Intramolecular Huisgen [3+2] cycloaddition in water: synthesis of fused pyrrolidine–triazoles

Kumar, Indresh; Mir, Nisar A.; Rode, C.V.; Wakhloo, Basant P.

doi:10.1016/j.tetasy.2012.02.011

Cited by 16 publications

(7 citation statements)

References 56 publications

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“…Kumar et al reported the synthesis of various pyrrolidine-triazoles, these compounds are achieved by using this intramolecular cycloaddition reaction in water with complete 1,5 regioselectivity [13] (Figure 4).…”

Section: Click Chemistry and Synthesis Of Iminosugars Derivativesmentioning

confidence: 99%

New 1,2,3-Triazole Iminosugars Derivatives Using Click Chemistry

Benhaoua

2012

International Journal of Carbohydrate Chemistry

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Section: Click Chemistry and Synthesis Of Iminosugars Derivativesmentioning

confidence: 99%

New 1,2,3-Triazole Iminosugars Derivatives Using Click Chemistry

Benhaoua

2012

International Journal of Carbohydrate Chemistry

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“…Compounds were prepared with complete 1,5regioselectivity and no metal catalyst. Azido-alkynes derived from amino acid/tartaric acid were used, and an alkyne attached to an electron withdrawing group provided the final product with a better yield and stability (Scheme 58) [100]. Kumar et al, employed an Intramolecular Huisgen [3+2] cycloaddition in water for the preparation of pyrrolidine-triazole derivatives.…”

Section: Reactions In Watermentioning

confidence: 99%

“…better yield and stability (Scheme 58) [100]. Anil et al prepared 1,4-disubstituted 1,2,3-triazoles through magnetically separable and reusable copper ferrite nanoparticles in a one-pot reaction, in tap water.…”

Section: Reactions In Pegmentioning

confidence: 99%

Greener Synthesis of Nitrogen-Containing Heterocycles in Water, PEG, and Bio-Based Solvents

Campos

Berteina‐Raboin

2020

Catalysts

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The solvents used in chemistry are a fundamental element of the environmental performance of processes in corporate and academic laboratories. Their influence on costs, health safety, and nature cannot be neglected. Quantitatively, solvents are the most abundant constituents of chemical transformations; therefore, acting on solvents and replacing standard solvents with safer products can have a great ecological impact. However, not all green solvents are suitable for the wide scope of organic chemistry reactions. A second point to consider is that 50% of pharmaceutical drugs are nitrogen heterocycles compounds. It therefore appeared important to provide an overview of the more ecological methodologies for synthesizing this class of compounds. In this review, all publications since 2000 that describe green reactions leading to the formation of nitrogen heterocycles using safe solvents were considered. We chose water, PEG, and bio-based solvents for their negligible toxicity. The synthesis of five-, six-, and seven-membered aromatic nitrogen heterocycles using green reactions reported in the literature to date is described.

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“…The synthesis of various chiral fused pyrrolidine‐triazoles from azido‐alkyne derived from tartaric acid 125 was reported by Kumar et al . Herein, ʟ‐(+)‐tartaric acid was firstly transformed into azido‐alcohol 126 , which was then subjected to IBX oxidation followed by ohira's conditions to furnish azido‐alkyne 127 , later one was then underwent intramolecular Huisgen cycloaddition in water under thermal conditions to afford chiral fused pyrrolidine‐triazole 128 (Scheme ).…”

Section: Synthesis Of Chiral Fused 123‐triazolesmentioning

confidence: 99%

Chiral Fused 1,2,3‐Triazoles: A Synthetic Overview

2020

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Triazoles have always occupied a pivotal position in the field of medicinal and pharmaceutical chemistry. Recently, the area of chiral fused triazoles has gained attention. The synthetic routes to access chiral fused triazole may involve either a natural or synthetic chiral starting material with a suitably functionalized azide and alkyne component or isomer resolution to achieve chirality. Asymmetric synthesis methods using chiral complexes and organocatalysis have also emerged for obtaining chiral fused triazoles. Herein, we have described an up-to-date overview of different synthetic protocols applied to construct chiral fused 1,2,3-triazoles. Scheme 1. Basic methodologies for triazole construction. 2 3 4 5 6 7 8 . Yanai's stereo-divergent synthesis of ido-triazole ent-6 a and gluco-triazoles 7 a. Scheme 3. Yanai's diastereo-divergent synthesis of manno-, gulo-, galacto-and altro-triazoles. . Konda's synthesis of tricyclic triazolo-oxazepines 62. Scheme 15. Cobb's synthesis of spirocyclic triazolooxazine nucleosides 67. Scheme 16. Sen's synthesis of tetracyclic triazolo-oxazepines 69. to azide group and protected amine was propargylated to access azido-alkynes 122 c-h for triazole formation 124 (Scheme 29). The copper catalyzed version of this step was also carried out that gave almost approximately same yields in lesser Scheme 25. Chrandrasekaran's synthesis of triazolo-pyrazines and pyrazinones from amino acid derived sulfamidates. Scheme 26. Chrandrasekaran's synthesis of triazolo-pyrazinone 110 having pendant amino acid.structural features of triazoles, the authors carried out one pot hydrogenation and insitu Boc-protection of 155 a, followed by azidation and propargylation to afford azido-alkyne 160. Subsequently, thermal azide-alkyne cycloaddition furnished the triazole product 161 in good yield (Scheme 34).Allenyl silanes are extensively used in synthetic organic transformations and provide ready access to enantiopure pyrroles, oxiranes, furans and vinyl silanes. In lewis acid assisted reaction, allenyl silanes work as propargyl anion equivalents. Allenyl silane forms regioselective homopropargylic alcohol when treated with aldehyde and ketone. The stabilization is Scheme 31. Thomas's synthesis of steroidal fused 1,2,3-triazoles.Scheme 32. Thomas's synthesis of steroidal fused NH-1,2,3-triazoles and steroidal 4,5-fused triazolo-alkynes.

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Intramolecular Huisgen [3+2] cycloaddition in water: synthesis of fused pyrrolidine–triazoles

Cited by 16 publications

References 56 publications

New 1,2,3-Triazole Iminosugars Derivatives Using Click Chemistry

New 1,2,3-Triazole Iminosugars Derivatives Using Click Chemistry

Greener Synthesis of Nitrogen-Containing Heterocycles in Water, PEG, and Bio-Based Solvents

Chiral Fused 1,2,3‐Triazoles: A Synthetic Overview

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