Synlett, Table of Contents Synlett 2012; 23(19): 2795-2798DOI: 10.1055/s-0032-1317513 letter © Georg Thieme Verlag Stuttgart · New York Ultrasound-Promoted Regioselective Synthesis of 1-Aryl-5-amino-1H-tetrazoles Davood Habibi* a Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, Hamedan 6517838683, Iran , Mahmoud Nasrollahzadeh b Department of Chemistry, Faculty of Science, University of Qom, PO Box 37185-359, Iran , Hesam Sahebekhtiari a Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, Hamedan 6517838683, Iran , S. Mohammad Sajadi c Department of Petroleum Geoscience, Faculty of Science, Soran University, PO Box 624, Soran, Kurdistan Regional Government, Iraq › Author Affiliations Recommend Article Abstract Buy Article All articles of this category Abstract A new method for the regioselective synthesis of 1-aryl-5-amino-1H-tetrazoles has been developed by the reaction of arylcyanamides with sodium azide using ZnCl2 under ultrasound irradiation in excellent yields. Key words Key words1-aryl-5-amino-1H-tetrazole - cyanamide - sodium azide - ZnCl2 - sonochemical switching Full Text References References 1 Herr RJ. Bioorg. Med. Chem. 2002; 10: 3379 2 White AD, Creswell MW, Chucholowski AW, Blankley CJ, Wilson MW, Bousley RF, Essenburg AD, Hamelehle KL, Krause BR, Stanfield RL, Dominick MA, Neub M. J. Med. Chem. 1996; 39: 4382 3a Sung RL. US 4445907, 1984 ; Chem. Abstr. 1984, 101, 40827k. 3b Zhilin AY, Ilyushin MA, Tselinskii IV, Kozlov AS, Lisker IS. Russ. J. Appl. Chem. 2003; 76: 572 4 Friedrich M, Galvez-Ruiz JC, Klapötke TM, Mayer P, Weber B, Weigand J. Inorg. Chem. 2005; 44: 8044 5 Modarresi-Alam AR, Khamooshi F, Rostamizadeh M, Keykha H, Nasrollahzadeh M, Bijanzadeh HR, Kleinpeter E. J. Mol. Struct. 2007; 841: 67 6a Connor DT, Unangst PC, Weikert RJ. EP 279466, 1988 ; Chem. Abstr. 1988, 109, 231035. 6b Peet NP, Baugh LE, Sundler S, Lewis JE, Matthews EH, Olberding EL, Shah DN. J. Med. Chem. 1986; 29: 2403 7 Girijavallabhan VM, Pinto PA, Ganguly AK, Versace RW. EP 274867, 1988 ; Chem. Abstr. 1989, 110, 23890. 8 Taveras AG, Mallams AK, Afonso A. WO 9811093, 1998 ; Chem. Abstr. 1998, 128, 230253 9 Mitch CH, Quimby SJ. WO 9851312, 1998 ; Chem. Abstr. 1998, 130, 13997. 10a Henry RA, Finnegan WG. J. Am. Chem. Soc. 1954; 76: 926 10b Finnegan WG, Henry RA. J. Org. Chem. 1959; 24: 1565 10c Barmin MI, Gromova SA, Mel’nikov VV. Russ. J. Appl. Chem. 2001; 74: 1156 11 Batey RA, Powell DA. Org. Lett. 2000; 2: 3237 12 Joo YH, Shreeve JM. Org. Lett. 2008; 10: 4665 13 Garbrecht WL, Herbst RM. J. Org. Chem. 1953; 18: 1014 14 Congreve MS. Synlett 1996; 359 15 Vorobiey AN, Gaponik PN, Petrov PT, Ivashkevich OA. Synthesis 2006; 1307 16a Nasrollahzadeh M, Habibi D, Shahkarami Z, Bayat Y. Tetrahedron 2009; 65: 10715 16b Modarresi-Alam AR, Nasrollahzadeh M. Turk. J. Chem. 2009; 33: 267 16c Kamali TA, Habibi D, Nasrollahzadeh M. Synlett 2009; 2601 16d Kamali TA, Bakherad M, Nasrollahzadeh M, Farhangi S, Habibi D. Tetrahedron Lett. 2009; 50: 5459 16e Nasrollahzadeh M, Bayat Y, Habibi D, Moshaee S. Tetrahedron Lett. 2009; 50: 4435 16f Habibi D, Nasrollahzadeh M, Faraji AR, Bayat Y. Tetrahedron 2010; 66: 3866 16g Habibi D, Nasrollahzadeh M. Synth. Commun. 2010; 40: 3159 16h Mohammadi B, Hosseini Jamkarani SM, Kamali TA, Nasrollahzadeh M, Mohajeri A. Turk. J. Chem. 2010; 34: 613 16i Habibi D, Nasrollahzadeh M, Kamali TA. Green Chem. 2011; 13: 3499 16j Habibi D, Nasrollahzadeh M, Bayat Y. Synth. Commun. 2011; 41: 2135 16k Habibi D, Nasrollahzadeh M. Monatsh. Chem. 2012; 143: 925 16l Habibi D, Nasrollahzadeh M. Synth. Commun. 2012; 42: 2023 17a Finnegan WG, Henry RA, Lieber E. J. Org. Chem. 1953; 18: 779 17b Henry RA, Finnegan WG, Lieber E. J. Am. Chem. Soc. 1954; 76: 88
