Environmentally benign decarboxylative N-, O-, and S-acetylations and acylations

Abstract

A general method for N-, O- and S-acetylation and acylation using Meldrum's acid and its derivatives has been developed.

Amine-Induced Selective C–C Bond Cleavage of 2,2,2-Trifluoroethyl Carbonyls for the Synthesis of Ureas and Amides

“…also consistent with the results in Scheme 4. Importantly, by adding 5.0 equiv of O 18 -labeled water to the reaction, we confirmed that the oxygen atom in the alkylamide moiety ( 13) originated from trace amounts of water in the solvent (Scheme 5e). 16 Although the exact mechanism of the present C−C bond cleavage of 2,2,2-trifluoroethyl carbonyls remained elusive, based on the experimental results and literature reports, 12e,12 we proposed the possible reaction pathways as following (Scheme 6).…”

“…Isolated by column chromatography on silica gel (PE/EA = 2:1, R f = 0.6); white solid; 1 H NMR (400 MHz, CDCl 3 , ppm) δ 7.39 (d, J = 7.7 Hz, 2H), 7.28 (t, J = 7.6 Hz, 2H), 7.03 (t, J = 7.4 Hz, 1H), 6.45 (br, 1H), 3.02 (s, 6H); 13 C{ 1 H} NMR (100 MHz, CDCl 3 ) δ 155.8, 139.3, 128.8, 122.9, 119.9, 36.4 5, 137.9, 128.7, 127.8, 121.1, 36.4; HRMS (ESI) calcd for C 9 H 12 ClN 2 O [M + H + ], 199.0633;ethan-1-one (12). 18 (18 mg, 79%). Isolated by column chromatography on silica gel (PE/EA = 1:1, R f = 0.3); yellow oil; 1 H NMR (600 MHz, CDCl 3 , ppm) δ 3.47−3.42 (m, 4H), 2.06 (s, 3H), 1.99−1.95 (m, 2H), 1.90−1.85 (m, 2H); 13 C{ 1 H} NMR (150 MHz,CDCl 3 ) δ 169.0,47.3,45.4,26.0,24.5,22.4.…”

Sustainable production of active pharmaceutical ingredients from lignin-based benzoic acid derivatives via “demand orientation”

“…Finally, 4-acetamidophenol was obtained by the acylation of p-aminophenol with acetyl chloride, 146 acetic acid, 147 acetamide, 148 or other reagents. [149][150][151] Compared with the conventional 4-acetamidophenol synthesis process, the route maximizes utilization of the structure of the H-type lignin and has the advantage of a shorter synthesis route and easier availability of raw materials.…”

“…11 (a) Traditional petrochemical, (b) green petrochemical, and (c) potential sustainable routes for paracetamol production. [138][139][140][141][142][143][144][145][146][147][148][149][150][151] procaine solution (0.2%) has an antibacterial effect, inhibiting the growth and even eliminating dozens of colonies, such as Staphylococcus aureus, Acanthamoeba, and Proteus mirabilis. [157][158][159] A conventional route for the synthesis of oxybuprocaine is shown in Fig.…”

Site-Selective Deoxygenative Amination of Azine N-Oxides with Carbodiimides under Catalyst-, Activator-, Base-, and Solvent-Free Conditions

“…There were no byproducts, and only volatile CO 2 was formed as a co-product, which can be separated easily. Furthermore, the evolved CO 2 was trapped efficiently as a bench-stable ammonium carbamate salt 9 (Scheme S2, see SI), and this can be utilized as a reagent and catalyst for different organic transformations . Taken together, the present method is superior to all known methods in the context of reduction of undesired chemical waste and increase of atom economy.…”