One-Pot Parallel Synthesis of 5-(Dialkylamino)tetrazoles.

Two protocols for the combinatorial synthesis of 5-(dialkylamino)tetrazoles were developed. The best success rate (67%) was shown by the method that used primary and secondary amines, 2,2,2-trifluoroethylthiocarbamate, and sodium azide as the starting reagents. The key steps included the formation of unsymmetrical thiourea, subsequent alkylation with 1,3-propane sultone and cyclization with azide anion. A 559-member aminotetrazole library was synthesized by this approach; the overall readily accessible (REAL) chemical space covered by the method exceeded 7 million feasible compounds.

Crystal structure of bis-{µ2-3-(pyridin-2-yl)-5-[(1,2,4-triazol-1-yl)meth-yl]-1,2,4-triazolato}bis-[aqua-nitrato-copper(II)] dihydrate.

The structure of the dinuclear title complex, [Cu2(C10H8N7)2(NO3)2(H2O)2]·2H2O, consists of centrosymmetric dimeric units with a copper-copper separation of 4.0408 (3) Å. The Cu(II) ions in the dimer display a distorted octa-hedral coordination geometry and are bridged by two triazole rings, forming an approximately planar Cu2N4 core (r.m.s. deviation = 0.049 Å). In the crystal, O-H⋯O, O-H⋯N and C-H⋯O hydrogen bonds and π-π inter-actions link the mol-ecules into a three-dimensional network.

Crystal structure of aqua-(nitrato-κO)dioxido{2-[3-(pyridin-2-yl-κN)-1H-1,2,4-triazol-5-yl-κN (4)]phenolato-κO}uranium(VI) aceto-nitrile monosolvate monohydrate.

In the title compound, [U(C13H9N4O)(NO3)O2(H2O)]·CH3CN·H2O, the U(VI) atom is seven-coordinated in a distorted penta-gonal-bipyramidal N2O5 manner by one tridentate triazole ligand, one monodentate nitrate anion and one water mol-ecule in the equatorial plane and by two uran-yl(VI) O atoms in the axial positions. In the crystal, the U(VI) complex mol-ecule is linked to the water and aceto-nitrile solvent mol-ecules through N-H⋯N, O-H⋯O and O-H⋯N hydrogen bonds, forming a sheet structure parallel to the bc plane. The sheets are further linked by an additional O-H⋯O hydrogen bond, forming a three-dimensional network.

Crystal structure of C-2-benzo-thia-zole-N-methyl-nitrone.

The mol-ecule of the title compound {systematic name: N-[(benzo-thia-zol-2-yl)methyl-idene]methyl-amine N-oxide}, C9H8N2OS, is close to planar [maximum deviation from the mean plane = 0.081 (2) Å], its conformation being stabilized by a strong intra-molecular attractive S⋯O inter-action [2.6977 (16) Å]. In the crystal, mol-ecules are linked into centrosymmetric dimers by pairs of weak C-H⋯O hydrogen bonds.

2,2,2-Trifluoroethyl Chlorooxoacetate--Universal Reagent for One-Pot Parallel Synthesis of N(1)-Aryl-N(2)-alkyl-Substituted Oxamides.

A one-pot parallel synthesis of N(1)-aryl-N(2)-alkyl-substituted oxamides with 2,2,2-trifluoroethyl chlorooxoacetate was developed. The synthesis of a library of 45 oxamides revealed higher efficiency of this reagent over the known ethyl chlorooxoacetate. The reagent was successfully used to prepare the known oxamide-containing HIV entry inhibitors.

One-Pot Parallel Synthesis of Alkyl Sulfides, Sulfoxides, and Sulfones.

A simple and cost-effective one-pot parallel synthesis approach to sulfides, sulfoxides, and sulfones from thiourea was elaborated. The method combines two procedures optimized to the parallel synthesis conditions: alkylation of thiourea with alkyl chlorides and mono or full oxidation of in situ generated sulfides with H2O2 or H2O2-(NH4)2MoO4. The experimental set up required commonly used lab equipment: conventional oven and ultrasonic bath; the work up includes filtration or extraction with chloroform. The method was evaluated on an 81 member library of drug-like sulfides, sulfoxides, and sulfones yielding the compounds on a 30-300 mg scale. A small-scale synthesis of 2-(benzhydrylsulfinyl)acetamide (modafinil) utilizing our approach resulted in similar efficiency to the published procedures.

Bis(2,2,2-trifluoroethyl) carbonate as a condensing agent in one-pot parallel synthesis of unsymmetrical aliphatic ureas.

One-pot parallel synthesis of unsymmetrical aliphatic ureas was achieved with bis(2,2,2-trifluoroethyl) carbonate. The procedure worked well for both the monosubstituted and functionalized alkyl amines and required no special conditions (temperature control, order, or rate of addition). A library of 96 diverse ureas was easily synthesized.

Bis(methanol-κO)dioxido[3,3'-(1H-1,2,4-triazole-3,5-diyl)diphenolato-κ3O,N4,O']uranium(VI) methanol monosolvate.

The structure of the title compound, [U(C(14)H(9)N(3)O(2))O(2)(CH(3)OH)(2)]·CH(3)OH, is the first to be reported for an actinide complex including triazole ligands. The U(VI) atom exhibits a pentagonal-bipyramidal NO(6) coordination environment, involving two axial oxide ligands [U=O = 1.766 (3) and 1.789 (3) Å], four equatorial O atoms [U-O = 2.269 (3)-2.448 (3) Å] from the ligand and the two coordinated methanol molecules, and one equatorial N atom [U-N = 2.513 (4) Å] from the ligand. In the crystal structure, the complex molecules are linked via intermolecular N-H...O and O-H...O hydrogen bonds to form a two-dimensional structure.