Zinc(II)-Catalyzed Synthesis of Secondary Amides from Ketones via Beckmann Rearrangement Using Hydroxylamine-O-sulfonic Acid in Aqueous Media

Verma, Saumya; Kumar, Puneet; Khatana, Anil Kumar; Chandra, Dinesh; Yadav, Ajay; Tiwari, Bhoopendra; Jat, Jawahar L.

doi:10.1055/s-0040-1707809

Cited by 9 publications

(4 citation statements)

References 9 publications

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“… Amine Carboxylic acid Product Time (min) Yield a (%) M.p. °C (Lit) 30 87 53 (48–51) 90 30 81 116 (114–116) 94 30 67 171 (169.2–170.8) 95 30 81 186 (182–187) 93 30 74 69 (65.2–67) 95 30 83 105 (103–105) 84 …”

Section: Resultsmentioning

confidence: 99%

Direct additive-free N-formylation and N-acylation of anilines and synthesis of urea derivatives using green, efficient, and reusable deep eutectic solvent ([ChCl][ZnCl2]2)

Abbasi,

Sardarian

2024

Sci Rep

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In the current report, we introduce a simple, mild efficient and green protocol for N-formylation and N-acetylation of anilines using formamide, formic acid, and acetic acid as inexpensive, nontoxic, and easily available starting materials just with heating along stirring in [ChCl][ZnCl2]2 as a durable, reusable deep eutectic solvent (DES), which acts as a dual catalyst and solvent system to produce a wide range of formanilides and acetanilides. Also, a variety of unsymmetrical urea derivatives were synthesized by the reaction of phenyl isocyanate with a range of amine compounds using this benign DES in high to excellent yields. [ChCl][ZnCl2]2 showed good recycling and reusability up to four runs without considerable loss of its catalytic activity.

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Section: Resultsmentioning

confidence: 99%

Direct additive-free N-formylation and N-acylation of anilines and synthesis of urea derivatives using green, efficient, and reusable deep eutectic solvent ([ChCl][ZnCl2]2)

Abbasi,

Sardarian

2024

Sci Rep

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“…Only cyclic ketones were suitable for this procedure, which needed to be carried out under reflux conditions with a very acidic solvent. [135] The amides were produced with an excellent 96 % yield by using ZnCl 2 . (Scheme 100).…”

Section: Zinc (Ii)-catalyst For Direct Conversion Of the Ketone To Amidementioning

confidence: 99%

“…Ketones, a Zn(II) catalyst, and HOSA (nitrogen supply) were combined to create secondary amides in a single step. Only cyclic ketones were suitable for this procedure, which needed to be carried out under reflux conditions with a very acidic solvent [135] . The amides were produced with an excellent 96 % yield by using ZnCl 2 .…”

Section: Miscellaneousmentioning

confidence: 99%

Comprehensive updates on Beckmann Rearrangement

Kaushik,

Jain,

Malik

et al. 2024

ChemistrySelect

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Beckmann rearrangement has been quite successful in the preparation of many medicinally potent scaffolds. In synthetic organic chemistry, the Beckmann rearrangement is quite popular, caprolactam is synthesized from cyclohexanone oxime on a large scale for Nylon‐6 production. The function of numerous catalysts and media in the Beckmann rearrangement has been discussed in depth in this review. In the last 20 years, Beckmann rearrangement catalysis has evolved from a potentially hazardous to a more environmentally friendly catalyst, as a result of greater usage. Catalytic performance and synthetic performance of various catalytic systems have been re‐evaluated in the present review article.

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“…The Beckmann rearrangement has recently emerged as an efficient method for the preparation of amides from ketones . Despite tremendous progress in this direction, α,β-unsaturated ketones have remained elusive for this fundamental transformation to produce acrylamides due to several inherent competing reactivity challenges, such as 1,2-addition, , aza-Michael reaction, , aziridination, and harsh reaction conditions for the in situ generation of oxime intermediates .…”

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confidence: 99%

Amidation of Enones via Beckmann Rearrangement

Verma,

Singh,

Jat

et al. 2024

J. Org. Chem.

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The Beckmann reaction is one of the most atom-economical methods for the preparation of amides from ketones. Unlike ketones, the multiple competing reactivities of enones as well as the requirement of demanding reaction conditions for in situ generation of oximes have severely impacted the application of this reaction for the preparation of α,β-unsaturated amides. Herein, we describe the first chemoselective method for the direct conversion of enones to the corresponding α,β-unsaturated amides using N-Boc-O-tosylhydroxylamine.

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Zinc(II)-Catalyzed Synthesis of Secondary Amides from Ketones via Beckmann Rearrangement Using Hydroxylamine-O-sulfonic Acid in Aqueous Media

Cited by 9 publications

References 9 publications

Direct additive-free N-formylation and N-acylation of anilines and synthesis of urea derivatives using green, efficient, and reusable deep eutectic solvent ([ChCl][ZnCl2]2)

Direct additive-free N-formylation and N-acylation of anilines and synthesis of urea derivatives using green, efficient, and reusable deep eutectic solvent ([ChCl][ZnCl2]2)

Comprehensive updates on Beckmann Rearrangement

Amidation of Enones via Beckmann Rearrangement

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