AlCl3 as an effective lewis acid for the synthesis of arylaminotetrazoles

Synthetic Communications

Volumn 41, Issue 14, 2011, Pages 2135-2145

  Habibi, Davood ^a   Nasrollahzadeh, Mahmoud ^a   Bayat, Yadollah ^b  

^a BU ALI SINA UNIVERSITY   (Iran)

^b MALEK ASHTAR UNIVERSITY OF TECHNOLOGY   (Iran)

Author keywords

1 aryl 5 amino 1H tetrazole; 5 arylamino 1H tetrazole; AlCl3; Arylcyanamide; Lewis acid

Indexed keywords

ALUMINUM CHLORIDE; ARYLAMINOTETRAZOLE; LEWIS ACID; TETRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; ELECTRON; ISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 79957642146     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2010.497728     Document Type: Article

References (49)

1. Bulter, R. N. Comprehensive Heterocyclic Chemistry II; A. R. Katritzky, C. W. Ress, and E. F. V. Scriven (Eds.); Pergamon: New York, 1996; vol. 4.
2. Herr, R. 5-Substituted-1H-tetrazoles as carboxylic acid isosteres: Medicinal chemistry and synthetic methods. J. Bioorg. Med. Chem. 2002, 10, 3379-3393.
3. Holland, G. F.; Pereira, J. N. Heterocyclic tetrazoles, a new class of lipolysis inhibitors. J. Med. Chem. 1967, 10, 149-154.
4. Figdor, S. K.; Schach von Wittenau, M. Metabolism of 5-(3-pyridyl) tetrazole. J. Med. Chem. 1967, 10, 1158-1159.
5. Esplin, D. W.; Woodbury, D. M. The fate and excretion of C14-labeled pentylenetetrazole in the rat, with comments on analytical methods for pentylenetetrazole. J. Pharmacol. Exp. Ther. 1956, 118, 129-138.
6. Flippin, L. A. Directed metalation and new synthetic transformations of 5-aryl-tetrazoles. Tetrahedron Lett. 1991, 32, 6857-6860.
7. Rhonnstad, P.; Wensbo, D. On the relative strength of the 1H-tetrazol-5-yl and the 2-(triphenylmethyl)-2H-tetrazol-5-yl-group in directed ortho-lithiation. Tetrahedron Lett. 2002, 43, 3137-3139. (Pubitemid 34310392)
8. Ek, F.; Wistrand, L.-G.; Frejd, T. Synthesis of fused tetrazole- and imidazole derivatives via iodocyclization. Tetrahedron 2003, 59, 6759-6769. (Pubitemid 36976660)
9. Sandmann, G.; Schneider, C.; Boger, P. A new non-radioactive assay of phytoene desaturase to evaluate bleaching herbicides. Z. Naturforsch. C. Biosci. 1996, 51, 534-538. (Pubitemid 26350957)
10. Jursic, B. S.; LeBlanc, B. W. Preparation of tetrazoles from organic nitriles and sodium azide in micellar media. J. Heterocycl. Chem. 1998, 35, 405-408. (Pubitemid 128494367)
11. Zhao-Xu, C.; Heming, X. Impact sensitivity and activation energy of pyrolysis for tetrazole compounds. Int. J. Quantum Chem. 2000, 79, 350-357.
12. Modarresi-Alam, A. R.; Khamooshi, F.; Rostamizadeh, M.; Keykha, H.; Nasrollahzadeh, M.; Bijanzadeh, H. R.; Kleinpeter, E. Dynamic 1H NMR spectroscopic study of the restricted S-N rotation in aryl-N-(arylsulfonyl)-N- (triphenylphosphoranylidene) imidocarbamates. J. Mol. Struc. 2007, 841, 61-66. (Pubitemid 47331485)
13. Finnegan, W. G.; Henry, R. A.; Lieber, E. Preparation and isomerization of 5-alkylaminotetrazoles. J. Org. Chem. 1953, 18, 779-791.
