TBAF-Catalyzed Synthesis of 5-Substituted 1H-Tetrazoles under Solventless Conditions

Journal of Organic Chemistry

Volumn 69, Issue 8, 2004, Pages 2896-2898

  Amantini, David ^a   Beleggia, Romina ^a   Fringuelli, Francesco ^a   Pizzo, Ferdinando ^a   Vaccaro, Luigi ^a  

^a UNIVERSITY OF PERUGIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; NITRILE RESINS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

CYCLOADDITION;

ORGANIC COMPOUNDS;

AZIDE; NITRILE; SOLVENT; TETRABUTYLAMMONIUM; TETRABUTYLAMMONIUM FLUORIDE; TETRAZOLE DERIVATIVE; TRIMETHYLSILYL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CYCLOADDITION; QUANTUM YIELD; REACTION ANALYSIS; SYNTHESIS;

EID: 1842688821     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0499468     Document Type: Article

References (31)

1. Butler, R. N. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: Oxford, U.K., 1996; Vol. 4.
2. Singh, H.; Chawla, A. S.; Kapoor, V. K.; Paul, D.; Malhotra, R. K. Prog. Med. Chem. 1980, 17, 151-183.
3. Huisgen, R.; Sauer, J.; Sturm, H. J.; Markgraf, J. H. Chem. Ber. 1960, 93, 2106-2124.
4. (b) Moderhack, D. J. Prakt. Chem./Chem.-Ztg. 1988, 340, 687-709.
5. Ostrovskii, V. A.; Pevzner, M. S.; Kofmna, T. P.; Shcherbinin, M. B.; Tselinskii, I. V. Targets Heterocycl. Syst. 1999, 3, 467-526.
6. (b) Koldobskii, G. I.; Ostrovskii, V. A. Usp. Khim. 1994, 63, 847-865.
7. Duncia, J. V.; Pierce, M. E.; Santella, J. B., III. J. Org. Chem. 1991, 56, 2395-2400.
8. (b) Huff, B. E.; Staszak, M. A. Tetrahedron Lett. 1993, 34, 8011-8014.
9. (c) Wittenberger, S. J.; Donner, B. G. J. Org. Chem. 1993, 58, 4139-4141.
10. (d) Koguro, K.; Oga, T.; Mitsui, S.; Orita, R. Synthesis 1998, 910-914.
11. (e) Curran, D. P.; Hadida, S.; Kim, S.-Y. Tetrahedron 1999, 55, 8997-9006.
12. Demko, Z. P.; Sharpless, K. B. J. Org. Chem. 2001, 66, 7945-7950.
13. (b) Demko, Z. P.; Sharpless, K. B. Org. Lett. 2002, 4, 2525-2527.
14. (c) Himo, F.; Demko, Z. P.; Noodleman, L.; Sharpless, K. B. J. Am. Chem. Soc. 2002, 124, 12210-12216.
15. (d) Himo, F.; Demko, Z. P.; Noodleman, L.; Sharpless, K. B. J. Am. Chem. Soc. 2003, 125, 9983-9987.
16. For more recent papers, see: (a) Fringuelli, F.; Pizzo, F.; Vaccaro L. Synthesis 2000, 646-650.
17. (b) Amantini, D.; Fringuelli, F.; Piermatti, O.; Pizzo, F.; Vaccaro, L. Green Chem. 2001, 3, 229-232.
18. (c) Fringuelli, F.; Matteucci, M.; Piermatti, O.; Pizzo, F.; Burla M. C. J. Org. Chem. 2001, 66, 4661-4666.
19. (d) Fioroni, G.; Fringuelli, F.; Pizzo, F.; Vaccaro, L. Green Chem. 2003, 5, 425-428.
20. (e) Fringuelli, F.; Pizzo, F.; Rucci, M. Vaccaro, L. J. Org. Chem. 2003, 68, 7041-7045.
21. (f) Fringuelli, F.; Pizzo, F.; Tortoioli, S.; Vaccaro, L. J. Org. Chem. 2003, 68, 8248-8251.
22. (g) Fringuelli, F.; Piermatti, O.; Pizzo, F. Synthesis 2003, 2331-2334.
23. (h) Amantini, D.; Fringuelli, F.; Piermatti, O.; Pizzo, F.; Vaccaro, L. J. Org. Chem. 2003, 68, 9263-9268.
24. Amantini, D.; Fringuelli, F.; Pizzo, F.; Vaccaro, L. J. Org. Chem. 2001, 66, 6734-6737.
25. (b) Amantini, D.; Fringuelli, F.; Pizzo, F. J. Org. Chem. 2002, 67, 7238-7243.
26. (c) Fringuelli, F.; Pizzo, F.; Tortoioli, S.; Vaccaro, L. Tetrahedron Lett 2003, 44, 6785-6787.
27. Corriu, R. J. P.; Perz, R.; Reye, C. Tetrahedron 1983, 39, 999-1009.
28. When alkyltin or alkylsilicon azide reagents are used, a subsequent deprotection step is normally required.
29. 3/ 15-crown-5 and metal halide catalyzed conditions: Nishiyama, K.; Yamaguchi, T. Synthesis 1988, 106-108.
30. Le Bourdonnec, B.; Meulon, E.; Yous, S.; Goossens, J.-F.; Houssin, R.; Hénichart, J.-P. J. Med. Chem. 2000, 43, 2685-2697 and references therein.
31. 4) and concentrated under reduced pressure to furnish pure 5-phenyl-1-H-tetrazole (2a) as a white solid in 86% yield (0.251 g).