Syntheses of imidazoles and pyrroles: Betmic and tosmic as complementary reagents

Heterocycles

Volumn 44, Issue 1, 1997, Pages 67-70

  Katritzky, Alan R ^a   Cheng, Dai ^a   Musgrave, Richard P ^a  

^a University of Florida ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002555782     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-95-s5     Document Type: Article

References (26)

1. A. M. van Leusen, Lect. Heterocycl. Chem., 1980, 5, S111.
2. S. Marcaccini and T. Torroba, Org. Prep. Proced. Int., 1993, 25, 143.
3. D. Hoppe, Angew. Chem., Int. Ed. Engl., 1974, 13, 789.
4. U. Schöllkopf, Angew. Chem., Int. Ed. Engl., 1977, 16, 339.
5. A. M. van Leusen, B. E. Hoogenboom and H. Siderius, Tetrahedron Lett., 1972, 13, 2369.
6. O. Possel and A. M. van Leusen, Heterocycles, 1977, 7, 77.
7. A. M. van Leusen, J. Wildeman and O. H. Oldenziel, J. Org. Chem., 1977, 42, 1153.
8. A. M. van Leusen, H. Siderius, B. E. Hoogenboom and D. van Leusen, Tetrahedron Lett., 1972, 13, 5337.
9. D. van Leusen, E. Flentge and A. M. van Leusen, Tetrahedron, 1991, 47, 4639.
10. D. H. R. Barton, J. Kervagoret and S. Z. Zard, Tetrahedron, 1990, 46, 7587.
11. D. van Leusen, E. van Echten and A. M. van Leusen, J. Org. Chem., 1992, 57, 2245.
12. S. P. J. M. van Nispen, J. H. Bregman, D. G. van Engen, A. M. van Leusen, H. Saikachi, T. Kitagawa, and H. Sasaki, Recl. Trav. Chim. Pays-Bas, 1982, 101, 28.
13. O. Possel and A. M. van Leusen, Tetrahedron Lett., 1977, 18, 4229.
14. O. H. Oldenziel, A. M. van Leusen, Tetrahedron Lett., 1974, 15, 167.
15. D. van Leusen and A. M. van Leusen, Tetrahedron Lett., 1984, 25, 2581.
16. D. van Leusen, E. van Echten and A. M. van Leusen, Recl. Trav. Chim. Pays-Bas, 1992, 111, 469.
17. J. Moskal, R. van Stralen, D. Postma and A. M. van Leusen, Tetrahedron Lett., 1986, 27, 2173.
18. J. Moskal and A. M. van Leusen, J. Org. Chem., 1986, 51, 4131.
19. K. Aoyagi, H. Toi, Y. Aoyama and H. Ogoshi, Chem. Lett., 1988, 1891.
20. (a) A. R. Katritzky, Y. X. Chen, K. Yannakopoulou and P. Lue, Tetrahedron Lett., 1989, 30, 6657.
21. (b) A. R. Katritzky, M. Sutharchanadevi and L. Urogdi, J. Chem. Soc., Perkin Trans. 1, 1990, 1847.
22. 4) and evaporated to dryness. Column chromatography (silica, ethyl acetate/hexane 1:3) gave, as oils, isolated yields of 53% for 1-(benzotriazol-1-yl)ethyl isocyanide (3) and 50% for 1-(benzotriazol-1-yl)-2-phenylethyl isocyanide (4). Microanalytical data was within ±0.4% of the expected values for C and H.
23. 4), evaporated to dryness and the residue subjected to column chromatography (silica, ethyl acetate/hexane 1:1).
24. W. L. Collibee and J. P. Anselme, Bull. Soc. Chim. Belg., 1986, 95, 655.
25. 4) were evaporated to dryness and the residue subjected to column chromatography (silica, ethyl acetate/hexane 1:1). Method B: This procedure is similar to the above method except that a solution of potassium tert-butoxide (1.12g, 10 mmol) in THF (15 ml) was added to a solution of BetMIC (or derivative) in THF (15 ml) at -78°C. The electrophile was then added dropwise, the mixture was warmed slowly to room temperature, heated to reflux and the procedure continued as above.
26. A. Padwa, J. R. Gasdaska, M. Tomas, N. J. Turro, Y. Cha and I. R. Gould, J. Am. Chem. Soc., 1986, 108, 6739.