Recent Advances in the Synthesis
of Pyridines by Transition-Metal-Catalyzed [2+2+2] Cycloaddition

Varela, Jesús A.; Saá, Carlos

doi:10.1055/s-2008-1078275

Cited by 43 publications

(1 citation statement)

References 10 publications

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“… Therefore, the synthesis of substituted pyridines has been actively pursued to date. To access diverse substitution patterns, many affective and regioselective syntheses using simple substrates have been established, most of which are based upon condensation reactions of carbonyl compounds, cycloaddition reactions, organocatalytic reactions, or via miscellaneous procedures, such as ring expansion or the intramolecular cyclization process of specific pre-synthesized starting materials (Figure S1).…”

Section: Introductionmentioning

confidence: 99%

One-Pot Synthetic Approach to 3-Carboxyl- and 3-Ketopyridines in Aqueous Media

Bena,

Bakalbassis,

Sigalas

et al. 2023

J. Org. Chem.

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We describe a one-pot strategy to access 3-carboxyland 3-ketopyridines from readily available alkynes and propargylamine via a hydroamination process. This one-pot protocol uses alkynes as starting materials, has a broad substrate scope, and operates in aqueous media and open-air conditions. A series of aryland alkyl-substituted pyridines were synthesized. This green methodology can be scaled to laboratory size and was used for the synthesis of the natural product core, 4-aza-fluorenone. Density-functional theory and control mechanistic studies support a domino hydroamination/pericyclic reaction, which includes the formation of the enaminone intermediate and its transformation through an aza-Claisen rearrangement to the desired pyridine product.

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Section: Introductionmentioning

confidence: 99%

One-Pot Synthetic Approach to 3-Carboxyl- and 3-Ketopyridines in Aqueous Media

Bena,

Bakalbassis,

Sigalas

et al. 2023

J. Org. Chem.

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[2+2+2] Cycloadditions of Alkynes with Heterocumulenes and Nitriles

2019

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[2+2+2] Cycloadditions of heterocumulenes and nitriles represent an efficient, atom‐economical method of synthesizing heterocycles and, to a lesser extent, carbocycles. Cycloadditions of heterocumulenes including isocyanates, carbodiimides, carbon dioxide, carbon disulfide, ketenes, as well as nitriles are explored. The heterocumulene is typically coupled with an alkyne or diyne, forming 6‐membered heterocycles, although multiple heterocumulenes are sometimes incorporated. The reactions are generally catalyzed by late‐transition‐metal catalysts, albeit nucleophilic catalysts and early‐transition metals are sometimes used. [2+2+2]; cycloaddition; heterocumulene; isocyanate; carbodiimide; carbon dioxide; carbon disulfide; ketene; nitrile; alkyne; diyne; pyridone; pyridine; transition‐metal catalysis

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