Access to pyridines via cascade nucleophilic addition reaction of 1,2,3-triazines with activated ketones or acetonitriles

Zhang, Yuan; Luo, Han; Lu, Qixing; An, Qiaoyu; Li, You; S, Li; Tang, Zongyuan; Li, Baosheng

doi:10.1016/j.cclet.2020.03.075

Cited by 17 publications

(20 citation statements)

References 49 publications

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“…Most recently, Li and co-workers disclosed a facile basepromoted IEDDA reaction of 1,2,3-triazines 147 with activated acetonitriles 148 or ketones 150 (Scheme 47a,b). 174 In contrast to the concerted mechanism for the conventional IEDDA reactions, this reaction was postulated to proceed via a stepwise pathway. In the presence of base, the nucleophilic addition of activated acetonitriles 148 or ketones 150 Although the normal IEDDA reactions of 1,2,3-triazines prefer to proceed via the C4/N1 (C6/N3) mode, the cycloaddition pattern could be tuned to C5/N2 mode in some cases.…”

Section: Ring-expansionmentioning

confidence: 99%

“…As a result, pyridine 167 were generated with relatively high efficiency (75% yield) as a single regioisomer via exclusive C4/N1 cycloaddition selectivity, which is in line with the general cycloaddition mode for C5substituted 1,2,3-triazines. Methoxatin (174), also known as pyrroloquinoline quinone (PQQ), is redox active compound existing in a range of methylotrophic bacteria. 186 It was demonstrated to play an important role in various biological processes in mammalians, such as dietary supplement and reducing the injury risk in stroke and heart attack.…”

Section: Ring-expansionmentioning

confidence: 99%

“…Most recently, Li and co-workers disclosed a facile base-promoted IEDDA reaction of 1,2,3-triazines 147 with activated acetonitriles 148 or ketones 150 (Scheme a,b) . In contrast to the concerted mechanism for the conventional IEDDA reactions, this reaction was postulated to proceed via a stepwise pathway.…”

Section: 23-triazinesmentioning

confidence: 99%

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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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Section: Ring-expansionmentioning

confidence: 99%

Section: Ring-expansionmentioning

confidence: 99%

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

et al. 2021

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“…[2][3][4][5][6][7][8] Furthermore, triazines are known to undergo various transformations with suitable substrates (inverse-electron demand Diels-Alder reactions, 9 addition/elimination/cyclization reactions 10,11 ), which allows their conversion into other N-heterocycles of interest, e.g. pyridines, 12,13 pyrimidines, 10 and pyridazines. 14 Taken together, methods for the preparation of triazines do not only allow for direct access to molecules of potential pharmaceutical interest, but also provide a platform for the synthesis of additional N containing heterocycles.…”

mentioning

confidence: 99%

Cross-Coupling Reactions of 5-Bromo-1,2,3-triazines

Hoff

Hauser

Gademann

2022

Preprint

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An efficient Pd catalyzed cross-coupling method for 5-bromo-1,2,3-triazine is described. Optimization of the reaction conditions al-lowed for the preparation of a representative scope of (hetero)aryl-1,2,3-triazines (14 examples, up to 97% yield). Additionally, diversifi-cation of the resulting products enabled the preparation of pyrimidines and pyridines in yields of up to 80% and in only two steps.

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“…Divergent synthesis provides quick access to structurally diversified chemical scaffolds that are crucial to building a molecule library for drug screening and discovery . Moreover, multicomponent cascade reactions, which consist of merging compatible single-bond-forming processes, allow multiple chemical events between several substrates .…”

mentioning

confidence: 99%

Divergent Synthesis of Highly Substituted Pyridines and Benzenes from Dienals, Alkynes, and Sulfonyl Azides

Luo

et al. 2021

Org. Lett.

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Divergent synthesis is extremely important for the highly efficient preparation of structurally diverse target molecules. Herein, we describe a multicomponent cascade reaction, which allows access to highly substituted pyridines and benzenes by combining four individual steps in a one-pot manner from the same set of readily available starting materials. The azepine intermediates were first used as the precursors for 6π-electrocyclization to construct highly substituted pyridines and benzenes in a tunable manner.

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Access to pyridines via cascade nucleophilic addition reaction of 1,2,3-triazines with activated ketones or acetonitriles

Cited by 17 publications

References 49 publications

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

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

Cross-Coupling Reactions of 5-Bromo-1,2,3-triazines

Divergent Synthesis of Highly Substituted Pyridines and Benzenes from Dienals, Alkynes, and Sulfonyl Azides

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