A convenient synthesis of tetrazolo[1,5-a]-α-cycloalkanones

Tetrahedron Letters

Volumn 48, Issue 4, 2007, Pages 555-558

  Shi, Yan ^a   Robl, Jeffrey A ^a   Kennedy, Lawrence J ^a   Malley, Mary F ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5,6,7,8 TETRAHYDROTETRAZOLO[1,5 A]AZEPIN 9 ONE; ALKENE; AZEPINE DERIVATIVE; CARBENE; CARBONYL DERIVATIVE; CYCLOALKANONE; TETRAZOLE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; OZONOLYSIS; SYNTHESIS;

EID: 33845626111     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.11.125     Document Type: Article

References (40)

1. Only one tetrazole natural product has been reported, see:. Hossain M.B., and Helm D.V.D. Acta Crystallogr., Sect. C (1985) 1199
2. For reviews on the chemistry of tetrazoles, see:. Bulter R.N. In: Katritzky A.R., and Rees C.W. (Eds). Comprehensive Heterocyclic Chemistry Vol. 5 (1984), Pergamon Press, Oxford 791
3. Meier H.R., and Heimgartner H. In: Schamann E. (Ed). Methoden der Organischen Chemie (1994), Thieme, Stuttgart 664
4. Marshall G.R., Humblet C., Van Opdenbosch N., and Zabrocki J. In: Rich D.H., and Gross E. (Eds). Peptides: Synthesis-Structure-Function. Proceedings of the Seventh American Peptide Symposium (1981), Pierce Chemical Company, Rockford, IL 669
5. Zabrocki J., Smith D.G., Dunbar Jr. J.B., Iijima H., and Marshall G.R. J. Am. Chem. Soc. 110 (1988) 5875
6. Yu K.-L., and Johnson R.L. J. Org. Chem. 52 (1987) 2051
7. Bavetsias V., Bisset G.M.F., Kimbell R., Boyle T., and Jackman A.L. Tetrahedron 53 (1997) 13383
8. Batey R.A., and Powell D.A. Org. Lett. 2 (2000) 3237
9. A cholestan-6-one fused tetrazole ketone has been reported, see:. Ahmad M.S., and Alam Z. Indian J. Chem. 27B (1988) 1001
10. A phthaloyl-1,5-1H-tetrazole has been reported, see:. Moore H.W., and Pearce D.S. Tetrahedron Lett. 12 (1971) 1621
11. Satoh Y., and Moliterni J. Synlett (1998) 528
12. Kumar S., Pearson A.L., and Pratt R.F. Bioorg. Med. Chem. 9 (2001) 2035
13. Edwards P.D., Wolanin D.J., Andisik D.W., and Davis M.W. J. Med. Chem. 38 (1995) 76
14. Satoh Y., and Marcopulos N. Tetrahedron Lett. 36 (1995) 1759
15. Abell A.D., and Foulds G.J. J. Chem. Soc., Perkin Trans. 1 (1997) 2475
16. May B.C.H., and Abell A.D. Tetrahedron Lett. 42 (2001) 5641
17. Johansson A., Poliakov A., Åkerblom E., Wiklund K., Lindeberg G., Winiwarter S., Danielson U.H., Samuelsson B., and Hallberg A. Bioorg. Med. Chem. Lett. 11 (2003) 2551
18. Harvill E.K., Herbst R.M., and Schreiner E.G. J. Org. Chem. 17 (1952) 1597
19. Jacobson C.R., and Amstutz E.D. J. Org. Chem. 19 (1954) 1652
20. Fisher B.E., Tomson A.J., and Horwitz J.P. J. Org. Chem. 24 (1959) 1650
21. Moderhack D., and Beißner A. Z. Naturforsch. 51b (1996) 1815
22. Takach N.E., Holt E.M., Alcock N.W., Henry R.A., and Nelson J.H. J. Am. Chem. Soc. 102 (1980) 2968
23. Andrus A., Heck J.V., Christensen B.G., and Partridge B. J. Am. Chem. Soc. 106 (1984) 1808
24. Bookser B.C., Kasibhatla S.R., Appleman J.R., and Erion M.D. J. Med. Chem. 43 (2000) 1495
25. Isida T., Akiyama T., Nabika K., Sisaido K., and Kozima S. Bull. Chem. Soc. Jpn. 46 (1973) 2176
26. Ermert P., and Vasella A. Helv. Chim. Acta 74 (1991) 2043
27. Davis B., Brandstetter T.W., Smith C., Hackett L., Winchester B.G., and Fleet G.W.J. Tetrahedron Lett. 36 (1995) 7507
28. Moreaux V., Warren H., and Williams J.M. Tetrahedron Lett. 38 (1997) 4566
29. Vonhoff S., and Vasella A. Synth. Commun. 29 (1999) 551
30. EI-AhI A.S., Elmorsy S.S., Soliman H., and Amer F.A. Tetrahedron Lett. 36 (1995) 7337
31. Eshghi H., and Hassankhani A. Synth. Commun. 35 (2005) 115
32. Suzuki H., Hwang Y.S., Nakaya C., and Matano Y. Synthesis (1993) 1218
33. Banik B.K., Venkatraman M.S., Mukhopadhyay C., and Becker F.F. Tetrahedron Lett. 39 (1998) 7247
34. Murahashi S.-I., Komiya N., Oda Y., Kuwabara T., and Naota T. J. Org. Chem. 65 (2000) 9186
35. Harvey R.G., Abu-shqara E., and Yang C.-X. J. Org. Chem. 57 (1992) 6313
36. The addition of α-lithio-1-methyl-5-ethyltetrazole to 4,4′-difluorobenzophenone and subsequent dehydration to generate an α-olefinic tetrazole has been previously reported, see:. Sit S.Y., Parker R.A., Motoc I., Han W., Balasubramanian N., Catt J.D., Brown P.J., Harte W.E., Thompson M.D., and Wright J.J. J. Med. Chem. 33 (1990) 2982
37. 4O: C, 47.36; H, 5.30; N, 36.82. Found: C, 47.30; H, 5.25; N, 36.81.
38. It has been demonstrated that 5-substituted-1-alkyltetrazoles can be lithiated at the alkyl carbon attached to the nitrogen and react with electrophiles, see:. Moody C.J., Rees C.W., and Young R.G. J. Chem. Soc., Perkin Trans. 1 (1991) 323
39. Thomas E.W., and Cudahy M.M. J. Org. Chem. 58 (1993) 1623
40. w = 0.14). CCDC 627731 and CCDC 627732 contain the supplementary crystallographic data (excluding structure factors) for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.