Selective N-acetylation of aromatic amines using acetonitrile as acylating agent

Saikia, Ujwal Pratim; Hussain, Farhaz Liaquat; Suri, Mrinaly; Pahari, Pallab

doi:10.1016/j.tetlet.2016.01.108

Cited by 33 publications

(20 citation statements)

References 39 publications

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“…However, amine 1s did not afford the corresponding acetanilide, being recovered. This fact is in contrast with the work of Pahari and co-workers, 17 which successfully synthesized the corresponding acetanilide of 3-hydroxy-aniline using acetonitrile as acylating reagent.…”

Section: Resultscontrasting

confidence: 69%

“…To all synthesized acetamides, measured physical data were in agreement to the reported values. [17][18][19]27,31,32 …”

Section: Methodsmentioning

confidence: 99%

“…5,[9][10][11][12][13] Due to the abovementioned applications, new developments in the acetylation procedure are still desirables, and representative contributions are described, Figure 2. [14][15][16][17][18][19][20][21][22][23][24] Furthermore, in undergraduate courses, the parent acetanilide is extensively synthesized as classical preparation of aromatic amide. 25 Therefore, we recently developed a practical solvent-free green synthesis of such compound to experimental courses.…”

Section: Introductionmentioning

confidence: 99%

“…To all synthesized acetamides, measured physical data were in agreement to the reported values. [17][18][19]27,31, 3304, 3261, 3194, 3130, 3095, 1674, 1645, 1598, 1550, 1529, 1477, 1425, 1369, 1350, 1325, 1294, 1261, 1163, 1078, 1016, 983, 887, 823, 808, 742, 711, 603 6, 114.4, 118.9, 125.4, 129.9, 138.9, Yellow solid, 76.5 mg, 86% yield; m.p. 212.9-213.9 °C (Lit.…”

mentioning

confidence: 99%

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Eco-Friendly, Catalyst and Solvent-Free, Synthesis of Acetanilides and N-Benzothiazole-2-yl-acetamides

Cunha¹,

Santana²

2016

J. Braz. Chem. Soc.

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An expeditious and green synthesis of acetamides in a solvent-free simple way is described, without catalyst or additives, and in good yield by an instantaneous reaction of anilines or 2-aminothiazoles and acetic anhydride without external heating, and with simple purification. Sixteen substituted acetanilides and four N-benzothiazole-2-yl-acetamides were formed, but aliphatic amines of low molecular weight were not as effective as aromatic ones, and only cyclohexylamine and the enaminone ethyl 3-amino-2-butenoate afforded the corresponding acetamides in good yield.Keywords: acetylation, acetamides, amides, solvente-free reaction, green chemistry IntroductionIn the modern synthetic chemistry the development of greener approaches to the functional group transformations is of continuous interest. 1 There are several ongoing efforts to develop methods which do not need solvent, additives, and without tedious purification. Even reactions carried out without heating and magnetic stirring are relevant contributions, due to the energy economy aspects. 2 The acetamide/acetanilide are functional groups whose importance is beyond of a simple protecting group. For instance, in medicinal chemistry they play a pivotal role affording chemically stable compounds as prodrugs with improved pharmacological profile, and many N-acylated derivatives are in clinical use. 3 On the other hand, acetanilides have natural aptitude to act as ortho directing group in C−H transformations to C−C bond formation, wherein functionalized benzophenone, 4 quinone, 5 bisphenyl, 6 or styrene 7,8 derivatives can be obtained by Pd or Rh catalysis, Figure 1. Besides, the reactivity of some ortho functional group of acetanilides is modulated by the presence of the N-acetyl moiety, which is thus selectively converted to more complex compound, constituting this kind of acetanilide into important synthetic intermediates. 5,[9][10][11][12][13] Due to the abovementioned applications, new developments in the acetylation procedure are still desirables, and representative contributions are described, Figure 2.14-24 Furthermore, in undergraduate courses, the parent acetanilide is extensively synthesized as classical preparation of aromatic amide.25 Therefore, we recently developed a practical solvent-free green synthesis of such compound to experimental courses. 26 However, a search in the literature revealed that when other substituted acetanilides are needed as starting material in the context of a research project, the preparation used is very similar to that of parent acentanilide, which is almost the same of one century ago, which uses large amounts of solvents and additives such as acetic acid and sodium acetate, for instance. [5][6][7][8][9][10][11][12][13][14][15][19][20][21][22][23][24] It should be pointed out that, although there are a few syntheses of acetanilides in the absence of solvent, it is always necessary the use of grinding or microwave heating in these previously described syntheses or, more recurrent, the use of catalyst such as morpholiniu...

