SHARGHI ET AL.
13 of 14
(
1
1
CDCl , 62.9 MHz, δ, ppm): 51.31, 66.93, 117.01, 123.74,
Y. Yang, Y. Rao, Chem. Commun. 2011, 47, 10133; d) D. H. R.
Bartona, J.‐P. Fineta, J. Khamsia, Tetrahedron Lett. 1988, 29,
1115; e) F. Chen, N. Liu, E. Jia, B. Dai, RSC Adv. 2015, 5,
3
25.56, 125.93, 127.96, 128.19, 130.98, 140.03, 147.08,
−1
58.13. IR (KBr, cm ): 601 (m), 621 (m), 703 (m), 724
5
1512; f) K. R. Reddy, N. S. Kumar, B. Sreedhar, M. L. Kantam,
(w), 752 (s), 785 (s), 812 (s), 879 (m), 863 (m), 925 (s),
J. Mol. Catal. A 2006, 252, 136; g) Z.‐L. Xu, H.‐X. Li, Z.‐G.
Ren, W.‐Y. Du, W.‐C. Xu, J.‐P. Lang, Tetrahedron 2011, 67,
9
1
40 (m), 954 (m), 1039 (m), 1056 (m), 1065 (m), 1118 (s),
147 (m), 1205 (w), 1226 (s), 1257 (m), 1298 (m), 1321
5
282; h) S. M. Islam, S. Mondal, P. Mondal, A. S. Roy, K. Tuhina,
(
2
m), 1361 (s), 1410 (w), 1432 (w), 1599 (m), 1616 (m),
M. Mobarok, Inorg. Chem. Commun. 2011, 14, 1352; i) R. Sridhar,
M. Yedukondalu, N. Chandrasekhar, M. V. Basaveswara Rao, Am.
J. Mater. Sci. 2011, 1, 98; j) H. Chen, D. Wang, X. Wang, W.
Huang, Q. Cai, K. Ding, Synthesis 2010, 9, 1505.
833 (m), 2852 (m), 2959 (m). Anal. Calcd for C H ClN O
2
0
17
4
(364.83) (%): C, 65.84; H, 4.70; N, 15.36. Found (%): C,
6
5.91; H, 4.68; N, 15.09.
[
2] a) M. A. P. Martins, C. P. Frizzo, D. N. Moreira, L. Buriol, P.
Machado, Chem. Rev. 2009, 109, 4140; b) E. C. Gaudino, D.
Carnaroglio, K. Martina, G. Palmisano, A. Penoni, G. Cravotto,
Org. Process Res. Dev. 2015, 19, 499; c) K. Tanaka, Solvent‐Free
Organic Synthesis, 2nd ed., Wiley‐VCH, Weinheim 2009; d) M.
Bakherad, A. Keivanloo, S. Samangooei, Tetrahedron Lett. 2012,
4
.4.9 | 4‐(1H–benzo[d]imidazol‐2‐yl)tetrazolo
[
1,5‐a]quinoline
1
Yellow solid; m.p. 277–280 °C. H NMR (CDCl , 250 MHz,
3
δ, ppm): 7.25–7.39 (m, 2H), 7.58–7.61 (m, 1H), 7.73–7.85 (m,
5
3, 5773; e) A. F. Asachenko, K. R. Sorochkina, P. B. Dzhevakov,
M. A. Topchiy, M. S. Nechaev, Adv. Synth. Catal. 2013, 355, 3553.
[3] D. W. Old, M. C. Harris, S. L. Buchwald, Org. Lett. 2000, 2, 1403.
2
1
1
H), 7.88–7.96 (m, 1H), 8.09 (d, J = 7.5, 1H), 9.07 (s, 1H),
13
1.76 (s, 1 H). C NMR (CDCl , 62.9 MHz, δ, ppm):
3
11.8, 116.9, 119.7, 123.14, 124.4, 128.8, 130.0, 132.1. IR
[
4] B. Y.‐H. Tana, Y.‐C. Teo, Org. Biomol. Chem. 2014, 12, 7478.
−
1
(KBr, cm ): 477 (s), 504 (w), 633 (s), 664 (m), 712 (m),
[
5] S. S. Kampmann, A. N. Sobolev, G. A. Koutsantonis, S. G. Stewart,
Adv. Synth. Catal. 2014, 356, 1967.
7
1
56 (s), 913 (s), 961 (m), 1008 (m), 1097 (m), 1141 (m),
161 (m), 1193 (m), 1208 (m), 1231 (m), 1257 (m), 1285
[
6] a) S. Díez‐González, Catal. Sci. Technol. 2011, 1, 166; b) A. K.
Verma, J. Singh, R. C. Larock, Tetrahedron 2009, 65, 8434; c)
Y.‐Z. Huang, J. Gao, H. Ma, H. Miao, J. Xu, Tetrahedron Lett.
2008, 49, 948; d) F. Xue, C. Cai, H. Sun, Q. Shen, J. Rui, Tetrahe-
dron Lett. 2008, 49, 4386; e) A. K. Verma, J. Singh, V. K. Sankar,
R. Chaudhary, R. Chandra, Tetrahedron Lett. 2007, 48, 4207; f) S.
Haneda, Y. Adachi, M. Hayashi, Tetrahedron 2009, 65, 10459;
g) Z. Xi, F. Liu, Y. Zhou, W. Chen, Tetrahedron 2008, 64, 4254;
h) D. K. T. Yadav, S. S. Rajak, B. M. Bhanage, Tetrahedron Lett.
