A facile IL–DMSO assisted synthesis of 5-, 6-, and 7-membered benzo-annelated cyclic guanidines

Novel 2-Aminobenzamides as Potential Orally Active Antithrombotic Agents

“…So, increasing the temperature of the reaction mixture as a means of decreasing the reaction time was ruled out. Previously, 12 we have used a mixture of ionic liquid:dimethylsulfoxide (IL:DMSO) (1:10) successfully as the solvent for nucleophilic substitution at an activated carbon. We thought of exploring this green and simple protocol for the above said reaction on substituted isatoic anhydrides (7).…”

Guanidines from ‘toxic substances’ to compounds with multiple biological applications – Detailed outlook on synthetic procedures employed for the synthesis of guanidines

“…Microwave-assisted synthesis of highly functionalized guanidines on soluble polymer support © 2012 Elsevier Ltd. 51 Synthesis of novel functionalized guanidines and their different reactions have also been extensively carried out by many research groups, employing different approaches. Including the synthesis of dicarbethoxyguanidine, [103] nitroguanidine, [104] nitrotriarylguanidines, [105] N 1 -(6 -Methoxy-8-quinolylaminoalkyl-)guanidines, [106] 1-(Alky1amino)-guanidines, [107] N-alkyl-N'-carboalkoxy guanidines, [108] guanidino diesters, [109] N-guanidino-modified arginines, [110] radioabeled guanidines, [111] pyranosyl nucleosides with guanidine functionality, [112] phosphinyl guanidines, [113] guanidinium chlorides, [114] phase transfer catalyzed alkylation of guanidines, [115] N-triflyl guanidines, [116] cyclic guanidines, [117], [70] monocyclic guanidines, [118] bicyclic guanidines, [25], [119] tricyclic guanidines, [120] tetracyclic guanidines, [121] macrocyclic guanidines, [122] and polycyclic guanidines. [123] …”

Palladium-Catalyzed Ortho-Selective C–H Oxidative Carbonylation of N-Substituted Anilines with CO and Primary Amines for the Synthesis of o-Aminobenzamides

“…In addition, they also find utilization in medicinal chemistry due to their biological activities such as antimicrobial activity, antithrombotic activity, glycogen phosphorylase inhibition, and thyroid-stimulating hormone receptor (TSHR) antagonistic activity . The main methods for the synthesis of these compounds involve the ring opening of isatoic anhydride, , coupling of anthranilic acid with amines, , N -arylation between 2-bromobenzenamine and benzonitrile, the amidation of alcohols with 2-aminobenzonitrile, or N -Fries rearrangement of N -carbamoyldiarylamines . However, these methods generally suffer from limitations such synthetic precursors that are not easily accessible, low atom economy, and sometimes substrate generality.…”