A highly efficient multicomponent synthesis of pyridones and pyrimidones by a [2+2+2] strategy

Ghosez, Léon; Jnoff, Eric; Bayard, Philippe; Sainte, Francy; Beaudegnies, Renaud

doi:10.1016/s0040-4020(98)01149-1

Cited by 51 publications

(20 citation statements)

References 18 publications

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“…Hydrolysis or methanolysis gave good yields of substituted pyridones [191]. The primary adduct spontaneously losses an alcohol or silanol molecule.…”

Section: Miscelanous Cyclizationsmentioning

confidence: 99%

New Synthetic Methods to 2-Pyridone Rings

Torres¹,

Gil²,

Parra

2005

COC

203

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The synthesis of a substituted 2-pyridone ring is a topical area of continuing interest due to the number of biologically active molecules containing this moiety. Over the last decade, natural compounds with this structure have emerged as potent antitumor antiviral and attention, because those compounds may be studied as a simple model for investigating mechanisms of some enzymatic reactions or for discerning the behavior of nucleic acids bases in connection with mutation due to base mispairing or other mistaken helices. Recent studies have shown the usefulness of 2-pyridones as intermolecular connectors between building blocks in material science. Thus, despite the large number of methods known for their synthesis, new procedures are continuously being developed. Two main synthetic approaches can be found in the literature: from other heterocycles systems or condensation of acyclic systems. The latter can be further classified depending on the bond formed in the cyclization step: by C-C or C-N bond generation. The latter can be subclassified depending on the first condensation step. This is a review of new or improved methods for constructing 2-pyridone rings. This article will be restricted to ring formation, which can be included in the total synthesis of several compounds with specific biological or material properties.The pursuit of these properties requires efficient synthetic routes that allow rapid assembly and variation of multiple pendant substituents on the heteroaromatic case, which permits rapid analogsynthesis (RAS) [1].

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“…Hydrolysis or methanolysis gave good yields of substituted pyridones [191]. The primary adduct spontaneously losses an alcohol or silanol molecule.…”

Section: Miscelanous Cyclizationsmentioning

confidence: 99%

New Synthetic Methods to 2-Pyridone Rings

Torres¹,

Gil²,

Parra

2005

COC

203

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“…[1][2][3][4] In this area, we and other research group [5][6][7][8][9] have been interested in the use of functionalized azadiene system 1 (Scheme 1) for the preparation of heterocyclic compounds, such as β-lactam rings, by a two-step Staudinger reaction, [10][11][12] as well as tetramic acid scaffolds, [13] perhydrooxazin-2-ones, cyclic intermediates in the synthesis of α-amino β-hydroxy acids, [14,15] β-hydroxycarboxylic acids, [16] and 1,3-aminols, through a hetero-Diels-Alder (HDA) approach. [17][18][19][20] Some processes have been performed by taking advantage of microwave-assisted organic synthesis (MAOS) technology.…”

Section: Introductionmentioning

confidence: 99%

Hetero‐Diels–Alder (HDA) Strategy for the Preparation of 6‐Aryl‐ and Heteroaryl‐Substituted Piperidin‐2‐one Scaffolds: Experimental and Theoretical Studies

et al. 2011

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“…For more than a century, many diverse methods have been developed to prepare pyridines with various ring substitution patterns [5][6][7][8][9]. The majority of synthesis routes to pyridine and quinoline derivatives rely on condensation reactions of amines and carbonyl compounds [10][11][12].…”

Section: Introductionmentioning

confidence: 99%