52298-91-6Relevant articles and documents
Changes in the conformational parameters of 1-allylbenzotriazole in a mixed halide π-complex [CuCl0.85Br0.15(C6H 4N3CH2CH=CH2)] under the action of bromine atoms
Goreshnik,Mykhalichko,Davydov
, p. 172 - 176 (2005)
Single crystals of [CuCl0.85Br0.15(C 6H4N3CH2=CH2)] (I) were obtained by alternating current electrochemical synthesis; their X-ray structural investigation has been carried out (DARCh automatic diffractometer, MoK α radiation, θ/2θ scanning; 1460 reflections with F ≥ 4σ(F), R = 0.0517). The crystals are monoclinic, their space group is P21/c, a = 7.292(3) A, b = 17.947(8) A, c = 7.398(4) A, β = 93.56(4)°, V = 966(1) A3, Z = 4). Complex I is close in structure to the previously investigated compound [CuCl(C6H4N3CH2=CH2)] (II). In both structures, the trigonal-pyramidal surroundings of the copper atom include two halide atoms (one is apical), a nitrogen atom, and a C=C group. The Cu2X2 dimers are associated into {[Cu2X 2(C6H5N3CH2=CH 2)]}n layers due to the bridging function of the 1-allylbenzotriazole molecule. In spite of the similar coordination polyhedra of the metal atoms and identical bridging function of the ligand molecule in I and II, the differences in the conformation parameters of the allyl group π-coordinated by the copper(I) atom (trans-like in I and cis-like in II) caused by the presence of bromine atoms in the coordination sphere predetermine different structures of the organometallic [Cu2X2(C 6H5N3CH2=CH2)] 4 tetramer subunits in the layers and, as a consequence, formation of different crystal structures.
Synthesis of Structurally Diverse Benzotriazoles via Rapid Diazotization and Intramolecular Cyclization of 1,2-Aryldiamines
Faggyas, Réka J.,Sloan, Nikki L.,Buijs, Ned,Sutherland, Andrew
, p. 5344 - 5353 (2019/05/21)
An operationally simple method has been developed for the preparation of N-unsubstituted benzotriazoles by diazotization and intramolecular cyclization of a wide range of 1,2-aryldiamines under mild conditions, using a polymer-supported nitrite reagent and p-tosic acid. The functional group tolerance of this approach was further demonstrated with effective activation and cyclization of N-alkyl, -aryl, and -acyl ortho-aminoanilines leading to the synthesis of N1-substituted benzotriazoles. The synthetic utility of this one-pot heterocyclization process was exemplified with the preparation of a number of biologically and medicinally important benzotriazole scaffolds, including an α-amino acid analogue.
Isomer-selective complexation of copper(I) ionic salts towards 1- and 2-allylbenzotriazoles. Synthesis and characterization of CuBF 4·2-all-bta·H2O, CuClO4·2- all-bta, CuClO4·1-all-bta·2-all-bta and CuHSO 4·2-all-bta - The first known example of CuHSO4 π-complexes
Goreshnik,Vakulka,Slyvka, Yu. I.,Mys'Kiv
experimental part, p. 1 - 5 (2012/06/29)
The alternating current electrochemical synthesis starting from ethanol solution of Cu(ClO4)2·6H2O, CuSO 4·5H2O and Cu(BF4)2· 6H2O with the equimolar mixture of 1- and 2-allylbenzotriazole (all-bta) has led to a formation of Cu[2-all-bta]ClO4 (I), Cu[2-all-bta]HSO4 (II) and Cu[2-all-bta]BF4·H 2O (III) compounds. The direct interaction between Cu(ClO 4)2·6H2O and the mixture of 1- and 2-allylbenzotriazole in ethanol solution results in an appearance of Cu[(1-all-bta)(2-all-bta)]ClO4 (IV) compound. These results are strikingly different from earlier performed syntheses using the same ligands mixture and copper(II) halides, and producing coordination compounds with 1-allylbenzotriazole only. Compounds I and II are isotypical and crystallize in a monoclinic space group Cc. I: a = 9.5413(10) , b = 12.3171(9) , c = 10.3264(10) , β = 111.155(4)°, V = 1131.78(18) 3, Z = 4. II: a = 9.1707(17) , b = 13.6639(17) , c = 9.4543(17) , β = 105.555(7)°, V = 1141.3(3) 3, Z = 4. The main feature of structures I and II is a chelate-bridging role of the ligand moiety, bonded to one copper ion via CC-bond of the allyl group and nitrogen atom of the triazole core, and to the second Cu+ centre by another N atom. Trigonal-pyramidal copper environment comprises of two nitrogen atoms from different ligand units, CC-bond and oxygen atom at the apical position. The bridging function of both Cu+ cations and 2-all-bta molecules results in the formation of infinite chains. High affinity of BF4- anion to the H2O leads to a formation of compound III including water molecule. It crystallizes in an orthorhombic Pbca space group, a = 13.502(8) b = 11.299(5) c = 16.124(8) , V = 2460(2) 3, Z = 8. The ligand moiety plays the same as in I and II chelate-bridging function, but Cu+, being also bonded to CC group and to two N atoms, is connected with the disordered BF4- anion through the water bridge. In the crystal structure IV the metal ion possesses mixed-isomer surrounding, being bound to N-atom and CC-bond of 2-all-bta molecule, N-atom of 1-all-bta-moiety and O(ClO4 -) atom at apical position. IR spectra confirm rather effective Cu-(CC) bonding.
