A smooth access to benzotriazoles via azide-benzyne cycloaddition

Tetrahedron

Volumn 64, Issue 49, 2008, Pages 11325-11327

  Chandrasekhar, S ^a   Seenaiah, M ^a   Rao, Ch Lohitha ^a   Reddy, Ch Raji ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Azide; Benzotriazole; Benzyne; Cesium fluoride; Cycloaddition

Indexed keywords

1 (1 (3,4 DIMETHOXYPHENYL)BUT 3 ENYL) 1H BENZO[D][1,2,3]TRIAZOLE; 1 (2 (4 ISOBUTYLPHENYL)PROPYL) 1H BENZO[D][1,2,3] TRIAZOLE; 1 (4 (BENZYLOXY) BUTYL) 1H BENZO[D][1,2,3]TRIAZOLE; 1 BENZYL 1H BENZO[D][1,2,3]TRIAZOLE; 4 (1H BENZO[D][1,2,3]TRIAZOL 1 YL) 5 (HYDROXYMETHYL0 TETRAHYDROFURAN 2 YL) 5 METHYL PYRIMIDINE 2,4(1H,3H) DIONE; 5 (2,2 DIMETHYL 1,3 DIOXOLAN 4 YL0 2,2 DIMETHYL TETRAHYDROFURO[2,3 D][1,3]DIOXOL 6 YL) 1H BENZO[D][1,2,3]TRIAZOLE; AZIDE; BENZOTRIAZOLE DERIVATIVE; METHYL 3 (1H BENZO[D][1,2,3]TRIAZOL 1 YL) 9 (4 METHOXYBENZYLOXY0 2 METHYLNONANOATE; TERT BUTYL 2 ((1H BENZO[D][1,2,3]TRIAZOL 1 YL)METHYLPYRROLIDINE 1 CARBOXYLATE; TERT BUTYL 4 ((1H BENZO[D][1,2,3]TRIAZOL 1 YL)METHYL) 2,2 DIMETHYLOXAZOLIDINE 3 CARBOXYLATE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 54549094637     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.08.115     Document Type: Article

References (28)

1. Katarzyna K., Najda A., Justyna Z., Chomicz L., Piekarczyk J., Myjak P., and Bretner M. Bioorg. Med. Chem. 12 (2004) 2617-2624
2. Al-Soud Y.A., Al-Masoudi N.A., and Ferwanah A.S. Bioorg. Med. Chem. 11 (2003) 1701-1708
3. Caliendo G., Greco G., Grieco P., Novelino E., Perissutti E., Santagada V., Barbarulo D., Esposito E., and De Blasi A. Eur. J. Med. Chem. 31 (1996) 207-213
4. Rewcastle G.W., Palmer B.D., Bridges A.J., Showalter H.D.H., Sun L., Nelson J., McMichael A., Kraker A.J., Fry D.W., and Denny W.A. J. Med. Chem. 39 (1996) 918-928
5. Katritzky A.R., Manju K., Singh S.K., and Meher N.K. Tetrahedron 61 (2005) 2555-2581
6. Katritzky A.R., and Rogovoy B.V. Chem.-Eur. J. 9 (2003) 4586-4593
7. Katritzky A.R., Lan X.F., Yang J.Z., and Denisko O.V. Chem. Rev. 98 (1998) 409-548
8. Katritzky A.R., Pleynet D.P.M., and Yang B. J. Org. Chem. 62 (1997) 4155-4158
9. Hagan D.J., Gimenez-Arnau E., Schwalbe C.H., and Stevens M.F. J. Chem. Soc., Perkin Trans. 1 (1997) 2739-2746
10. Miller R.B., and Stowell J.G. J. Org. Chem. 48 (1983) 886-888
11. Chan, M. S.; Hunter, W. E. U.S. Patent 4,299,965, 1981;
12. Muir J.C., Pattenden G., and Ye T. Tetrahedron Lett. 39 (1998) 2861-2864
13. Kitamura T., Fukatsu N., and Fujiwara Y. J. Org. Chem. 63 (1998) 8579-8581
14. Mitchell G., and Rees C.W. J. Chem. Soc., Perkin Trans. 1 (1987) 403-412
15. Reynolds G.A. J. Org. Chem. 29 (1964) 3733-3734
16. The starting materials used for the generation of benzyne were either explosive or commercially not available.
17. Himeshima Y., Sonoda T., and Kobayashi H. Chem. Lett. (1983) 1211-1214
18. Jin T., and Yamamoto Y. Angew. Chem., Int. Ed. 46 (2007) 3323-3325
19. Liu Z., Shi F., Martinez P.D.G., Raminelli C., and Larock R.C. J. Org. Chem. 73 (2008) 219-226
20. Huang X.-C., Liu Y.-L., Liang Y., Pi S.-F., Wang F., and Li J.-H. Org. Lett. 10 (2008) 1525-1528 and references cited therein
21. Chandrasekhar S., Basu D., and Rambabu Ch. Tetrahedron Lett. 47 (2006) 3059-3063
22. Chandrasekhar S., Rao Ch.L., Nagesh Ch., Reddy Ch.R., and Sridhar B. Tetrahedron Lett. 48 (2007) 5869-5872
23. Shi F., Waldo J.P., Chen Y., and Larock R.C. Org. Lett. 10 (2008) 2409-2412
24. Huisgen R. In: Padwa A. (Ed). 1,3-Dipolar Cycloaddition Chemistry (1984), Wiley, New York, NY
25. Tomoe C.M., Christensen C., and Meldal M. J. Org. Chem. 67 (2002) 3057-3064
26. Rostovtsev V.V., Green L.G., Fokin V.V., and Sharpless K.B. Angew. Chem., Int. Ed. 41 (2002) 2596-2599
27. Lutz J.F. Angew. Chem., Int. Ed. 47 (2008) 2-5
28. Gil M.V., Arevalo M.J., and Lopez O. Synthesis (2007) 1589-1620