A Novel and Green Method for N-acylation of Amines and Sulfonamides under Ultrasound Irradiation

Abstract

A facile and versatile method for acylation of structurally diverse amines and sulfonamides under focused ultrasonic irradiation in catalyst-free and solvent-free conditions is reported. There are several advantages to this approach such as simple and easier workup conditions, small amount of time and high yielding. The acylation reaction was carried out with acetic anhydride. All structures of synthesized products have been identified by NMR and mass spectroscopy.

Cobalt(II)‐Catalyzed N‐Acylation of Amines through a Transamidation Reaction

“…N ‐(4‐Phenylpiperazin‐1‐yl)acetamide (2ze): Purified by TLC to give 2ze (89 %) as a yellow oil. 1 H NMR (400 MHz, CDCl 3 ): δ = 7.31–7.27 (m, 2 H), 6.94–6.89 (m, 3 H), 3.77 (t, J = 5.2 Hz, 2 H), 3.62 (t, J = 5.2 Hz, 2 H), 3.19–3.13 (m, 4 H), 2.14 (s, 3 H) ppm.…”

“…1 [3,4-Dihydroisoquinolin-2(1H)-yl](phenyl)methanone (2zd): [26] Purified by TLC to give 2zd (32 %) as a yellow oil. 1 [27] Purified by TLC to give 2ze (89 %) as a yellow oil. 1 -N-(naphthalen-1-ylmethyl)acetamide (2zg): [28] Purified by TLC to give 2zg (86 %) as a yellow oil.…”

Ferric Chloride-Mediated Transacylation of N-Acylsulfonamides

“…From benzenemethanesulfonamide (4v, 95% purity, 0.541 g, 3 mmol); white solid; yield: 0.631 g (98%); mp 131−132 °C (lit. 76 N-(tert-Butylsulfonyl)acetamide (3w). From tert-butylsulfonamide (4w, 0.688 g, 5 mmol); purified by recrystallization (EtOAc/hexane); white solid; yield: 0.765 g (85%); mp 123−124 °C (lit.…”

Recent Progress in Synthesis of Sulfonamides and N‐Acylsulfonamides, Biological Applications and Their Structure‐Activity Relationship (SAR) Studies

“…the synthesis of various sulfonamide amino acid (53) and (54). The preparation of N-sulfonylformamidines is reported via the direct condensation of sulfonyl chlorides (50) with p-hydroxybenzoic acid (52) or amino acids (51) in water with Na 2 CO 3 . The sulfonamide derivatives were produced with high yields and purities (Scheme 6).…”

“…A facile and practical procedure for the N-acylation of sulfonamides under focused ultrasonic irradiation in catalystsolvent-free conditions is reported by Bouasla et al. [52] As shown in (Scheme 21), the reaction of parent sulfonamide (119) with acetic anhydride (120) as an acylating agent at room temperature completed at 15-60 min, the acylated products (121) were isolated in good to excellent yields. This methodology provides a green and much improved approach over the classic methods.…”