New insight on the cycloaddition of aryl and heteroaryl azides with (trimethylsilyl)acetylene. Spectroscopic and x-ray crystallographic data of silylated 1,2,3-triazoles

Businelli, Silvia; Martino, Emanuela Di; Zanirato, Paolo

doi:10.3998/ark.5550190.0002.108

Cited by 5 publications

(1 citation statement)

References 11 publications

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“…The successful outcome of the azido transfer reaction in these instances prompted us to study the preparation of two novel simple azidoazoles, 5-azido-1-methyl-1H-imidazole ( 6) and 5azido-1,3-thiazole (7).…”

Section: Resultsmentioning

confidence: 99%

On the utility of the azido transfer protocol: synthesis of 2- and 5-azido N-methylimidazoles, 1,3-thiazoles and N-methylpyrazole and their conversion to triazole–azole bisheteroaryls

Zanirato

Cerini

2005

Org. Biomol. Chem.

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The azido transfer procedure of heteroaryllithium and tosyl azide was used to synthesize selected 2- and 5-azidoazoles. This procedure, which is based on the fragmentation of the appropriate lithium triazene salts 1a-7a, successfully afforded 2-azido-N-methylimidazole 1, 2-azido-1,3-thiazole 2, 2-azidobenzo-1,3-thiazole 3, 5-azido-N-methylpyrazole 4, 5-azido-N-methylimidazole 6[via 2-(trimethylsilyl)-5-azido-N-methylimidazole 5], and 5-azido-1,3-thiazole 7 (via 5-lithio-1,3-thiazole), but attempts to prepare 5-azido-2-(trimethylsilyl)-1,3-thiazole 8 from the corresponding triazene 7a failed, affording only the desilylated azide in poor yield. Azides - underwent 1,3-dipolar cycloaddition when mixed with neat (trimethylsilyl)acetylene, giving 1-heteroaryl-4-trimethylsilyl-1,2,3-triazoles 1b-7b generally in very high yields.

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Section: Resultsmentioning

confidence: 99%

On the utility of the azido transfer protocol: synthesis of 2- and 5-azido N-methylimidazoles, 1,3-thiazoles and N-methylpyrazole and their conversion to triazole–azole bisheteroaryls

Zanirato

Cerini

2005

Org. Biomol. Chem.

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Metal‐Free 1,5‐Regioselective Azide–Alkyne [3+2]‐Cycloaddition

Kloß

Köhn

Jahn

et al. 2011

Chemistry An Asian Journal

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[3+2]‐cycloaddition reactions of aromatic azides and silylated alkynes in aqueous media yield 1,5‐disubstituted‐4‐(trimethyl‐silyl)‐1H‐1,2,3‐triazoles. The formation of the 1,5‐isomer is highly favored in this metal‐free cycloaddition, which could be proven by 1D selective NOESY and X‐ray investigations. Additionally, DFT calculations corroborate the outstanding favoritism regarding the 1,5‐isomer. The described method provides a simple alternative protocol to metal‐catalyzed “click chemistry” procedures, widening the scope for regioselective heavy‐metal‐free synthetic applications.

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Photochemical Reactivity of 2‐Azido‐1,3‐thiazole and 2‐Azido‐1,3‐benzothiazole: A Procedure for the Aziridination of Enol Ethers

et al. 2009

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Direct irradiation of a mixture of the azido–tetrazole tautomers of 2‐azido‐1,3‐thiazole and 2‐azido‐1,3‐benzothiazole in toluene solution gives products arising from the intermediate nitrene, which in turn undergoes ring opening in the case of 2‐azido‐1,3‐thiazole to give a polymer, and dimerization in the case of 2‐azido‐1,3‐benzothiazole to give [1,3]benzothiazolo[2′,3′:3,4][1,2,4,5]tetraazino[6,1b][1,3]benzothiazolein low yields. When irradiation is performed in the presence of methyl acrylate or various enol ethers, aziridination of the double bond is observed, with good yields in the case of enol ethers. Among these, 1‐(6‐methyl‐3,4‐dihydro‐2H‐pyran‐2‐yl)ethanone undergoes aziridination with complete diastereoselectivity to give the (1RS,3RS,6SR) diastereomer.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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New insight on the cycloaddition of aryl and heteroaryl azides with (trimethylsilyl)acetylene. Spectroscopic and x-ray crystallographic data of silylated 1,2,3-triazoles

Cited by 5 publications

References 11 publications

On the utility of the azido transfer protocol: synthesis of 2- and 5-azido N-methylimidazoles, 1,3-thiazoles and N-methylpyrazole and their conversion to triazole–azole bisheteroaryls

On the utility of the azido transfer protocol: synthesis of 2- and 5-azido N-methylimidazoles, 1,3-thiazoles and N-methylpyrazole and their conversion to triazole–azole bisheteroaryls

Metal‐Free 1,5‐Regioselective Azide–Alkyne [3+2]‐Cycloaddition

Photochemical Reactivity of 2‐Azido‐1,3‐thiazole and 2‐Azido‐1,3‐benzothiazole: A Procedure for the Aziridination of Enol Ethers

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