Aminolysis of allyl esters with bislithium aryl amides

Faler, Catherine A.; Joullié, Madeleine M.

doi:10.1016/j.tetlet.2006.07.136

Cited by 22 publications

(15 citation statements)

References 22 publications

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“…Na 2 SO 4 ), and concentrated. The residue was filtered through a short pad of silica gel (60-120 mesh, Spectrochem, India) using EtOAc-PE (2:3) as an eluent to afford a white crystalline solid; yield: 187 mg (85%); mp 210-212°C (lit 29. 214-216°C).…”

mentioning

confidence: 99%

Efficient Iodine-Mediated Beckmann Rearrangement of Ketoximes to Amides under Mild Neutral Conditions

Ganguly¹,

Mondal²

2010

Synthesis

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Aryl ketoximes readily underwent Beckmann rearrangement to give N-substituted amides in excellent yields on electrophilic activation by elemental iodine in anhydrous acetonitrile under reflux. The main advantages of this environmentally friendly protocol include a high selectivity as a result of the absence of any accompanying deprotection to form the parent ketones as byproducts, mild neutral conditions, procedural simplicity, and particularly ease of isolation of the products.

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confidence: 99%

Efficient Iodine-Mediated Beckmann Rearrangement of Ketoximes to Amides under Mild Neutral Conditions

Ganguly¹,

Mondal²

2010

Synthesis

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“…Solvent system for flash chromatography: Petroleum ether/Ethyl acetate: 3/1, R f = 0.5; mp: 77–78 °C ([lit. ]: 81–83 °C); 1 H NMR (500 MHz, CDCl 3 ): δ 9.03 (s, 1H), 8.43–8.41 (m, 1H), 8.22–8.20 (m, 1H), 7.95–7.94 (m, 2H), 7.78–7.75 (m, 1H), 7.59–7.55 (m, 1H), 7.51–7.48 (m, 2H), 7.07–7.04 (m, 1H).…”

Section: Experimental Sectionmentioning

confidence: 99%

Copper-Catalyzed Tandem Reactions of 2-Amine-[1,3,5]triazines with Nitriles

Zhang

Wang

et al. 2018

J. Org. Chem.

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Copper-catalyzed intermolecular annulation of 2-amine-[1,3,5]triazines and aryl nitriles for the synthesis of [1,2,4]triazolo[1,5-a][1,3,5]triazines via N–C bond formation and oxidative N–N coupling [oxidative 3 + 2 cyclization] is presented. A wide range of aryl nitriles, including electron-rich benzonitriles, electron-poor benzonitriles, 2-cyanothiophene, and 4-cyanopyridine, were all functionalized with 2-amine-[1,3,5]triazines. Furthermore, amidation of 2-amine-[1,3,5]triazines via Cu-catalyzed C–CN bond cleavage of phenylacetonitriles is also demonstrated. The reaction occurred in moderate to satisfactory yields and tolerated alkyl- or aryl-substituted 2-amine-[1,3,5]triazines. Aniline, aminopyridine, and aminopyrimidine also afforded the desired products.

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“…Spectral data are consistent with those in the literature. 27 N-(2-Chloro-4-fluorophenyl)benzamide (9h). General procedure A was followed using 2-chloro-4-fluoroaniline (2.0 g, 14.0 mmol) and benzoyl chloride (1.9 mL, 17.0 mmol).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Palladium-Catalyzed Synthesis of Benzimidazoles and Quinazolinones from Common Precursors

et al. 2012

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N-(o-Halophenyl)imidoyl chlorides and the corresponding imidates are easily prepared and can be utilized as complementary precursors for the synthesis of important heterocycles. The synthesis of N-substituted benzimidazoles was possible from the palladium-catalyzed reaction of both classes of substrate with a variety of N-nucleophiles. The use of the imidate precursor for the synthesis of N-substituted quinazolinones by incorporation of a palladium-catalyzed aminocarbonylation reaction has also been demonstrated. Both processes tolerate a wide range of functional groups.

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Aminolysis of allyl esters with bislithium aryl amides

Cited by 22 publications

References 22 publications

Efficient Iodine-Mediated Beckmann Rearrangement of Ketoximes to Amides under Mild Neutral Conditions

Efficient Iodine-Mediated Beckmann Rearrangement of Ketoximes to Amides under Mild Neutral Conditions

Copper-Catalyzed Tandem Reactions of 2-Amine-[1,3,5]triazines with Nitriles

Palladium-Catalyzed Synthesis of Benzimidazoles and Quinazolinones from Common Precursors

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