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Facile Synthesis of Pyrazole-And Benzotriazole-Containing

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Facile Synthesis of Pyrazole-And Benzotriazole-Containing Hindawi Publishing Corporation e Scientific World Journal Volume 2014, Article ID 578762, 5 pages http://dx.doi.org/10.1155/2014/578762 Research Article Facile Synthesis of Pyrazole- and Benzotriazole-Containing Selenoethers Andrei S. Potapov,1,2 Nina P. Chernova,2 Vladimir D. Ogorodnikov,3 Tatiana V. Petrenko,3 and Andrei I. Khlebnikov1,2 1 Department of Biotechnology and Organic Chemistry, National Research Tomsk Polytechnic University, 30 Lenin Avenue, Tomsk 634050, Russia 2 Department of Chemistry, Altai State Technical University, 46 Lenin Avenue, Barnaul 656038, Russia 3 Institute of Petroleum Chemistry, Siberian Branch of Russian Academy of Sciences, 3 Akademicheskii Avenue, Tomsk 634055, Russia Correspondence should be addressed to Andrei S. Potapov; [email protected] Received 8 September 2014; Accepted 4 November 2014; Published 20 November 2014 Academic Editor: Georgiy B. Shul’pin Copyright © 2014 Andrei S. Potapov et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. Azole-containing selenoethers, 1,5-bis(3,5-dimethylpyrazol-1-yl)-3-selena pentane and 1,3-bis(1,2,3-benzotriazol-1-yl)-2-selena propane were prepared by the reaction of corresponding tosylate or chloride with sodium selenide generated in situ from elemental selenium and sodium formaldehydesulfoxylate (rongalite). 1. Introduction NaOH [12], liquid ammonia and sodium [13], sodium in DMF [14], and sodium formaldehydesulfoxylate (rongalite) Organoselenium compounds find applications due to their [15] were reported as sources of selenide ions. Other selenium biological activity and useful synthetic properties (see [1, compounds, such as selenium dioxide (reduced by trialkyl 2] and references cited therein). Selenoethers demonstrate borohydrides) [16] or selenium tetrachloride [17], are less potent ligating ability towards transition and main-group commonly used. elements [3]. On the other hand, azole-containing thioethers Herein we report improved methods for the preparation arealsoknownfortheirrichcoordinationchemistry[4]. of pyrazole- and benzotriazole-containing selenoethers 1,5- Therefore, ligands carrying both azole- and selenoether moi- bis(3,5-dimethylpyrazol-1-yl)-3-selena pentane (2) and 1,3- eties are especially interesting in view of their coordination bis(1,2,3-benzotriazol-1-yl)-2-selena propane (4). chemistry. Nevertheless, only a few reports on compounds of this type have appeared in literature, demonstrating their use as building blocks for supramolecular architecture [5]andas 2. Results and Discussion ligands for catalysts [6–9]. Hodage et al. demonstrated poten- tial glutathione peroxidase-like activity of some pyrazole- 2.1. Synthesis of Selenoethers. In our preparation of azole- containing selenoethers [10]. Recently, Pop et al. prepared a containing selenoethers we used elemental selenium and series of late transition metal complexes of pyrazole-derived sodium formaldehydesulfoxylate (HOCH2SO2Na, rongalite) selenoethers [11]. in aqueous NaOH [18]. The generated in situ sodium selenide Dialkyl selenides (selenoethers) are usually prepared 2− was introduced into the reaction with 1-(2-tosyloxy ethyl)- from alkyl halides and Se species, generated from various 3,5-dimethylpyrazole (1) or 1-chloromethyl benzotriazole (3) selenium compounds. Since selenide ions are very unstable (Scheme 1). Due to low solubility of compound 3 in water towards oxygen, they are generated in situ using different acetonitrile was added to the reaction mixture in order to reducing agents. Selenium in combination with aqueous expedite the nucleophilic substitution. It should be noted that 2 The Scientific World Journal N Se, NaOH, H2O N N HOCH SO Na N OTs 2 2 N Se N 12 N N N N N Se, NaOH, H2O N HOCH SO Na N N 2 2 Se N MeCN Cl 34 Scheme 1: Synthesis of azole-selenoethers. we found it unnecessary to carry out the reactions under C7 C14 nitrogen atmosphere, which is probably due to reductive Se1 C6 atmosphere created by SO2 evolution from the excess of ron- C13 C9 C16 galite. Pyrazole- and benzotriazole-containing selenoethers O5 2 4 N3 ( and )wereobtainedingoodyields(76and90%)asoff- C5 N1 C12 white air- and moisture-stable solids even in the absence of N6 O6 nitrogen atmosphere. It should be noted that in our synthetic N2 Cu1 N4 C11 procedure selenide ions were generated using inexpensive C4 C10 O2 O4 and stable rongalite in contrast to superhydride (LiBEt3H) or C3 NaBH4 used in previously reported methods of preparation N5 C15 of selenoethers 2 [10]and4 [19]. The structures of sele- O1 C8 noethers were confirmed by IR and NMR spectroscopy and, O3 in case of selenoether 2, electron-impact mass-spectrometry. It is known [20] that upon reduction selenium can form 2− 2− Figure 1: Molecular structure of compound 5.Thermalellipsoidsfor diselenide ions Se2 in addition to selenides Se . Therefore, nonhydrogen atoms are drawn at 50% probability level. Hydrogen not only selenoethers, but also diselenides can form as a result atoms are omitted for clarity. of reactions in Scheme 1,andIRandNMRspectroscopyalone do not allow to unambiguously discern between them. bonds (1.95-1.96 A)˚ are also common for acyclic selenoethers [22]. 