-05779

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