Aminomethylation of lithiated nicotinamide: access to new pyridolactams

Prieur, Emilie; Azzouz, Rabah; Deguest, Geoffrey; Fruit, Corinne; Bischoff, Laurent; Marsais, Francis

doi:10.1016/j.tetlet.2007.11.109

Cited by 5 publications

(1 citation statement)

References 23 publications

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“…Commercially available reagents were used without further purification. T + BF 4 – , and N -alkylanilines 1aa (−CH 2 COPh), 1ba (−CH 2 PO(OEt) 2 ), 1ca (−CH 2 CN), 1da (−CH 2 -oxazolidinone), 1ea , (−CH 2 Ph), and 1fa (−CH 2 Et) were prepared following literature procedures. Except for the reactions carried out under an air or O 2 atmosphere, the catalytic reactions were performed in sealed tubes under an argon atmosphere.…”

Section: Methodsmentioning

confidence: 99%

Iron-Catalyzed Oxidative Tandem Reactions with TEMPO Oxoammonium Salts: Synthesis of Dihydroquinazolines and Quinolines

et al. 2013

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A straightforward iron-catalyzed divergent oxidative tandem synthesis of dihydroquinazolines and quinolines from N-alkylanilines using a TEMPO oxoammonium salt as a mild and nontoxic oxidant has been developed. Fe(OTf)2 was the Lewis acid catalyst of choice for the formation of dihydroquinazolines, whereas FeCl3 led to better results for the synthesis of quinolines. This divergent approach implies that, for both syntheses, direct oxidative functionalization of a α-C(sp(3))-H bond of the N-alkylanilines occurs, leading to C-N bond formation or C-C bond formation upon homocondensation or reaction with simple olefins, respectively. Cyclization followed by a final oxidation generates these classes of interesting bioactive heterocycles in one synthetic transformation. Additionally, the one-pot multicomponent synthesis of quinolines from anilines, aldehydes, and olefins has also been successfully developed under these mild oxidative conditions.

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Section: Methodsmentioning

confidence: 99%

Iron-Catalyzed Oxidative Tandem Reactions with TEMPO Oxoammonium Salts: Synthesis of Dihydroquinazolines and Quinolines

et al. 2013

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Strecker Reactions of Formaldehyde with TMSCN, Catalyzed by TBAF and Formic Acid: N‐Monocyanomethylation of Primary Amines

Liu

Zhang

et al. 2022

Adv Synth Catal

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A set of conditions for the Strecker reaction of formaldehyde, amines, and TMSCN that affords three-component coupling adducts as the major products is reported. HCOOH and TBAF are used as cocatalysts and the TMSCN functions as both cyanide source and protecting reagent for amines. As a result, the side reactions were suppressed efficiently and a broad range of aromatic and aliphatic amines were mono-cyanomethylated in 52-99% yield. Furthermore, this protocol was successfully applied toward the synthesis of metadiamide insecticides.

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ChemInform Abstract: Aminomethylation of Lithiated Nicotinamide: Access to New Pyridolactams.

Prieur¹,

Azzouz²,

Deguest³

et al. 2008

ChemInform

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Fused pyridine derivatives R 0450Aminomethylation of Lithiated Nicotinamide: Access to New Pyridolactams. -Lithiated nicotinamide and cyanomethylamines undergo tandem aminomethylation-cyclization reaction to provide the desired heterocyclic skeleton. Substrates (II) are easily prepared from chloroacetonitrile and the appropriate amines. -(PRIEUR, E.; AZZOUZ, R.; DEGUEST, G.; FRUIT, C.; BISCHOFF*, L.; MARSAIS, F.; Tetrahedron Lett. 49 (2008) 3, 437-440; Lab. Chim. Org. Fine Heterocycl., IRCOF, Inst. Natl. Sci. Appl. Rouen, F-76131 Mont-Saint-Aignan, Fr.; Eng.) -Mais 18-141

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Aminomethylation of lithiated nicotinamide: access to new pyridolactams

Cited by 5 publications

References 23 publications

Iron-Catalyzed Oxidative Tandem Reactions with TEMPO Oxoammonium Salts: Synthesis of Dihydroquinazolines and Quinolines

Iron-Catalyzed Oxidative Tandem Reactions with TEMPO Oxoammonium Salts: Synthesis of Dihydroquinazolines and Quinolines

Strecker Reactions of Formaldehyde with TMSCN, Catalyzed by TBAF and Formic Acid: N‐Monocyanomethylation of Primary Amines

ChemInform Abstract: Aminomethylation of Lithiated Nicotinamide: Access to New Pyridolactams.

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