An Efficient Synthesis of the Anti-asthmatic Agent T-440: A Selective N-Alkylation of 2-Pyridone.

Sugahara, Masakatsu; Moritani, Yasunori; Kuroda, Tooru; Kondo, Kazuyoshi; Shimadzu, Hideshi; Ukita, Tyunosin

doi:10.1248/cpb.48.589

Cited by 23 publications

(4 citation statements)

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“…Treatment of 33 with 36 in the presence of cesium carbonate as a base in DMF was converted to 34 contaminated with ca. 10% of the O -alkylated compound 37 as a major byproduct . Then, 34 was extracted with CHCl 3 and reacted with 5 equivalents of methanesulfonic acid to prompt deprotection of the Boc group.…”

Section: Resultsmentioning

confidence: 99%

Process Development of an Efficient and Cost-Effective Telescoping Route to a Key Synthetic Precursor for the Preparation of a Renin Inhibitor

Nonoyama

Nakai

Lee

et al. 2019

Org. Process Res. Dev.

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Section: Resultsmentioning

confidence: 99%

Process Development of an Efficient and Cost-Effective Telescoping Route to a Key Synthetic Precursor for the Preparation of a Renin Inhibitor

Nonoyama

Nakai

Lee

et al. 2019

Org. Process Res. Dev.

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“…Formation of direct C−N bond can be effected through traditional Cu catalyzed Ullmann type C−N bond formation [132] which requires employment of high temperature and stoichiometric amount of copper reagent. However, there is much progress now in the field of transition metal catalyzed N ‐arylation of pyridones, most significant is the copper catalyzed reactions.The history of C−N bond formation in presence of catalytic transition metals is as recent as 1997 when Ukita reported copper catalyzed N ‐arylation of 2‐hydroxy pyridines using copper halides, oxides and copper powder [133] . Reaction was sensitive to steric hindrance.…”

Section: C−h Bond Activationmentioning

confidence: 99%

Comprehensive Overview of Progress in Functionalization of 2‐Pyridone and 2, 4 ‐Dihydroxy Pyridine: Key Constituents of Vital Natural Products

et al. 2021

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Nitrogen heterocycles have found a key role in biologically active natural products. Pyridones, specifically 2‐pyridone and 2,4‐dihydoxypyridine are an extensive class of compounds with reported occurrence in many natural products. Therefore, the methods for generation of functionalized pyridones are of great interest since their discovery. From traditional coupling to transition metal catalyzed C−H functionalization and transition metal free C−H functionalization, this field has witnessed enormous growth. In the present review, we aim to present a comprehensive overview of pyridone functionalization for young researchers and invite the scientific community to come up with more environment friendly, economic and transition metal free methodologies for corresponding functionalizations.

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“…Selective N-alkylation of 2-pyridone is an interesting area, because N-substitution introduces an element of diversity or, alternatively, a site for further modification via library synthesis [38][39][40]. See, for example, the indolizine formation shown in scheme (1), as an intermediate key in the synthesis of tetracyclic 9H,10H-indolizine [1,2-b]indole-1ones [41].…”

Section: -Pyridones As Building Blocks In Synthesismentioning

confidence: 99%

New Synthetic Methods to 2-Pyridone Rings

Torres¹,

Gil²,

Parra

2005

COC

200

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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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An Efficient Synthesis of the Anti-asthmatic Agent T-440: A Selective N-Alkylation of 2-Pyridone.

Cited by 23 publications

References 0 publications

Process Development of an Efficient and Cost-Effective Telescoping Route to a Key Synthetic Precursor for the Preparation of a Renin Inhibitor

Process Development of an Efficient and Cost-Effective Telescoping Route to a Key Synthetic Precursor for the Preparation of a Renin Inhibitor

Comprehensive Overview of Progress in Functionalization of 2‐Pyridone and 2, 4 ‐Dihydroxy Pyridine: Key Constituents of Vital Natural Products

New Synthetic Methods to 2-Pyridone Rings

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