4411-26-1Relevant articles and documents
Vibrational spectra and molecular structure of isomeric 1-(adamantan-1-ylcarbonyl)-3-(dichlorophenyl)thioureas
Saeed, Aamer,Ashraf, Zaman,Erben, Mauricio F.,Simpson, Jim
, p. 283 - 291 (2017)
1-(adamantan-1-ylcarbonyl)-3-(2,3-dichlorophenyl)thiourea, 1, and 1-(adamantan-1-ylcarbonyl)-3-(2,5-dichlorophenyl)thiourea, 2, were synthesized in reasonable yields from admanantyl-1-carbonyl chloride and ammonium thiocyanate followed by treatment of the resulting adamantane-1-carbonylisothiocyanate with the 2,3- and 2,5-dichloroanilines. A complete vibrational analysis was performed on the basis of FTIR and Raman spectra. The formation of intramolecular N[sbnd]H?O and intermolecular N[sbnd]H?S hydrogen bonds in the solids affect vibrational modes, with low frequency values observed for the ν(C[dbnd]O) and ν(C[dbnd]S) stretching modes. Structural data obtained by single-crystal X-ray diffraction at low temperature confirm this picture. Compound 1 crystallizes in the triclinic system and compound 2 crystallizes with two unique molecules in the asymmetric unit of the orthorhombic unit cell. The molecular structures reveal that the carbonylthiourea units in 1 and both molecules of 2 are planar due in part to the formation of intramolecular N[sbnd]H?O[dbnd]C hydrogen bonds that generate S (6) rings. Moreover, the crystal structures are stabilized by an extensive series of classical and non-classical hydrogen bonds and, in the case of 1 by an intermolecular Cl?Cl halogen bond.
Synthesis of adamantyl-containing isothiocyanates
Burmistrov,Butov,Pitushkin
, p. 1795 - 1796 (2015)
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Adamantane-isothiourea hybrid derivatives: Synthesis, characterization, in vitro antimicrobial, and in vivo hypoglycemic activities
Al-Wahaibi, Lamya H.,Hassan, Hanan M.,Abo-Kamar, Amal M.,Ghabbour, Hazem A.,El-Emam, Ali A.
, (2017)
A new series of adamantane-isothiourea hybrid derivatives, namely 4-arylmethyl (Z)-N1-(adamantan-1-yl)-morpholine-4-carbothioimidates 7a-e and 4-arylmethyl (Z)-N0-(adamantan-1-yl)-4 -phenylpiperazine-1-carbothioimidates 8a-e were prepared via the reaction of N-(adamantan-1- yl)morpholine-4-carbothioamide 5 and N-(adamantan-1-yl)-4-phenylpiperazine-1-carbothioamide 6 with benzyl or substituted benzyl bromides, in acetone, in the presence of anhydrous potassium carbonate. The structures of the synthesized compounds were confirmed by 1H-NMR, 13C-NMR, electrospray ionization mass spectral (ESI-MS) data, and X-ray crystallographic data. The in vitro antimicrobial activity of the new compounds was determined against certain standard strains of pathogenic bacteria and the yeast-like pathogenic fungus Candida albicans. Compounds 7b, 7d and 7e displayed potent broad-spectrum antibacterial activity, while compounds 7a, 7c, 8b, 8d and 8e were active against the tested Gram-positive bacteria. The in vivo oral hypoglycemic activity of the new compounds was carried on streptozotocin (STZ)-induced diabetic rats. Compounds 7a, 8ab, and 8b produced potent dose-independent reduction of serum glucose levels, compared to the potent hypoglycemic drug gliclazide.
A more sustainable isothiocyanate synthesis by amine catalyzed sulfurization of isocyanides with elemental sulfur
Nickisch,Conen,Gabrielsen,Meier
, p. 3134 - 3142 (2021/01/28)
Isothiocyanates (ITCs) are typically prepared using amines and highly toxic reagents such as thiophosgene, its derivatives, or CS2. In this work, an investigation of a multicomponent reaction (MCR) using isocyanides, elemental sulfur and amines revealed that isocyanides can be converted to isothiocyanates using sulfur and catalytic amounts of amine bases, especially DBU (down to 2 mol%). This new catalytic reaction was optimized in terms of sustainability, especially considering benign solvents such as Cyrene or γ-butyrolactone (GBL) under moderate heating (40 °C). Purification by column chromatography was further optimized to generate less waste by maintaining high purity of the product. Thus, E-factors as low as 0.989 were achieved and the versatility of this straightforward procedure was shown by converting 20 different isocyanides under catalytic conditions, while obtaining moderate to high yields (34-95%). This journal is
Reactions of Cage Substrates with Sulfur Nucleophiles
Klimochkin, Yu. N.,Ivleva,Shiryaev
, p. 355 - 363 (2021/04/14)
Abstract: Reactions of alcohols of the adamantane series and adamantan-1-yl nitrates with sulfur nucleophiles in 94% sulfuric acid afforded a number of new sulfur-containing adamantane derivatives such as carbamo-thioates, isothiocyanates, and carbamodithioates. Di(adamantan-1-yl) disulfide was synthesized by reaction of admantan-1-yl nitrate with sodium sulfide nonahydrate in 94% sulfuric acid.
