Regio-selective synthesis of 5-substituted 1H-tetrazoles using ionic liquid [BMIM]N3 in solvent-free conditions: a click reaction

Research on Chemical Intermediates - Tập 42 Số 3 - Trang 1593-1610 - 2016
Soheila Khaghaninejad1, Majid Μ. Heravi1, Tayebeh Hosseinnejad1, Hossein A. Oskooie1, Mehdi Bakavoli2
1Department of Chemistry, School of Science, Alzahra University, Vanak, Tehran, Iran
2Department of Chemistry, School of Science, Ferdowsi University of Mashhad, Mashhad, Iran

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R.J. Herr, Bioorg. Med. Chem. Lett. 10, 3379 (2002)

H. Xue, Y. Gau, B. Twamley, J.M. Shreeve, Chem. Mater. 17, 191–198 (2005)

P.B. Mohite, V.H. Bhaskar, Int. J. Pharm. Technol. Res 3, 1557 (2011)

J. Sauer, R. Huisgen, H.J. Strum, Tetrahedron 11, 241 (1960)

Z. NorooziTisseh, M. Dabiri, M. Nobahar, A. AbolhasaniSoorki, A. Bazgir, Tetrahedron 68, 3351 (2012)

Z. NorooziTisseh, M. Dabiri, M. Nobahar, H.R. Khavasi, A. Bazgir, Tetrahedron 68, 1769 (2012)

S. Wu, A. Fluxe, J. Sheffer, J.M. Janusz, B.E. Blass, R. White, C. Jackson, R. Hedges, M. Muawsky, B. Fang, G.M. Fadayel, M. Hare, L. Djandjighian, Bioorg. Med. Chem. Lett. 16, 6213 (2006)

K.J. Wirth, T. Paehler, B. Rosenstein, K. Knobloch, T. Maier, J. Frenzel, J. Brendel, A.E. Busch, M. Bleich, Cardiovasc. Res. 60, 298 (2003)

T. Jin, S. Kamijo, Y. Yamamoto, Tetrahedron Lett. 45, 9435 (2004)

J. Braun, W. Keller, BerichteDtsch. Chem. Ges. 65, 1677 (1932)

B. Das, C.R. Reddy, D.N. Kumar, M. Krishnaiah, R. Narender, Synlett 3, 391 (2010)

B. Gutmann, J.P. Roduit, D. Roberge, C.O. Kappe, Angew. Chem. Int. Ed. Engl. 49, 7101 (2010)

J. Bonnamour, C. Bolm, Tetrahedron 15, 4543 (2009)

M. Habibi, Y. Bayat, D. Habibi, S. Moshaee, Tetrahedron Lett. 50, 4435 (2009)

B. Schmidt, D. Meid, D. Kieser, Tetrahedron 63, 492 (2007)

R. Huisgen, Angew. Chem. Int. Ed. Engl. 2, 565 (1963)

R. Huisgen, G. Szeimies, Chem. Ber. 100, 2494 (1967)

H.C. Kolb, K.B. Sharpless, DrugDiscov. Today 8, 1128 (2003)

W.H. Binder, R. Sachsenhofer, Macromol. Rapid Commun. 28, 15 (2007)

Z.P. Demko, K.B. Sharpless, J. Org. Chem. 66, 7945 (2001)

H.C. Kolb, M.G. Finn, K.B. Sharpless, Angew. Chem. Int. Ed. Engl. 40, 2004 (2001)

Y.W. Yao, Y.W. Zhou, B.P. Lin, C. Yao, Tetrahedron Lett. 54, 6779 (2013)

A. LeTiran, J.P. Stables, H. Kohn, Bioorg. Med. Chem. Lett. 9, 2693 (2001)

A.F. Hegarty, N.M. Tynan, S.J. Fergus, Perkin Transit 22, 1328 (2002)

D. Kundu, A. Majee, A. Hajra, Tetrahedron Lett. 50, 2668 (2009)

A.R. Katritzky, C. Cai, N.K. Meher, Synthesis 8, 1204 (2007)

V.S. Patil, K.P. Nandre, A.U. Borse, S.V. Bhosale, Eur. J. Chem. 9, 1145 (2012)

D. Amantini, R. Beleggia, F. Fringuelli, F. Pizzo, L. Vaccaro, J. Org. Chem. 69, 2896 (2004)

V. Aureggi, G. Sedelmeier, Angew. Chem. Int. Ed. 46, 8440 (2007)

V. Rama, K. Kanagaraj, K. Pitchumani, J. Org. Chem. 76, 9090 (2011)

L.V. Myznikov, Y.A. Efimova, T.V. Artamonova, G.I. Koldobskii, Russ. J. Org. Chem. 47, 728 (2011)

B. Sreedhar, A.S. Kumar, D. Yada, Tetrahedron Lett. 52, 3565 (2011)

G. Aridoss, K.K. Laali, Eur. J. Org. Chem. 31, 6343 (2011)

A. Teimouri, A.N. Chermahini, Polyhedron 30, 2606 (2011)

M.A. Epishina, A.S. Kulikov, N.V. Ignat’ev, M. Schulte, N.N. Makhova, Mendeleev. Commun. 21, 334 (2011)

O. Marvi, A. Alizadeh, S. Zarrabi, Korean Chem. Soc. 32, 4001 (2011)

J. Roh, T.V. Artamonova, K. Vavrova, G.I. Koldobskii, A. Hrabalek, Synthesis 13, 2175 (2009)

A.N. Chermahini, A. Teimouri, A. Moaddeli, Heteroat. Chem. 22, 168 (2011)

B.E. Huff, M.A. Staszak, Tetrahedron Lett. 34, 8011 (1993)

