Synthesis of N-substituted 2-arylpyrroles by the reaction of (η2-imine)titanium complexes with 3,3-diethoxypropyne

Tetrahedron Letters

Volumn 47, Issue 35, 2006, Pages 6209-6212

  Ohkubo, Mutsumi ^a   Hayashi, Daisuke ^a   Oikawa, Daisuke ^a   Fukuhara, Kouki ^b   Okamoto, Sentaro ^a   Sato, Fumie ^b  

^a KANAGAWA UNIVERSITY   (Japan)

^b TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLE DERIVATIVE; TITANIUM DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; MOLECULAR DYNAMICS; SUBSTITUTION REACTION;

EID: 33746322420     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.06.152     Document Type: Article

References (33)

1. Sato F., Urabe H., and Okamoto S. Chem. Rev. 100 (2000) 2835-2886
2. Kulinkovich O.G., and de Meijere A. Chem. Rev. 100 (2000) 2789-2834
3. Eisch J.J. J. Organomet. Chem. 617-618 (2001) 148-157
4. Sato F., and Okamoto S. Adv. Synth. Catal. 343 (2001) 759-784
5. Sato F., and Urabe H. In: Marek I. (Ed). Titanium and Zirconium in Organic Synthesis (2002), Wiley-VCH, Weinheim, Germany 319-354
6. 2 complexes, see:. Gao Y., Yoshida Y., and Sato F. Synlett (1997) 1353
7. Fukuhara K., Okamoto S., and Sato F. Org. Lett. 5 (2003) 2145
8. Quntar A.A.A.A., Dembitsky V.M., and Srebnik M. Org. Lett. 5 (2003) 357
9. For recent examples, see:. Gorin D.J., Davis N.R., and Toste F.D. J. Am. Chem. Soc. 127 (2005) 11260
10. Kamijo S., Kanazawa C., and Yamamoto Y. J. Am. Chem. Soc. 127 (2005) 9260
11. Dhawan R., and Arndtsen B.A. J. Am. Chem. Soc. 126 (2004) 468
12. Siriwardana A.I., Kathriarchchi K.K.A.D.S., Nakamura I., Gridnev I.D., and Yamamoto Y. J. Am. Chem. Soc. 126 (2004) 13898
13. Dhawan R., and Arndtsen B.A. J. Am. Chem. Soc. 126 (2004) 468
14. Ramanathan B., Keith A.J., Armstrong D., and Odom A.L. Org. Lett. 6 (2004) 2957
15. Gabriele B., Salerno G., and Fazio A. J. Org. Chem. 68 (2003) 7853
16. Nishibayashi Y., Yoshikawa M., Inada Y., Milton M.D., Hidai M., and Uemura S. Angew. Chem., Int. Ed. 42 (2003) 2681
17. Wang Y., and Zhu S. Org. Lett. 5 (2003) 745
18. For reviews see:. Gilchrist T.L. J. Chem. Soc., Perkin Trans. 1 (1999) 2849-2866
19. In: Jones R.A. (Ed). Pyrroles, Chemistry of Heterocyclic Compounds Vol. 48 (1990), Wiley, New York
20. In: Jones R.A. (Ed). Pyrroles, Part II (1992), Wiley, New York
21. Thompson R.B. FASEB J. 15 (2001) 1671
22. Muchowski J.M. Adv. Med. Chem. 1 (1992) 109
23. Cozzi P., and Mongelli N. Curr. Pharm. Des. 4 (1998) 181
24. Fürstner A., Szillat H., Gabor B., and Mynott R. J. Am. Chem. Soc. 120 (1998) 8305
