Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2012; 23(19): 2795-2798
DOI: 10.1055/s-0032-1317513
DOI: 10.1055/s-0032-1317513
letter
Ultrasound-Promoted Regioselective Synthesis of 1-Aryl-5-amino-1H-tetrazoles
Further Information
Publication History
Received: 24 August 2012
Accepted after revision: 05 October 2012
Publication Date:
09 November 2012 (online)
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.
-
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