S.J. Wittenberger, B.G. Donner, J. Org. Chem. 58, 4139 (1993)

M. Lakshmi Kantam, K.B. Shiva Kumar, C. Sridhar, Adv. Synth. Catal. 347, 1212 (2005)

M. Lakshmi Kantam, V. Balasubrahmanyam, K.B. Shiva Kumar, Synth. Commun. 36, 1809 (2006)

M. Lakshmi Kantam, K.B. Shiva Kumar, K.J. Phani Raja, J. Mol. Catal. A-Chem. 247, 186 (2006)

M.B. Gawande, V.D.B. Bonifacio, R. Luque, P.S. Branco, R.S. Varma, Chemsuschem 7, 24 (2014)

S.J. Zhang, J. Sun, X.C. Zhang, J.Y. Xin, Q.Q. Miao, J.J. Wang, J. Org. Chem. 43, 7838 (2014)

Y. Gu, F. Shi, Y. Deng, J. Org. Chem. 69, 391 (2004)

B.C. Ranu, R. Jana, J. Org. Chem. 70, 8621 (2005)

J.S. Wilkes, J.A. Levisky, R.A. Wilson, C.L. Hussey, Inorg. Chem. 21, 1263 (1982)

T. Qin, X. Li, J. Chen, Y. Zeng, T. Yu, G. Yang, Y. Li, Chem. Asian J. 9, 3641 (2014)

C. Chiappe, C.S. Pomelli, Eur. J. Org. Chem. 28, 6120 (2014)

A. Fazeli, H.A. Oskooie, Y.S. Beheshtiha, M.M. Heravi, H. Valizadeh, Org. Chem. 10, 738 (2013)

A. Fazeli, H.A. Oskooie, Y.S. Beheshtiha, M.M. Heravi, H. Valizadeh, F. Bamoharram, Monatsh. Chem. 144, 1407 (2013)

A. Fazeli, H.A. Oskooie, Y.S. Beheshtiha, M.M. Heravi, F.M. Moghaddam, B.K. Foroushani, Synlett 8, 391 (2013)

M.M. Heravi, A. Fazeli, H.A. Oskooie, H. Valizadeh, Synlett 20, 2927 (2012)

M.M. Heravi, H. Hamidi, V. Zaadsirjan, Curr. Org. Synth. 11, 647 (2014)

M.M. Heravi, E. Hashemi, YSh Beheshtiha, Kh Kamjou, M. Toolabi, N. Hosseintash, J. Mol. Catal. A-Chem. 392, 173 (2014)

M.M. Heravi, H. Alinejhad, Kh Bakhtiari, H.A. Oskooie, Mol. Divers. 14, 621 (2010)

M.M. Heravi, R.H. Shoar, L. Pedram, J. Mol. Catal. A-Chem. 231, 89 (2005)

H.A. Oskooie, Z. Alimohammadi, M.M. Heravi, A. Soorki, A. Bazgir, Heteroat. Chem. 17, 699 (2006)

H.A. Oskooie, M.M. Heravi, A. Sadnia, Chin. Chem. Lett. 18, 1357 (2007)

M.M. Heravi, F.K. Behbahani, V. Zadsirjan, H.A. Oskooie, J. Braz. Chem. Soc. 17, 1045 (2006)

A. Davoodnia, M.M. Heravi, L. Rezaei-Daghigh, N. Tavakoli-Hoseini, Chin. J. Chem. 28, 429 (2010)

A. Davoodnia, M.M. Heravi, Z. Safavi-Rad, N. Tavakoli-Hoseini, Synth. Commun. 40, 2588 (2010)

A. Davoodnia, M.M. Heravi, L. Rezaei-Daghigh, N. Tavakoli-Hoseini, Mon. Chem. 140, 1499 (2009)

L. Chunhua, X. Zhaohui, L. Weilin, Int. J. Org. Chem. 3, 275 (2013)

T. Hosseinnejad, M.M. Heravi, R. Firouzi, J. Mol. Model. 19, 951 (2013)

A.D. Becke, J. Chem. Phys. 98, 1372 (1993)

Y. Zhao, D.G. Truhlar, Theor. Chem. Acc. 120, 215 (2008)

M.W. Schmidt, K.K. Baldridge, J.A. Boatz, S.T. Elbert, M.S. Gordon, J.H. Jensen, S. Koseki, N. Matsunaga, K.A. Nguyen, S.J. Su, T.L. Windus, M. Dupuis, J.A. Montgomery, J. Comput. Chem. 14, 1347 (1993)

R.F.W. Bader, Atoms in Molecules: A Quantum Theory (Oxford University Press, Oxford, 1990)

R.G.A. Bone, R.F.W. Bader, J. Phys. Chem. 100, 10892 (1996)

R.F.W. Bader, AIM 2000 Program, ver 2.0 (McMaster University, Hamilton, 2000)

R.F.W. Bader, P.J. MacDougall, C.D.H. Lau, J. Am. Chem. Soc. 106, 1594 (1984)

E. Espinosa, I. Alkorta, J. Elguero, E. Molins, J. Chem. Phys. 117, 5529 (2002)

J. Volkonen, I. Pitkanen, A. Pajanen, Acta Chem. Scand. A. 39, 711 (1985)

L.J. Bellany, The Infrared Spectra of Complex Molecules, 2nd edn. (Chapman and Hall, Boca Raton, 1980), pp. 241–254

K. Nakamoto, Infrared and Raman Spectra of Inorganic and Coordination Compounds, 4th edn. (Wiley, New York, 1986), pp. 101–188

D.H. William, I. Flemig, Spectroscopic Methods in Organic Chemistry, 4th edn. (MC Graw Hill, London, 1989), pp. 52–73