25. Chavatte P., Yous S., Marot C., Baurin N., and Lesieur D. J. Med. Chem. 44 (2001) 3223 and references cited therein
26. In: Skotheim T.A., Elsenbaumer R.L., and Reynolds J.R. (Eds). Handbook of Conducting Polymers. 2nd ed. (1998), Marcel Dekker, New York
27. 2H-2a was prepared according to the procedure illustrated in the following scheme:{A figure is presented}
28. 3 (0.2 mL), NaF (∼1 g) and Celite (∼1 g), the mixture was filtered through a pad of Celite. The filtrate was concentrated in vacuo and chromatographed on silica gel to give 1a (158 mg) in 68% yield.
29. 2a
30. 3) of 6. Compound 6a: (500 MHz): δ 5.17 (s, 2H), 6.30 (d, J = 2.3 Hz, 2H), 6.76 (t, J = 2.4 Hz, 1H), 7.02-7.07 (m, 2H), 7.25-7.37 (m, 8H). Compound 6b: (300 MHz): δ 5.14 (s, 2H), 6.29-6.31 (m, 2H), 6.78-6.80 (m, 1H), 7.0-7.49 (m, 9H). Compound 6c: (500 MHz): δ 0.81 (t, J = 7.5 Hz, 3H), 1.62-1.69 (m, 2H), 3.87 (t, J = 6.5 Hz, 2H), 6.16-6.19 (m, 2H), 6.76 (d, J = 2.3 Hz, 1H), 7.25 (d, J = 7.3 Hz, 2H), 7.51 (d, J = 7.3 Hz, 2H). Compound 6d: (300 MHz): δ 3.64 (s, 3H), 3.89 (s, 3H), 5.15 (s, 2H), 6.26 (dd, J = 1.8, 3.6 Hz, 1H), 6.30 (dd, J = 2.7, 3.6 Hz, 1H), 6.76-7.36 (m, 9H). Compound 6e: (270 MHz): δ 3.84 (s, 3H), 3.92 (s, 3H), 5.51 (s, 1H), 6.86 (d, J = 1.8 Hz, 1H), 7.34-7.46 (m, 17H). Compound 6f: (300 MHz): δ 5.19 (s, 1H), 6.33 (dd, J = 2.7, 3.6 Hz, 1H), 6.38 (dd, J = 2.1, 3.6 Hz, 1H), 6.83 (dd, J = 1.8, 2.7 Hz, 1H), 7.05-7.10 (m, 2H), 7.25-7.36 (m, 3H), 7.44 (d, J = 7.8 Hz, 2H), 7.59 (d, J = 7.8 Hz, 2H). Compound 6g: (270 MHz): δ 3.52 (s, 3H), 3.51 (m, 4H), 6.21 (m, 2H), 6.83 (dd, J = 1.8, 2.7 Hz, 1H), 7.44 (d, J = 7.8 Hz, 2H), 7.59 (d, J = 7.8 Hz, 2H). Compound 6h: (300 MHz): δ 5.29 (s, 2H), 6.19 (d, J = 3.3 Hz, 1H), 6.24 (dd, J = 2.7, 3.6 Hz, 1H), 6.36 (dd, J = 1.8, 3.3 Hz, 1H), 6.48 (dd, J = 1.8, 3.9 Hz, 1H), 6.73 (dd, J = 1.8, 2.7 Hz, 1H), 7.03-7.34 (m, 5H), 7.38 (dd, J = 0.6, 2.4 Hz, 1H). Compound 6i: (500 MHz): δ 3.77 (s, 3H), 5.21 (s, 2H), 6.21-6.22 (m, 2H), 6.37 (d, J = 1.7 Hz, 1H), 6.48 (d, J = 1.8 Hz, 1H), 6.70 (t, J = 1.8 Hz, 1H), 6.83 (d, J = 7.1 Hz, 2H), 7.01 (d, J = 8.3 Hz, 2H), 7.40 (d, J = 1.2 Hz, 1H). Compound 6j: (300 MHz): δ 4.86 (s, 2H), 6.31 (dd, J = 1.8, 3.6 Hz, 1H), 6.37 (dd, J = 2.7, 3.6 Hz, 1H), 6.83-6.88 (m, 3H), 7.14-7.21 (m, 3H), 7.35-7.52 (m, 4H), 7.75-7.90 (m, 3H).
31. Indole synthesis from 3,3-diethoxypropyne, see:. Zhang H.-C., Ye H., Moretto A.F., Brumfield K.K., and Maryanoff B.E. Org. Lett. 2 (2000) 89
32. Larock R.C., Yum E.K., and Refvik M.D. J. Org. Chem. 63 (1998) 7652
33. Sakamoto T., Kondo Y., Iwashita S., Nagano T., and Yamanaka H. Chem. Pharm. Bull. 36 (1988) 1305