Stable Triazenes Derived from 2‐Alkylaminonaphthalenes and 5‐Nitrobenzo[<i>c</i>]‐1,2‐thiazole‐3‐diazonium Hydrogensulfate

Přikryl, Josef; Macháček, Vladimı́r; Jansa, Petr; Svobodová, Markéta; Růžička, Aleš; Nachtigall, Petr; Černý, Michal

doi:10.1002/ejoc.200800180

Cited by 8 publications

(1 citation statement)

References 23 publications

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“…73 Obtained from 1a and 3m using procedure A, followed by E: Yellow oil (142 mg, 95% yield): 1 N-(2′-Naphthylmethyl)-1-butylamine (6i). 74 Obtained from 1b and 3i using procedure A followed by E: White solid (192 mg, 86% yield); mp 225−226 °C (AcOEt−hexane); 1 N-(Cyclohexylmethyl)-2-propen-1-ylamine (6j). 75 Obtained from 1c and 3l using procedure A, followed by E: Yellow oil (139 mg, 88% yield): 1 N-Benzyl-N,N-diethylamine (7a).…”

Section: ■ Conclusionmentioning

confidence: 99%

Reductive Amination Revisited: Reduction of Aldimines with Trichlorosilane Catalyzed by Dimethylformamide─Functional Group Tolerance, Scope, and Limitations

Popov

Campbell

Kysilka³

et al. 2021

J. Org. Chem.

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Aldimines, generated in situ from aliphatic, aromatic, and heteroaromatic aldehydes and aliphatic, aromatic, and heteroaromatic primary or secondary amines, can be reduced with trichlorosilane in the presence of dimethylformamide (DMF) as an organocatalyst (≤10 mol %) in toluene or CH2Cl2 at room temperature. The reduction tolerates ketone carbonyls, esters, amides, nitriles, sulfones, sulfonamides, NO2, SF5, and CF3 groups, boronic esters, azides, phosphine oxides, CC and CC bonds, and ferrocenyl nucleus, but sulfoxides and N-oxides are reduced. α,β-Unsaturated aldimines undergo 1,2-reduction only, leaving the CC bond intact. N-Monoalkylation of primary amines is attained with a 1:1 aldehyde to amine ratio, whereas excess of the aldehyde (≥2:1) allows second alkylation, giving rise to tertiary amines. Reductive N-alkylation of α-amino acids proceeds without racemization; the resulting products, containing a CC bond or N3 group, are suitable for click chemistry. This reaction thus offers advantages over the traditional methods (borohydride reduction or catalytic hydrogenation) in terms of efficiency and chemoselectivity. Solubility of some of the reacting partners appears to be the only limitation. The byproducts generated by the workup with aqueous NaHCO3 (i.e., NaCl and silica) are environmentally benign. As a greener alternative, DMA can be employed as a catalyst instead of DMF.

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Section: ■ Conclusionmentioning

confidence: 99%

Reductive Amination Revisited: Reduction of Aldimines with Trichlorosilane Catalyzed by Dimethylformamide─Functional Group Tolerance, Scope, and Limitations

Popov

Campbell

Kysilka³

et al. 2021

J. Org. Chem.

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Highly Efficient Brønsted Acidic Ionic Liquid Promoted Direct Diazenylation of Pyrazolones with Aryltriazenes under Mild Conditions

Zhang

Liu

et al. 2016

Asian J Org Chem

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We report the first Brønsted acidic ionic liquid (IL) promoted reactiono f5 -pyrazolones with aryltriazenes to prepare arylazopyrazolones. The reaction was carried out with the aryltriazenes as diazotizing agents, water as the solvent, and the ionic liquid as the promoter at room tempera-ture under air and metal-free conditions. The desired products were obtainedi ng ood to excellent yields. Notably, ag ram-scale experiment and al ate-stage diazenylationr eaction of ap harmaceutical derivative alsof urnished the desired products under mild conditions.

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Synthesis of Optically Pure Arylamine Derivatives by Using the Bucherer Reaction

2017

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The Bucherer reaction is a common pathway for the conversion of 1‐ and 2‐naphthols into the corresponding 1‐ or 2‐naphthylamines, respectively. Mostly, only singular examples for its preparative use are reported since this particular transformation seems to be very sensitive to the reaction conditions. By choosing different phenolic substrates and chiral amines, we were able to prepare a broad scope of optically pure arylamines using this type of reaction. In contrast to alternative methods forming C−N aryl bonds such as Buchwald‐Hartwig or Chan‐Lam cross‐coupling reactions, no palladium or copper catalysts are required. The use of water as solvent and the easily available starting materials make this method to an attractive approach.

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Stable Triazenes Derived from 2‐Alkylaminonaphthalenes and 5‐Nitrobenzo[c]‐1,2‐thiazole‐3‐diazonium Hydrogensulfate

Cited by 8 publications

References 23 publications

Reductive Amination Revisited: Reduction of Aldimines with Trichlorosilane Catalyzed by Dimethylformamide─Functional Group Tolerance, Scope, and Limitations

Reductive Amination Revisited: Reduction of Aldimines with Trichlorosilane Catalyzed by Dimethylformamide─Functional Group Tolerance, Scope, and Limitations

Highly Efficient Brønsted Acidic Ionic Liquid Promoted Direct Diazenylation of Pyrazolones with Aryltriazenes under Mild Conditions

Synthesis of Optically Pure Arylamine Derivatives by Using the Bucherer Reaction

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