(
(
(
m), 1314 (s), 1337 (s), 1374 (m), 1410 (s), 1441 (m), 1456
m), 1517 (s), 1544 (s), 1581 (m), 1605 (s), 3064 (m), 3328
s). Anal. Calcd for C H N (286.29) (%): C, 67.12; H,
1
6 10 6
3.52; N, 29.35. Found (%): C, 67.07; H, 3.59; N, 29.50.
4
.4.10 | 4‐(5‐methyl‐1H‐benzo[d]imidazol‐2‐
yl)tetrazolo[1,5‐a]quinoline
2
014, 55, 931; i) N. V. Suramwar, S. R. Thakare, N. N. Karade,
1
Yellow solid; m.p. 241–242 °C. H NMR (CDCl , 250 MHz,
3
N. T. Khaty, J. Mol. Catal. A 2012, 359, 28; j) J. Mao, J. Guo, H.
Song, S.‐J. Ji, Tetrahedron 2008, 64, 1383; k) N. Panda, A. K. Jena,
S. Mohapatra, S. R. Rout, Tetrahedron Lett. 2011, 52, 1924;
l) S. M. Islam, N. Salam, P. Mondal, A. S. Roy, K. Ghosha, K.
Tuhina, J. Mol. Catal. A 2014, 387, 7; m) R. K. Rao, A. B. Naidu,
E. A. Jaseer, G. Sekar, Tetrahedron 2009, 65, 4619; n) H. Yang, C.
Xi, Z. Miao, R. Chen, Eur. J. Org. Chem. 2011, 3353; o) B.
Sreedhar, K. B. S. Kumar, P. Srinivas, V. Balasubrahmanyam, G.
T. Venkanna, J. Mol. Catal. A 2007, 265, 183; p) L. Xin, B.
Weiliang, J. Org. Chem. 2007, 72, 3863; q) H.‐J. Cristau, P. P.
Cellier, J.‐F. Spindler, M. Taillefer, Eur. J. Org. Chem. 2004,
695; r) C.‐A. Jon, K. Artis, L.‐B. Stephen, J. Am. Chem. Soc.
δ, ppm): 2.46 (s, 3H), 7.04 (t, J = 8.0, 1H), 7.26–7.30 (m, 1H),
7
8
.39–7.48 (m, 1H), 7.74 (t, J = 7.5, 1H), 7.89 (t, J = 7.7, 1H),
.06 (d, J = 7.7, 1H), 8.65 (d, J = 8.2, 1H), 8.97 (s, 1H), 11.56
13
(s, 1H). C NMR (CDCl , 62.9 MHz, δ, ppm): 21.83, 111.03,
3
1
1
14.6, 116.7, 119.0, 124.0, 125.0, 125.8, 128.6, 129.8, 130.2,
30.4, 131.7, 134.1, 141.7, 144.7, 145.5. IR (KBr, cm ): 468
−
1
(
(
s), 490 (s), 596 (s), 671 (br), 713 (w), 729 (m), 750 (s), 773
m), 798 (s), 863 (m), 906 (m), 945 (m), 1012 (w), 1100 (s),
1
1
126 (m), 1140 (m), 1212 (s), 1280 (s), 1316 (s), 1337 (m),
398 (m), 1539 (br), 2915 (s), 3255 (s). Anal. Calcd for
2
002, 124, 11684; s) H. Chen, M. Lei, L. Hu, Tetrahedron 2014,
C H N (300.32) (%): C, 67.99; H, 4.03; N, 27.98. Found
1
7 12 6
7
0, 5626; t) Q. Zhang, X. Wang, C. Cheng, R. Zhu, N. Liu, Y.
(%): C, 67.91; H, 4.08; N, 30.02.
Hu, Org. Biomol. Chem. 2012, 10, 2847; u) S. Jindabot, K.
Teerachanan, P. Thongkam, S. Kiatisevi, T. Khamnaen, P.
Phiriyawirut, S. Charoenchaidet, T. Sooksimuang, P. Kongsaeree,
P. Sangtrirutnugul, J. Organometal. Chem. 2014, 750, 35; v) D.
Urankar, B. Pinter, A. Pevec, F. D. Proft, I. Turel, J. K. Smrlj,
Inorg. Chem. 2010, 49, 4820; w) E. Amadio, A. Scrivanti, M.
Bortoluzzi, M. Bertoldini, V. Beghetto, U. Matteoli, G. Chessa,
Inorg. Chim. Acta 2013, 405, 188.
ACKNOWLEDGEMENT
We gratefully acknowledge the support of this work by the
Shiraz University Research Council.
REFERENCES
[
7] J. Hu, Y. Cheng, Y. Yang, Y. Rao, Chem. Commun. 2011, 47,
1
0133.
[1] a) D. S. Surry, S. L. Buchwald, Chem. Sci. 2010, 1, 13; b) H.
Sharghi, P. Shiri, Synthesis 2015, 47, 1131; c) J. Hu, Y. Cheng,
[8] N. E. Genung, L. Wei, G. E. Aspnes, Org. Lett. 2014, 16, 3114.