Synthesis of Pyridazine Derivatives via Aza-Diels–Alder Reactions of 1,2,3-Triazine Derivatives and 1-Propynylamines

Kodama, Takayuki; Sasaki, Ikuo; Sugimura, Hideyuki

doi:10.1021/acs.joc.1c00851

Cited by 12 publications

(9 citation statements)

References 31 publications

(28 reference statements)

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“…A year later, Kodama and co-workers synthesized pyridazine derivative 28 through the reaction of 1,2,3-triazine derivative 26 with N,N-di-p-methoxybenzyl-1-propyn-1-amine (27) via aza-Diels-Alder reaction in dry 1,4-dioxane (Scheme 13) (Kodama et al, 2021). S C H E M E Synthesis of pyridazine derivative 28.…”

Section: Conventional Methods Of Pyridazine Pyridazinone and Fused Py...mentioning

confidence: 99%

Pyridazine derivatives as selective COX‐2 inhibitors: A review on recent updates

Ewieda,

Ahmed,

Hassan

et al. 2023

Drug Development Research

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Selective cyclooxygenase (COX)‐2 inhibitors have several advantages over nonselective COX inhibitors (nonsteroidal anti‐inflammatory drugs [NSAIDs]), including the absence of adverse effects (renal and hepatic disorders) associated with the long‐term use of standard NSAIDs, as well as an improved gastrointestinal profile. The pyridazine nucleus is regarded as a promising scaffold for the development of powerful COX‐2 inhibitors, particularly when selectively functionalized. This article summarizes some methods for the synthesis of pyridazine derivatives. Furthermore, it covers all of the pyridazine derivatives that have appeared as selective COX‐2 inhibitors, making it useful as a reference for the rational design of novel selective COX‐2 inhibitors.

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Section: Conventional Methods Of Pyridazine Pyridazinone and Fused Py...mentioning

confidence: 99%

Pyridazine derivatives as selective COX‐2 inhibitors: A review on recent updates

Ewieda,

Ahmed,

Hassan

et al. 2023

Drug Development Research

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“…In our laboratory, we have developed several novel reactions that provide easy access to useful functionalized N-containing heterocycles of chemical and biological interest. [7][8][9] As a continuation of our research investigating multicomponent reaction using α,γ-diazido-α,β-unsaturated esters, we herein report a novel for the construction of 5,6-dihydropyrrolo [3,4-b]pyrrol-4(1H)-ones.…”

Section: Scopementioning

confidence: 99%

Synthesis of Polysubstituted 5,6-Dihydropyrrolo[3,4-b]pyrrol-4(1H)-ones from 2-[Aryl(azido)methyl]-1H-pyrrole-3-carboxylates via a Concise Three-Step Sequence

Sugimura¹,

Nomura²,

Ohta³

et al. 2022

HETEROCYCLES

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“…Very recently, Sugimura and co-workers also took advantage of the IEDDA reaction of disubstituted 1,2,3triazines with 1-propynylamines to make a series of 6-arylpyridazin-3-amines in good yields with excellent C5/N2 selectivity. 175 3.2.2. Application of 1,2,3-Triazines in the Total Synthesis of Natural Products.…”

Section: Ring-expansionmentioning

confidence: 99%

“…By contrast, in the cases of 152a and 152b , where C6 is unsubstituted and sterically accessible or C5 is substituted and sterically less accessible, a small amount of C4/N1 cycloaddition was accompanied to deliver the pyridine side products 154 and 156 in 3–12% yields (Scheme a,b). Very recently, Sugimura and co-workers also took advantage of the IEDDA reaction of disubstituted 1,2,3-triazines with 1-propynylamines to make a series of 6-aryl-pyridazin-3-amines in good yields with excellent C5/N2 selectivity …”

Section: 23-triazinesmentioning

confidence: 99%

Triazines: Syntheses and Inverse Electron-demand Diels–Alder Reactions

et al. 2021

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Triazines are an important class of six-membered aromatic heterocycles possessing three nitrogen atoms, resulting in three types of regio-isomers: 1,2,4-triazines (a-triazines), 1,2,3-triazines (v-triazines), and 1,3,5-triazines (s-triazines). Notably, the application of triazines as cyclic aza-dienes in inverse electron-demand Diels–Alder (IEDDA) cycloaddition reactions has been established as a unique and powerful method in N-heterocycle synthesis, natural product preparation, and bioorthogonal chemistry. In this review, we comprehensively summarize the advances in the construction of these triazines via annulation and ring-expansion reactions, especially emphasizing recent developments and challenges. The synthetic transformations of triazines are focused on IEDDA cycloaddition reactions, which have allowed access to a wide scope of heterocycles, including pyridines, carbolines, azepines, pyridazines, pyrazines, and pyrimidines. The utilization of triazine IEDDA reactions as key steps in natural product synthesis is also discussed. More importantly, a particular attention is paid on the bioorthogonal application of triazines in fast click ligation with various strained alkenes and alkynes, which opens a new opportunity for studying biomolecules in chemical biology.

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Synthesis of Pyridazine Derivatives via Aza-Diels–Alder Reactions of 1,2,3-Triazine Derivatives and 1-Propynylamines

Cited by 12 publications

References 31 publications

Pyridazine derivatives as selective COX‐2 inhibitors: A review on recent updates

Pyridazine derivatives as selective COX‐2 inhibitors: A review on recent updates

Synthesis of Polysubstituted 5,6-Dihydropyrrolo[3,4-b]pyrrol-4(1H)-ones from 2-[Aryl(azido)methyl]-1H-pyrrole-3-carboxylates via a Concise Three-Step Sequence

Triazines: Syntheses and Inverse Electron-demand Diels–Alder Reactions

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