Piperidine-Iodine as Efficient Dual Catalyst for the One-Pot, Three-Component Synthesis of Coumarin-3-Carboxamides

Velasco, Manuel; Romero-Ceronio, Nancy; Torralba, Rosalía; Abreu, Oswaldo Hernández; Vilchis‐Reyes, Miguel A.; Alarcón-Matus, Erika; Ramos-Rivera, Erika M.; Aparicio, David M.; Jiménez, Jacqueline; García, E. Aguilar; Cruz, David Cruz; Gómez, Clarisa Villegas; Alvarado, Cuauhtémoc

doi:10.3390/molecules27144659

Cited by 3 publications

(1 citation statement)

References 45 publications

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“…Velasco and co‐workers [121] reported the reaction of salicylaldehydes, aliphatic primary/secondary amines and diethylmalonate using piperidine‐iodine as dual catalyst to yield coumarin‐3‐carboxamide derivatives 123 (Scheme 61).…”

Section: Iodine Catalyzed/mediated Multi‐component Reactionsmentioning

confidence: 99%

A Review on Molecular Iodine Catalyzed/Mediated Multicomponent Reactions

et al. 2022

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In multicomponent reactions, three or more reactants combine in one pot to form a product without the isolation of intermediate and most of the reactants contribute to newly formed product reducing number of steps involved and waste generated. Molecular iodine is mild, efficient, relatively nontoxic, inexpensive, commercially available, and catalyzes various organic reactions due to its Lewis acidic behaviour. The development of multicomponent reactions catalyzed by molecular iodine indeed is a good green alternative for synthetic organic chemistry. The aim of this article is to review all important multicomponent reactions catalyzed by molecular iodine reported since 2013 in order to envisage some new efficient protocols for the synthesis of structurally complex molecules.

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Section: Iodine Catalyzed/mediated Multi‐component Reactionsmentioning

confidence: 99%

A Review on Molecular Iodine Catalyzed/Mediated Multicomponent Reactions

et al. 2022

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Six-membered ring systems: With O and/or S atoms

Santos,

Silva

2023

Progress in Heterocyclic Chemistry

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An ultrasound assisted, ionic liquid-molecular iodine synergy driven efficient green synthesis of pyrrolobenzodiazepine-triazole hybrids as potential anticancer agents

et al. 2023

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Herein, we report an efficient and eco-friendly, ultrasound assisted synthetic strategy for the construction of diversified pyrrolobenzodiazepine-triazole hybrids, which are potentially pharmaceutically important scaffolds, via a domino reaction involving intermolecular electrophilic substitution followed by intramolecular Huisgen 1,3-dipolar azide-alkyne cycloaddition. The USP of the reported protocol is the use of benign and inexpensive, recyclable molecular iodine-ionic liquid synergistic catalytic system cum reaction media for achieving the synthesis. The other salient features of this method are the use of mild reaction conditions, high yield and atom economy, operational simplicity, broad substrate scope and easy workup and purification. All the synthesized compounds were evaluated for in vitro anti-proliferative activity against various cancer cell lines. From among the synthesized title compounds, 9,9-dimethyl-8-phenyl-9H-benzo [b]pyrrolo [1,2-d][1,2,3]triazolo[5,1-g][1,4]diazepine (7) was found most to be the most active compound exhibiting IC50 value of 6.60, 5.45, 7.85, 11.21, 12.24, 10.12, and 11.32 µM against MCF-7, MDA-MB-231, HeLa, SKOV-3, A549, HCT-116 and DLD-1 cell lines, respectively. Further the compounds were found to be non-toxic against normal human embryonic kidney (HEK-293) cell line.

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Piperidine-Iodine as Efficient Dual Catalyst for the One-Pot, Three-Component Synthesis of Coumarin-3-Carboxamides

Cited by 3 publications

References 45 publications

A Review on Molecular Iodine Catalyzed/Mediated Multicomponent Reactions

A Review on Molecular Iodine Catalyzed/Mediated Multicomponent Reactions

Six-membered ring systems: With O and/or S atoms

An ultrasound assisted, ionic liquid-molecular iodine synergy driven efficient green synthesis of pyrrolobenzodiazepine-triazole hybrids as potential anticancer agents

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