Synthesis of 5 <i>H</i> -Pyrrolo[3,4- <i>b</i> ]Pyridin-5-Ones <i>via</i> a Cerium Chloride Catalyzed Multicomponent Cascade Process: A One-Pot Approach Incorporating Ugi-Zhu 3CR, Aza Diels–Alder, <i>N</i> -Acylation, and Aromatization Reactions

We have synthesized <i>α</i>-isocyano-<i>β</i>-phenylpropionamides 5 (a–c) using a two-step process and then created a new series of poly-substituted 5<i>H</i>-pyrrolo[3,4-<i>b</i>]pyridin-5-ones 12 (a–o) <i>via</i> a multi-component reaction. Most of the reported literature used scandium triflate and either benzene or toluene as solvents, which are not good for the environment. We have identified cerium(III) chloride as the catalyst and acetonitrile as the solvent for conversion, which is harmless to the environment. The synthetic strategy involved Ugi-Zhu 3CR (UZ-3CR), Aza Diels–Alder, <i>N</i>-acylation, and aromatization steps, yielding products in the range of 65–85%.

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Journal
Polycyclic aromatic compounds
Published
2024-12-03
DOI
https://doi.org/10.1080/10406638.2024.2434570
Primary Topic
Multicomponent Synthesis of Heterocycles
Type
article
Field-Weighted Citation Impact
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article

Synthesis of 5 H -Pyrrolo[3,4- b ]Pyridin-5-Ones via a Cerium Chloride Catalyzed Multicomponent Cascade Process: A One-Pot Approach Incorporating Ugi-Zhu 3CR, Aza Diels–Alder, N -Acylation, and Aromatization Reactions

M. B. Madhusudana Reddy, Duraisamy Ramasamy, I.V. Asharani, D. Thirumalai
Polycyclic aromatic compounds
Multicomponent Synthesis of Heterocycles
article

Synthesis of 5 H -Pyrrolo[3,4- b ]Pyridin-5-Ones via a Cerium Chloride Catalyzed Multicomponent Cascade Process: A One-Pot Approach Incorporating Ugi-Zhu 3CR, Aza Diels–Alder, N -Acylation, and Aromatization Reactions

M. B. Madhusudana Reddy, Duraisamy Ramasamy, I.V. Asharani, D. Thirumalai
article en

Abstract

We have synthesized <i>α</i>-isocyano-<i>β</i>-phenylpropionamides 5 (a–c) using a two-step process and then created a new series of poly-substituted 5<i>H</i>-pyrrolo[3,4-<i>b</i>]pyridin-5-ones 12 (a–o) <i>via</i> a multi-component reaction. Most of the reported literature used scandium triflate and either benzene or toluene as solvents, which are not good for the environment. We have identified cerium(III) chloride as the catalyst and acetonitrile as the solvent for conversion, which is harmless to the environment. The synthetic strategy involved Ugi-Zhu 3CR (UZ-3CR), Aza Diels–Alder, <i>N</i>-acylation, and aromatization steps, yielding products in the range of 65–85%.

Polycyclic aromatic compoundsVol. 45(6)
Thiruvalluvar University (IN), REVA University (IN), Vellore Institute of Technology University (IN)
Tamil Nadu State Council for Higher Education
Openalex Percentile: Top 84%
Multicomponent Synthesis of Heterocycles
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