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Section: Resultscontrasting

confidence: 69%

“…To all synthesized acetamides, measured physical data were in agreement to the reported values. [17][18][19]27,31,32 …”

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

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Eco-Friendly, Catalyst and Solvent-Free, Synthesis of Acetanilides and N-Benzothiazole-2-yl-acetamides

Cunha¹,

Santana²

2016

J. Braz. Chem. Soc.

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“…[20a] Thus, it is highly desirable to search for a more convenient and efficient approach to the synthesis of these skeletons. Recent reports from our lab have shown that the treatment of amines with nitriles in the presence of Lewis acids such as trimethylsilyl iodide (TMSI) led to the in‐situ generation of amidines, which, upon hydrolysis, were converted into acetamides …”

Section: Introductionmentioning

confidence: 99%

Lewis‐Acid‐Catalysed Activation of Nitriles: A Microwave‐Assisted Solvent‐Free Synthesis of 2,4‐Disubstituted Quinazolines and 1,3‐Diazaspiro[5.5]undec‐1‐enes

2018

Self Cite

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Two different modes of cyclization take place to synthesize quinazoline, quinazolinone, and 1,3‐diazaspiro[5.5]undec‐1‐ene derivatives through the Lewis‐acid‐catalysed activation of both aliphatic and aromatic nitriles in a single‐step, solvent‐free, and transition‐metal‐free reaction. An amidine is expected to form as an intermediate; this then undergoes intramolecular cyclization in a one‐pot reaction sequence. The reaction is carried out under microwave irradiation using trimethylsilyltrifluoromethane sulfonate (TMSOTf) as a catalyst and nitriles as a nitrogen source with the respective reaction partners.

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Cobalt Single‐Atom Catalyst: Synthesis, Characterization and Catalytic Activity

Syal,

Gupta

2024

Applied Organom Chemis

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One‐pot synthesis of acetamides, benzimidazoles, and benzothiazoles are central reactions for synthesizing pharmaceuticals and fine chemicals. Despite tremendous progress in heterogeneous catalysis, the synthesis of these nitrogen‐containing compounds still remains challenging. Here, we report an efficient, simple, and cost‐effective nitrogen‐doped CeO2‐supported Co single‐atom catalyst (SAC) (Co/N‐CeO2) enabled synthesis of acetamides, benzimidazoles, and benzothiazoles. As far as we know, this is the first to report that SACs catalyze the synthesis of acetamides, benzimidazoles, and benzothiazoles. Detailed spectroscopic characterization revealed the structure of catalytic center. Harnessing the catalytic activity of SACs, the work offers promising routes for future synthesis of heterocycles.

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Selective N-acetylation of aromatic amines using acetonitrile as acylating agent

Cited by 33 publications

References 39 publications

Eco-Friendly, Catalyst and Solvent-Free, Synthesis of Acetanilides and N-Benzothiazole-2-yl-acetamides

Eco-Friendly, Catalyst and Solvent-Free, Synthesis of Acetanilides and N-Benzothiazole-2-yl-acetamides

Lewis‐Acid‐Catalysed Activation of Nitriles: A Microwave‐Assisted Solvent‐Free Synthesis of 2,4‐Disubstituted Quinazolines and 1,3‐Diazaspiro[5.5]undec‐1‐enes

Cobalt Single‐Atom Catalyst: Synthesis, Characterization and Catalytic Activity

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