2.2. X-Ray Crystal Structure Determination. In order to Reports on the synthesis and crystal structure of establish the structures of compounds 2 and 4 we have carried benzotriazole-containing selenoether 4 have appeared in two out single crystal X-ray structure determinations. Single recent papers. Lu et al. [23] used a nucleophilic substitution crystals of compound 4 were obtained by crystallization from reaction of pure sodium selenide with chloro-derivative 2 acetonitrile. Compound 2 hasarelativelylowmeltingpoint to prepare the selenoether in 55% yield. Das et al. [19] andcrystallizedrapidlyfromvarioussolvents,preventing improved the yield up to 78% by generating Na2Se in the formation of single crystals. However, with copper(II) situ from selenium and sodium borohydride. Both papers 2 report crystal structures of prepared selenoethers, which they nitrate compound readily gave well-formed crystals of ∘ complex suitable for X-ray structure determination. The describe as pale-yellow crystals (m.p. 140 C[19]), readily complex [Cu(2)(NO3)2](5) was obtained in high yield (84%); soluble in common organic solvents. Both products appear therefore selenoether 2 and not some other impurity acted as tobethesamemonoselenide,andtheslightdifferencesin aligandandthestructureofthecomplexcanbeusedforthe crystal structures are probably due to unlike packing fashion elucidation of compound 2 structure. of formula units in elementary cells (monoclinic crystal Complex 5 crystallizes in a monoclinic crystal system; system). crystallographic parameters and details of the diffraction The crystallographic parameters, bond lengths, and experiment are given in Table 1.Molecularstructureofthe angles for compound 4 are given in Tables 1 and 2.Theasym- complex is shown in Figure 1, and selected bond lengths and metric unit of this compound is a monoselenide (Figure 2), angles are listed in Table 2.Fromthestructureofcomplex5 it and the elementary cell contains four such units. The molecu- is evident that compound 2 is indeed a selenoether and not a lar structure of selenoether 4 is very similar to those reported diselenide. The lengths of C–C and C–N bonds in pyrazole byDasetal.andLuetal.[19, 23]. The lengths of Se–C bonds rings are within the usual range [21]. The lengths of Se–C are slightly (by 0.01 A)˚ longer than in previously reported The Scientific World Journal 3 ∘ Table 1: Crystallographic data, details of data collection, and Table2:Selectedbonddistances(A)˚ and angles ( )forcompounds structure refinement parameters for compounds 4 and 5. 4 and 5. Example 45 Compound 4 Chemical formula C14H12N6Se C14H22CuN6O6Se Se(1)–C(1A) 1.960(2) N(1A)–C(1A)–Se(1) 112.83(14) −1 M(gmol ) 343.26 512.88 Se(1)–C(1) 1.962(2) C(1A)–Se(1)–C(1) 95.88(9) Temperature (K) 100(2) 100(2) N(1)–C(1) 1.440(3) N(1)–C(1)–Se(1) 111.81(13) Wavelength (A)˚ 0.71073 0.71073 N(1A)–C(1A) 1.441(3) Crystal size (mm) 0.14 × 0.11 × 0.11 0.14 × 0.11 × 0.11 Compound 5 Crystal system Monoclinic Monoclinic Se(1)–C(7) 1.955(3) C(7)–Se(1)–C(14) 99.87(12) Space group P 21/c P 21/c Se(1)–C(14) 1.965(3) C(7)–Se(1)–Cu(1) 101.55(8) (A)˚ 11.2605(8) 16.8873(9) Se(1)–Cu(1) 2.5110(4) C(14)–Se(1)–Cu(1) 100.47(8) (A)˚ 9.1443(7) 8.3578(5) Cu(1)–N(4) 1.965(2) N(4)–Cu(1)–N(2) 175.68(9) (A)˚ 13.6312(10) 13.9597(8) ∘ Cu(1)–N(2) 1.971(2) N(4)–Cu(1)–O(1) 88.00(8) ( )9090 ∘ Cu(1)–O(1) 2.0504(19) N(4)–Cu(1)–Se(1) 87.11(6) ( ) 102.2002(13) 103.2610(10) ∘ Cu(1)–O(4) 2.2700(19) N(2)–Cu(1)–Se(1) 95.72(6) ( )9090 (A˚ 3) 1371.90(18) 1917.74(19) C6 44 C7 −3 Se1 calc (g cm )1.6621.776 −1 C6A C7A (mm )2.7403.082 C1 C2 (0 0 0) C5A C5 688 1036 C2A C1A N1 range for data N1A ∘ 1.85 to 29.00 2.48 to 29.00 collection ( ) C4 −15 ≤ ℎ ≤ 15 −23 ≤ ℎ ≤ 23 C4A N2 C3 C3A N2A N3 Index ranges −12 ≤ ≤ 12 −11 ≤ ≤11 N3A −18 ≤ ≤ 18 −19 ≤ ≤19 4 Reflections collected 15771 22301 Figure 2: Molecular structure of selenoether . Thermal ellipsoids 3651 5086 for nonhydrogen atoms are drawn at 50% probability level. Hydro- Independent reflections [(int) = 0.0446] [(int) = 0.0661] gen atoms are omitted for clarity. Completeness to 2 (%) 99.9 99.7 Semi-empirical Semi-empirical Absorption correction a from equivalents from equivalents Max. and min. 0.753 and 0.700 0.913 and 0.694 transmission Data/restraints/parameters 3651/0/190 5086/0/257 2 Goodness-of-fit on 1.002 1.018 1 = 0.0276 1 = 0.0351 Final 1,2 [ > 2()] 2 = 0.0575 2 = 0.0677 1 = 0.0449 1 = 0.0572 1,2 (all data) 2 = 0.0643 2 = 0.0766 Largest difference in peak −3 0.434 and −0.433 0.590 and −0.604 and hole (e A˚ ) O c b structures, while C–Se–C angle is slightly sharper.
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