Pure Appl. Chem., 2010, Vol. 82, No. 9, pp. 1761-1771
http://dx.doi.org/10.1351/PAC-CON-09-08-08
Published online 2010-06-19
Proximity-assisted cycloaddition reactions of ω‑azido cyanohydrin ethers: Synthesis of diversely functionalized bicyclic tetrazoles
References
- 1. J. A. . Ber. 18, 2907 (1885).
- 2a. R. J. . Bioorg. Med. Chem. 10, 3379 (2002). (http://dx.doi.org/10.1016/S0968-0896(02)00239-0)
- 2b. R. N. Butler. In Comprehensive Heterocyclic Chemistry, Vol. 4, A. R. Katritzky, C. W. Rees, E. F. Scriven (Eds.), Pergamon, Oxford (1996).
- 2c. S. J. . Org. Prep. Proced. Int. 26, 499 (1994) and refs. cited therein. (http://dx.doi.org/10.1080/00304949409458050)
- 3. For pertinent references, see.
- 3a. J. , D. G. Smith, J. B. Dunbar Jr., H. Iijima, G. R. Marshall. J. Am. Chem. Soc. 110, 5875 (1988). (http://dx.doi.org/10.1021/ja00225a045)
- 3b. J. , J. B. Dunbar, K. W. Marshall, M. V. Toth, G. R. Marshall. J. Org. Chem. 57, 202 (1992). (http://dx.doi.org/10.1021/jo00027a038)
- 4. For example, see.
- 4a. A. H. , D. D. McLeod, J. Li, K. Katipally, A. Littke, W. Doubleday, Z. Xu, C. W. McConlogue, C. J. Lai, M. Gleeson, M. Schwinde, R. L. Parsons Jr. J. Org. Chem. 74, 4068 (2009).
- 4b. D. J. , J. V. Duncia, P. E. Aldrich, A. T. Chiu, A. L. Johnson, M. E. Pierce, W. A. Price, J. B. Santella III, G. J. Wells, R. R. Wexler, P. C. Wong, S.-E. Yoo, P. B. M. W. M. Timmermans. J. Med. Chem. 34, 2525 (1991). (http://dx.doi.org/10.1021/jm00112a031)
- 4c. J. V. , F. M. Pierce, J. B. Santella III. J. Org. Chem. 56, 2395 (1991). (http://dx.doi.org/10.1021/jo00007a027)
- 4d. H. R. , J. Nussberger, B. Waeber. J. Hypertens. 15, 1221 (1993).
- 4e. H. R. , J. Nussberger, B. Waeber. J. Hypertens. 11, S53 (1993).
- 4f. W. R. . Vasc. Med. 2, 257 (1997).
- 4g. H. , A. S. Chawla, V. K. Kapoor, D. Paul, K. R. Malhotra. Prog. Med. Chem. 17, 151 (1980) and refs. cited therein. (http://dx.doi.org/10.1016/S0079-6468(08)70159-0)
- 5. For example, see.
- 5a. D. , R. Beleggia, F. Fringuelli, F. Pizzo, L. Vaccaro. J. Org. Chem. 69, 2896 (2004). (http://dx.doi.org/10.1021/jo0499468)
- 5b. J.-J. , J.-M. Fang. J. Org. Chem. 68, 1158 (2003). (http://dx.doi.org/10.1021/jo026407z)
- 5c. D. P. , S. Hadida, S.-Y. Kim. Tetrahedron 55, 8997 (1999). (http://dx.doi.org/10.1016/S0040-4020(99)00458-5)
- 5d. S. J. , B. G. Donner. J. Org. Chem. 58, 4139 (1993). (http://dx.doi.org/10.1021/jo00067a058)
- 6a. K. , M. Izumi. Bull. Chem. Soc. Jpn. 58, 2419 (1985). (http://dx.doi.org/10.1246/bcsj.58.2419)
- 6b. H. , K. K. Bhutani, R. K. Malhotra, D. Paul. J. Chem. Soc., Perkin Trans. 1 3166 (1979). (http://dx.doi.org/10.1039/p19790003166)
- 7. Z. P. , K. B. Sharpless. Angew. Chem., Int. Ed. 41, 2110 (2002). (http://dx.doi.org/10.1002/1521-3773(20020617)41:12<2110::AID-ANIE2110>3.0.CO;2-7)
- 8. For a review, see.
- 8a. H. C. , M. G. Finn, K. B. Sharpless. Angew. Chem., Int. Ed. 40, 2004 (2001); see also. (http://dx.doi.org/10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5)
- 8b. W. G. , L. G. Green, F. Gzynszpan, Z. Radić, P. R. Carlier, P. Taylor, M. G. Finn, K. B. Sharpless. Angew. Chem., Int. Ed. 41, 1053 (2002).
- 9a. W. von Kereszty. German Patent 611,962 (1936).
