Organocatalyzed Thia‐Michael Addition and Sequential Inverse Electron Demanding Diels‐Alder Reaction to 3‐Vinyl‐1,2,4‐ triazine Platforms

Berthonneau, Clément; Buttard, Floris; Hiebel, Marie‐Aude; Suzenet, Franck; Brière, Jean‐François

doi:10.1002/adsc.201700831

Cited by 12 publications

(3 citation statements)

References 36 publications

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“…By employing propargylamine derivatives as the starting nucleophiles, the same group also established a sequential aza-Michael addition/IEDDA/retro-Diels–Alder procedure with 3-vinyl-1,2,4-triazines, thus allowing one-pot access to diversely substituted tetrahydro-1,6-naphthyridines 99 (Scheme b) . This strategy could also be extended for the synthesis of 7,8-dihydro-5 H -thiopyrano[4,3- b ]pyridines 100 from 3-vinyl-1,2,4-triazines and propargylthiol derivatives (Scheme b) …”

Section: 24-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: 24-triazinesmentioning

confidence: 99%

“…130 This strategy could also be extended for the synthesis of 7,8-dihydro-5H-thiopyrano[4,3-b]pyridines 100 from 3vinyl-1,2,4-triazines and propargylthiol derivatives (Scheme 29b). 131 2.2.2. Application of 1,2,4-Triazines in the Total Synthesis of Natural Products.…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2021

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“…Moreover, to implement thiol nucleophile (instead of amine) and to access the path for 7,8‐dihydro‐5 H ‐thiopyrano[4,3‐ b ]pyridines ( 61 ) an organo‐catalytic base (DBU) was required to in situ generate the required nucleophile from acetylated thiols (Scheme 24). [32c] …”

Section: Microwave‐assisted Chemistry Of Poly‐aza‐heterocyclesmentioning

confidence: 99%

The Riveting Chemistry of Poly‐aza‐heterocycles Employing Microwave Technique: A Decade Review

et al. 2021

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The application of microwave technique in chemical laboratory rooted back in 1986 and found advantageous over conventional approaches. On the other side, poly‐aza‐heterocycles are influencing organic frameworks with a fascinating chemistry and well explored by employing microwave‐assisted organic reactions. In the present review, we have thoroughly updated rousing literatures of microwave‐assisted synthesis and reactions of various poly‐aza‐heterocycles viz., triazole, tetrazole, triazine, and tetrazine from the past decade (2010–2020). The expedient chemistry and enabling role of microwave heating for adequate chemical transformations of such heterocycles, which were more challenging using classical approaches, are appropriately elucidated. This review also highlights the potential applications of these heterocyclic scaffolds and their derivatives in different scientific domains. Remarkably, such chemical architects possess wide applications as crucial building blocks in synthesis of biologically relevant compounds, agrochemicals, and compounds of interest in material science.

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Copper‐Catalyzed Photoinduced [3+3] Cycloaddition Reactions of α‐Acidic Isocyanides with Tetrazoles

Liu,

Hao,

Cai

et al. 2023

Adv Synth Catal

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Herein, a copper‐catalyzed photoinduced [3+3] cycloaddition reaction of α‐acidic isocyanides with 2,5‐diaryltetrazoles is described. The reaction proceeded smoothly with high regioselectivity, affording a range of important 1,2,4‐triazines under mild conditions. The obtained 1,2,4‐triazines were converted into triazine alcohol, Weinreb amide and triazinone easily, which further illustrate the utility of this [3+3] cycloaddition process.

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Organocatalyzed Thia‐Michael Addition and Sequential Inverse Electron Demanding Diels‐Alder Reaction to 3‐Vinyl‐1,2,4‐ triazine Platforms

Cited by 12 publications

References 36 publications

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

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

The Riveting Chemistry of Poly‐aza‐heterocycles Employing Microwave Technique: A Decade Review

Copper‐Catalyzed Photoinduced [3+3] Cycloaddition Reactions of α‐Acidic Isocyanides with Tetrazoles

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