Efficient synthesis of conformationally constrained, amino-triazoloazepinone-containing di- and tripeptides via a one-pot Ugi–Huisgen tandem reaction

Barlow, Thomas; Jida, Mouhamad; Tourwé, Dirk; Ballet, Steven

doi:10.1039/c4ob01381f

Cited by 32 publications

(33 citation statements)

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“…The authors also developed a catalyst free, one pot synthesis of conformationally constrained amino‐triazolodiazepines having di and tripeptides . Their methodology applies Ugi‐4CR between propargylamine, β ‐azido‐ α ‐amino acids 117 , different aldehydes 118 and isocyanides 119 at room temperature to afford alkyne‐azide intermediate, which on heating underwent Huisgen cycloaddition to finally furnish triazoles 120 in good to excellent yields (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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Section: Synthesis Of Chiral Fused 123‐triazolesmentioning

confidence: 99%

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

2020

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“…Related structures featuring seven‐membered rings were accessed by Barlow and co‐workers. A tandem Ugi‐4CR followed by thermal Huisgen cyclisation was applied to design a library of aminotriazolodiazepine di‐ and tripeptides of type 55 by starting from Boc‐β‐azidoalanine ( 54 ; Scheme ). These reactions were typically high‐yielding (up to 94 %) and operationally simple (one‐pot, two‐step) and offered considerable improvements in terms of yield and efficiency over previous routes to these molecules, which employed RuAAC in combination with lactamisation .…”

Section: Application Of Aac Reactions For the Synthesis Of Small (mentioning

confidence: 99%

Cyclisation To Form Small, Medium and Large Rings by Use of Catalysed and Uncatalysed Azide–Alkyne Cycloadditions (AACs)

2017

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This microreview briefly summarises recent developments in cyclisation to afford small, medium and large rings (five to 30 members) by way of both catalysed and uncatalysed azide–alkyne cycloaddition (AAC). The standard AAC reactions – intramolecular Huisgen, CuAAC and RuAAC – are presented, as well as some of their contemporary variations. In addition, we present useful strategies for overcoming common problems encountered in these reactions.

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“…[12,13] In recent years the copper(I)-catalyzed azide alkyne cycloaddition (CuAAC), the most frequently used "click" reaction, have emerged as efficient methodologies for the construction of a range of different macrocyclic structures for different purposes. [14][15][16] CuAAC has been utilized as an efficient protocol to close macrocycles of different sizes by the formation of 1,4-triazoles. [14][15][16][17] During our previous investigation we demonstrated the possibility for construction of macrocyclic compounds on the furan ring of lambertianic acid derivatives.…”

Section: Synthesis Of Novel Labdanoid-based Macroheterocyclesmentioning

confidence: 99%

“…[14][15][16] CuAAC has been utilized as an efficient protocol to close macrocycles of different sizes by the formation of 1,4-triazoles. [14][15][16][17] During our previous investigation we demonstrated the possibility for construction of macrocyclic compounds on the furan ring of lambertianic acid derivatives. Furanolabdanoid with 1,2,3-triazole-incorporated macrocycles at C-16 position [18] and furan bridged macrocyclic compounds [19] were obtained and characterized.…”

Section: Synthesis Of Novel Labdanoid-based Macroheterocyclesmentioning

confidence: 99%