14. Jensen, K. A.; Holm, A.; Rachlin, S. The reaction between 5-dimethylamino-tetrazole and sulfonyl chlorides. Acta Chem. Scand. 1966, 20, 2795-2806.
15. Percival, D. F.; Herbst, R. M. Alkylated 5-aminotetrazoles, their preparation and properties. J. Org. Chem. 1957, 22, 925-933.
16. Moderhack, D.; Goos, K.-H.; Preu, L. Dimroth-umlagerung von iminen des 1,5-diaminotetrazols. Chem. Ber. 1990, 123, 1575-1578.
17. Herbst, R. M.; Roberts, C. W.; Harvill, E. The synthesis of 5-aminotetrazole derivatives. J. Org. Chem. 1951, 16, 139-149.
18. Klich, M.; Teutsch, G. Synthese de n-(tetrazol-5-yl)azetidin-2-ones. Tetrahedron 1986, 42, 2677-2684.
19. Barlin, G. B. The relative electron-releasing power of a singly bound, and the electron-attracting power of a doubly bound nitrogen atom when present in the same five-membered ring. J. Chem. Soc. B 1967, 641-647.
20. Miller,A. E.; Feenay,D. J.;Ma, Y.; Zarcone, L.; Aziz,M. A.; Magnuson, E. The synthesis of aminoiminoethanenitriles, 5-aminotetrazoles,N-cyanoguanidines, andN-hydroxyguanidines from aminoiminomethanesulfonic acids. Synth. Commun. 1990, 20, 217-226.
21. Batey, R. A.; Powell, D. A. A general synthetic method for the formation of substituted 5-aminotetrazoles from thioureas: A strategy for diversity amplification. Org. Lett. 2000, 2, 3237-3240.
22. Yu, Y.; Ostresh, J. M.; Houghten, R. A. Solid-phase synthesis of 5-amino-tetrazoles. Tetrahedron Lett. 2004, 45, 7787-7789.
23. Henry, R. A.; Finnegan, W. G.; Lieber, E. Thermal isomerization of substituted 5-aminotetrazoles. J. Am. Chem. Soc. 1954, 76, 88-93.
24. Garbrecht, W. L.; Herbst, R. M. The synthesis of certain 5-aminotetrazole derivatives, II. The action of hydrazoic acid on monoalkylcyanamides. J. Org. Chem. 1953, 18, 1014-1021.
25. Congreve, M. S. Synthesis of 5-N-substituted tetrazole derivatives of the potent NK1 receptor antagonist GR20304. Synlett. 1996, 359-360. (Pubitemid 126439680)
26. Vorobiev, A. N.; Gaponik, P. N.; Petrov, P. T. The convenient synthesis of 5-amino-1- aryltetrazoles. Vestsi Nats. Akad. Navuk Belarusi, Ser. Khim. Navuk. 2003, 2, 50-53;
27. Chem. Abstr. 2004, 140, 16784g.
28. 2 as a reusable heterogeneous catalyst for the synthesis of 5-substituted 1H-tetrazoles via [2+3] cycloaddition of nitriles and sodium azide. Tetrahedron Lett. 2009, 50, 4435-4438.
29. Kamali, T. A.; Bakherad, M.; Nasrollahzadeh, M.; Farhangi, S.; Habibi, D. Synthesis of 6-substituted imidazo[2,1-b]thiazoles via Pd=Cu-mediated Sonogashira coupling in water. Tetrahedron Lett. 2009, 50, 5459-5462.
30. Kamali, T. A.; Habibi, D.; Nasrollahzadeh, M. Synthesis of 6-substituted imidazo[2,1-b] [1,3]thiazoles and 2-substituted imidazo[2,1-b][1,3]benzo- thiazoles via Pd=Cu-mediated Sonogashira coupling. Synlett. 2009, 2601-2604.
31. 4)3-mediated for the preparation of primary carbamates under solvent-free conditions. Scientia Iranica 2008, 15, 452-455.
