A cascade A<sup>3</sup> coupling strategy towards the regioselective synthesis of β-carboline <i>N</i>-fused pyrrole derivatives with pyridine tethers

The alkali metal tert‐butoxides have found wide application as catalysts and activators for the conversion of numerous organic molecules. These formidable additives in catalytic amounts are extensively employed in the transition metal‐free approaches to serve for the single‐electron transfer processes towards the formation of C−C and C‐heteroatom bond formation. This review elucidates their multifaceted roles encompassing a series of novel synthetic methodologies, in‐depth analyses of their reactivity patterns, and catalytic efficiencies across a myriad of reactions. The involvement of alkali metal tert‐butoxides either directly or in combination with other metals as catalysts are discussed along with the detailed mechanistic pathways in various reactions. Overall, this article summarises approximately all reactions those have been influenced by the catalytic amounts of tert‐butoxides and reported in the last decades.

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Roles of Alkali Metals tert‐Butoxide as Catalysts and Activators in Organic Transformations

Patel

Banerjee

Kant

et al. 2023

Asian J Org Chem

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Transition Metal‐Free Diastereoselective Synthesis of β‐Carboline Tethered Dihydrofurocoumarin Derivatives

Banyal,

Malakar,

Kumar

et al. 2024

Asian J Org Chem

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One‐pot procedure has been developed for the synthesis of novel β‐carboline tethered trans 2,3‐furocoumarins via assembling 1‐formyl‐β‐carbolines, 4‐hydroxycoumarins, and phenacyl bromides in pyridine under transition metal‐free conditions. The strategy was also found applicable to gram scale synthesis and a library of 40 molecules has been developed. The significant features of this operationally facile approach includes high efficiency, short reaction time, excellent yields, multicomponent character of the reaction, metal‐free mild reaction conditions, and a column chromatography free purification procedure.

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DIPEA‐Assisted Efficient One‐Pot Three‐Component Synthesis of Novel β‐Carboline Tethered Pyran Derivatives

Banyal,

Malakar,

Kumar

et al. 2024

ChemistrySelect

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A potential DIPEA‐assisted approach has been unfolded for the synthesis of novel β‐carboline tethered‐4H‐pyran derivatives via one‐pot condensation of 1‐formyl‐9H‐β‐carbolines, β‐keto esters and malononitrile in ethanol at ambient temperature. A library of 28 new β‐carboline tethered 4H‐pyran derivatives has been developed. The significant features of the present strategy include high efficiency, excellent yield, inexpensive catalyst, mild reaction conditions, multicomponent character of reaction and simple purification procedure.

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A cascade A³ coupling strategy towards the regioselective synthesis of β-carboline N-fused pyrrole derivatives with pyridine tethers

Abstract: A potential three component reaction strategy has been devised to generate the nature inspired β-carboline N-fused pyrroles containing pyridine tethers. These scaffolds were afforded in high yields via one-pot cascade...

Cited by 6 publications

References 68 publications

Roles of Alkali Metals tert‐Butoxide as Catalysts and Activators in Organic Transformations

Roles of Alkali Metals tert‐Butoxide as Catalysts and Activators in Organic Transformations

Transition Metal‐Free Diastereoselective Synthesis of β‐Carboline Tethered Dihydrofurocoumarin Derivatives

DIPEA‐Assisted Efficient One‐Pot Three‐Component Synthesis of Novel β‐Carboline Tethered Pyran Derivatives

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A cascade A3 coupling strategy towards the regioselective synthesis of β-carboline N-fused pyrrole derivatives with pyridine tethers

Abstract: A potential three component reaction strategy has been devised to generate the nature inspired β-carboline N-fused pyrroles containing pyridine tethers. These scaffolds were afforded in high yields via one-pot cascade...

Cited by 6 publications

References 68 publications

Roles of Alkali Metals tert‐Butoxide as Catalysts and Activators in Organic Transformations

Roles of Alkali Metals tert‐Butoxide as Catalysts and Activators in Organic Transformations

Transition Metal‐Free Diastereoselective Synthesis of β‐Carboline Tethered Dihydrofurocoumarin Derivatives

DIPEA‐Assisted Efficient One‐Pot Three‐Component Synthesis of Novel β‐Carboline Tethered Pyran Derivatives

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Product

Resources

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A cascade A³ coupling strategy towards the regioselective synthesis of β-carboline N-fused pyrrole derivatives with pyridine tethers