Practical Synthesis of N-Substituted Cyanamides via Tiemann Rearrangement of Amidoximes

Abstract

A facile and general synthesis of various N-substituted cyanamides was accomplished by the Tiemann rearrangement of amidoximes with benzenesulfonyl chlorides (TsCl or o-NsCl) and DIPEA.

Repression of GSK3 restores NK cell cytotoxicity in AML patients

“…1H NMR (500 MHz, DMSO-d 6 ) δ 9.18 (s, 1H), 7.33 (d, J =8.5 Hz, 2H), 6.51 d, J =8.5 Hz, 2H), 5.50 (s, 2H), 5.24 (s, 2H); 13 C NMR (125 MHz, DMSO-d 6 ) δ 151.1, 149.3, 126.1, 120.4, 112.9; Liquid Chromatography-Mass Spectrometry (LC-MS) ( m/z ): [M] + calcd (for C 7 H 10 N 3 O) 152, found 152. These data are consistent with the literature data for the same compound 52 .…”

TiO2‐Nanoparticles Catalyzed Synthesis of New Trifluoromethyl‐4,5‐dihydro‐1,2,4‐oxadiazoles and Trifluoromethyl‐1,2,4‐oxadiazoles

“…The necessary amidoximes 1 were readily synthesized according to a standard literature protocol in one‐pot way . The reaction of carbonitrile with aqueous hydroxylamine solution in ethanol under reflux conditions provided the desired amidoximes 2 (Scheme ).…”

Recent Advances in Cyanamide Chemistry: Synthesis and Applications

“…In their seminal report, Tiemann detected a series of diverse mixture of products, which included cyanamide, carbodiimide, guanidine and benzimidazole, among others. In 2014 Chien et al revisited this reaction and developed conditions that led to the selective formation of monosubstituted aryl-cyanamide from the corresponding aryl-amidoxime [ 14 ]. Upon treatment with p -TsCl in the presence of DIPEA or pyridine, the amidoximes were converted to cyanamides in good to excellent yields ( Scheme 7 ).…”