32. Modarresi-Alam, A. R.; Nasrollahzadeh, M.; Khamooshi, F. Solvent-free preparation of primary carbamates using silica sulfuric acid as an efficient reagent. Arkivoc 2007, 16, 234-245.
33. 2): An efficient reagent for the preparation of primary carbamates under solvent-free conditions. Tetrahedron 2007, 63, 8723-8726. (Pubitemid 47087881)
34. Crutchley, R. J.; Nakicki, M. L. Pentaammineruthenium(III) complexes of neutral and anionic (2,3-dichlorophenyl)cyanamide: A spectroscopic analysis of ligand to metal charge-transfer spectra. Inorg. Chem. 1989, 28, 1955-1958.
35. Castro, J. L.; Ball, R. G.; Broughton, H. B.; Russell, M. G. N.; Rathbone, D.; Watt, A. P.; Baker, R.; Chapman, K. L.; Fletcher, A. E.; Patel, S.; Smith, A. J.; Marshall, G. R.; Ryecroft, W.; Matasa, V. G. Controlled modification of acidity in cholecystokinin B receptor antagonists: N-(1,4-Benzodiazepin-3-yl)-N0-[3-(tetrazol-5-ylamino)phenyl]ureas. J. Med. Chem. 1996, 39, 842-849.
36. Koguro, K.; Oga, T.; Mitsui, S.; Orita, R. Novel synthesis of 5-substituted tetrazoles from nitriles. Synthesis 1998, 910-914. (Pubitemid 28282819)
37. Butler, R. N. Recent advances in tetrazole chemistry. Adv. Het. Chem. 1977, 21, 323-435.
38. Wittenberger, S. J. Recent developments in tetrazole chemistry: A review. Org. Prep. Proc. Int. 1994, 26, 499-532.
39. Benson, F. R. The chemistry of the tetrazoles. Chem. Rev. 1947, 47, 1-61.
40. Kadaba, P. K. Role of Protic and dipolar aprotic solvents in cycloaddition reactions involving anionic 1,3-dipoles: Action of inorganic azides on imidoyl chlorides. J. Org. Chem. 1976, 41, 1073-1075.
41. Henry, R. A.; Finnegan, W. G.; Lieber, E. Kinetics of the isomerization of substituted 5-aminotetrazoles. J. Am. Chem. Soc. 1955, 77, 2264-2270.
42. Garbrecht, W. L.; Herbst, R. M. The synthesis of certain 5-aminotetrazole derivatives, I: The action of hydrazoic acid on some dialkylcyanamides. J. Org. Chem. 1953, 18, 1003-1013.
43. Garbrecht, W. L.; Herbst, R. M. The synthesis of certain 5-aminotetrazole derivatives, III: The synthesis of certain 5-monoalkylaminotetrazoles. J. Org. Chem. 1953, 18, 1022-1029.
44. Butler, R. N.; Garvin, N. L. A study of annular tautomerism, interannular conjugation, and methylation reactions of ortho-substituted-5-aryltetrazoles using carbon-13 and hydrogen-1 NMR spectroscopy. J. Chem. Soc., Perkin Trans. 1 1981, 390-393.
45. Butler, R. N. A study of the proton nuclear magnetic resonance spectra of aryl and monoand disubstituted N-methylazoles. Can. J. Chem. 1972, 51, 2315-2322.
46. Batterhan, T. J. NMR Spectra of Simple Heterocycles; Wiley: New York, 1973.
47. Goljer, I.; Svetlik, J.; Hrusovsky, I. 13C-NMR of substituted tetrazoles. Monatsh. Chem. 1983, 114, 65-70.
48. Hansch, C.; Leo, A.; Taft, R. W. A survey of hammett substituent constants and resonance and field parameters. Chem. Rev. 1991, 91, 165-195.
49. Günnter, H. NMR Spectroscopy, 2nd ed., Wiley: New York, 1995.