- 9b. W. R. . J. Org. Chem. 27, 2085 (1962). (http://dx.doi.org/10.1021/jo01053a043)
- 9c. P. A. S. , J. M. Clegg, J. H. Hall. J. Org. Chem. 23, 524 (1958). (http://dx.doi.org/10.1021/jo01098a006)
- 10a. B. , T. Brandstetter, C. Smith, L. Hackett, B. G. Winchester, G. K. Fleet. Tetrahedron Lett. 36, 7507 (1995). (http://dx.doi.org/10.1016/0040-4039(95)01518-3)
- 10b. B. , R. J. Nash, A. A. Watson, C. Smith, G. W. J. Fleet. Tetrahedron 55, 4501 (1999). (http://dx.doi.org/10.1016/S0040-4020(99)00138-6)
- 11. R. I. , V. G. Puranik, S. Hotha. Org. Biomol. Chem. 6, 779 (2008). (http://dx.doi.org/10.1039/b716996e)
- 12. For example, see.
- 12a. Z. P. , K. B. Sharpless. Org. Lett. 3, 4091 (2001). (http://dx.doi.org/10.1021/ol010220x)
- 12b. T. C. , K. K. Smalley, M. Teguiche, B. Purwood. Synthesis 773 (1997). (http://dx.doi.org/10.1055/s-1997-1416)
- 13. For indirect methods toward bicyclic tetrazoles, see: F. , L.-G. Wistrand, T. Frejd. Tetrahedron 59, 6759 (2003). (http://dx.doi.org/10.1016/S0040-4020(03)00818-4)
- 14a. S. , S. Marcotte, R. Machaalani, G. Huang. Org. Lett. 5, 4277 (2003). (http://dx.doi.org/10.1021/ol030095k)
- 14b. S. , S. Marcotte, R. Machaalani, G. Huang, J. Pierron, O. Loiseleur. Tetrahedron 62, 5201 (2006). (http://dx.doi.org/10.1016/j.tet.2005.12.066)
- 15a. S. , D. Simard, B. Deschênes-Simard, C. Chenel, E. Haak. Org. Lett. 10, 1381 (2008). (http://dx.doi.org/10.1021/ol703071c)
- 15b. S. , B. Deschênes-Simard, D. Simard. Tetrahedron 65, 6656 (2009). (http://dx.doi.org/10.1016/j.tet.2009.06.033)
- 16. For relevant literature on acetals and Lewis acid-mediated reactions, see.
- 16a. T. , R. S. Smith. J. Am. Chem. Soc. 116, 7915 (1994). (http://dx.doi.org/10.1021/ja00096a066)
- 16b. S. E. , N. G. Almstead. J. Am. Chem. Soc. 113, 8089 (1991). (http://dx.doi.org/10.1021/ja00021a040)
- 16c. I. , K. Ishihara, L. A. Flippin, K. Nozaki, H. Yamamoto, P. A. Bartlett, C. H. Heathcock. J. Org. Chem. 55, 6107 (1990). (http://dx.doi.org/10.1021/jo00312a015)
- 16d. R. C. . Tetrahedron Lett. 31, 2101 (1990). (http://dx.doi.org/10.1016/0040-4039(90)80082-W)
- 17. For pertinent literature on cyanohydrins, see.
- 17a. J.-M. , I. P. Holmes. Angew. Chem., Int. Ed. 43, 2752 (2004). (http://dx.doi.org/10.1002/anie.200300604)
- 17b. R. H. . Chem. Rev. 99, 3649 (1999). (http://dx.doi.org/10.1021/cr9902906)
- 18. For example, see.
- 18a. Y. , J. J. Rohde, E. J. Corey. J. Am. Chem. Soc. 118, 5502 (1996). (http://dx.doi.org/10.1021/ja960766s)
- 18b. W. , E. F. Mooney, W. G. Peterson. J. Inorg. Nucl. Chem. 29, 943 (1967). (http://dx.doi.org/10.1016/0022-1902(67)80076-9)
- 19. For a study of Lewis acids in 1,3-dipolar cycloaddition reactions, see: F. , Z. P. Demko, L. Noodleman, K. B. Sharpless. J. Am. Chem. Soc. 125, 9983 (2003). (http://dx.doi.org/10.1021/ja030204q)
- 20. P. C. , J. F. Gal. J. Phys. Chem. 89, 1296 (1985). (http://dx.doi.org/10.1021/j100253a048)
- 21a. J. , J. G. Badiang. J. Org. Chem. 61, 2484 (1996).
- 21b. K. , V. Gracias, K. Furness, B.-T. Smith, C. E. Reddy, J. Aubé. J. Am. Chem. Soc. 125, 7914 (2003). (http://dx.doi.org/10.1021/ja0348896)
- 22. J. E. . J. Chem. Soc., Chem. Commun. 734 (1976). (http://dx.doi.org/10.1039/c39760000734)
