Efficient synthesis of 2-imino-1,2-dihydroquinolines and 2-imino-thiochromenes via copper-catalyzed domino reaction

Tetrahedron

Volumn 64, Issue 3, 2008, Pages 487-492

  Cui, Sun Liang ^a   Wang, Jing ^a   Wang, Yan Guang ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

2 Imino 1,2 dihydroquinolines; 2 Imino thiochromenes; Alkynes; Domino reaction; Sulfonyl azides

Indexed keywords

CHROMENE DERIVATIVE; COPPER; DIHYDROQUINOLINE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; MASS SPECTROMETRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS; X RAY ANALYSIS;

EID: 36549046139     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.11.025     Document Type: Article

References (38)

1. For a review, see:. Katritzky A.R., Rachwal S., and Rachwal B. Tetrahedron 52 (1996) 15031-15070
2. For examples of natural products, see:
3. Witherup K.M., Ransom R.W., Graham A.C., Bernard A.M., Salvatore M.J., Lumma W.C., Anderson P.S., Pitzenberger S.M., and Varga S.L. J. Am. Chem. Soc. 117 (1995) 6682-6685
4. Kariba R.M., Houghton P.J., and Yenesew A. J. Nat. Prod. 65 (2002) 566-569
5. Rakotoson J.H., Fabre N., Jacquemond-Collet I., Hannedouche S., Fouraste I., and Moulis C. Planta Med. 64 (1998) 762-763
6. For recent examples, see:
7. Rezgui F., Mangeney P., and Alexis A. Tetrahedron Lett. 40 (1999) 6241-6244
8. Evans P.A., Robinson J.E., and Moffett K.K. Org. Lett. 3 (2001) 3269-3271
9. Pastine S.J., Youn S.-W., and Sames D. Tetrahedron 59 (2003) 8859-8868
10. Pohlhaus P.D., Bowman R.K., and Johnson J.S. J. Am. Chem. Soc. 126 (2004) 2294-2295
11. Lu G.-L., and Malinakova H.C. J. Org. Chem. 69 (2004) 4701-4715
12. Skraup Z.H. Chem. Ber. 13 (1880) 2086-2087
13. Wahren M. Tetrahedron 20 (1964) 2773-2780
14. Bischler A., and Napieralski B. Chem. Ber. 26 (1893) 1903-1908
15. Fodor G., and Nagubandi S. Tetrahedron 36 (1980) 1279-1300
16. Arduini A., Bigi F., Casiraghi G., Casnati G., and Sartori G. Synthesis (1981) 975-976
17. Luo Y.M., Li Z.G., and Li C.J. Org. Lett. 7 (2005) 2675-2678
18. Liu X.Y., Ding P., Huang J.S., and Che C.M. Org. Lett. 9 (2007) 2645-2648
19. Ranu B.C., Hajra A., Dey S.S., and Jana U. Tetrahedron 59 (2003) 813-819
20. Raitio K.H., Savinainen J.R., Vepsäläinen J., Laitinen J.T., Poso A., Järvinen T., and Nevalainen T. J. Med. Chem. 49 (2006) 2022-2027
21. Li H., Wang J., Xie H.X., Zu L.S., Jiang W., Duesler E.N., and Wang W. Org. Lett. 9 (2007) 965-968
22. Cui S.L., Lin X.F., and Wang Y.G. Org. Lett. 8 (2006) 4517-4520
23. Ingall A.H. In: Boulton A.S., and McKkillop A. (Eds). Comprehensive Heterocyclic Chemistry II Vol. 5 (1996), Pergamon, Oxford 501
24. Rogier, D. J., Jr.; Carter, J. S.; Talley, J. J. WO 2001049675, 2001.
25. Brown M.J., Carter P.S., Fenwick A.E., Fosberry A.P., Hamprecht D.W., Hibbs M.J., Jarvest R.L., Mensah L., Milner P.H., O'Hanlon P.J., Pope A.J., Richardson C.M., West A., and Witty D.R. Bioorg. Med. Chem. Lett. 12 (2002) 3171-3174
26. Quaglia W., Pigini M., Piergentili A., Giannella M., Gentili F., Marucci G., Carrieri A., Carotti A., Poggesi E., Leonardi A., and Melchiorre C. J. Med. Chem. 45 (2002) 1633-1643
27. van Vliet L.A., Rodenhuis N., Dijkstra D., Wikstrom H., Pugsley T.A., Serpa K.A., Meltzer L.T., Heffner T.G., Wise L.D., Lajiness M.E., Huff R.M., Svensson K., Sundell S., and Lundmark M. J. Med. Chem. 43 (2000) 2871-2882
28. Wang W., Li H., Wang J., and Zu L.S. J. Am. Chem. Soc. 128 (2006) 10354-10355
29. For the selected examples for reduction of azides to amines using mercaptan as a reductant, see:
30. Savin K.A., Woo J.C.G., and Danishefsky S.J. J. Org. Chem. 64 (1999) 4183-4186
31. Lee J.W., and Fuchs P.L. Org. Lett. 1 (1999) 179-181
32. Benati L., Bencivenni G., Leardini R., Minozzi M., Nanni D., Scialpi R., Spagnolo P., and Zanardi G. J. Org. Chem. 71 (2006) 5822-5825
33. Long D.D., Smith M.D., Marquess D.G., Laridge T.D.W., and Fleet G.W.J. Tetrahedron Lett. 39 (1998) 9293-9296
34. Meldal M., Juliano M.A., and Jansson A.M. Tetrahedron Lett. 38 (1997) 2531-2534
35. Bae I., Han H., and Chang S. J. Am. Chem. Soc. 127 (2005) 2038-2039
36. Cho S.H., Yoo E.J., Bae I., and Chang S. J. Am. Chem. Soc. 127 (2005) 16046-16047
37. Cassidy M.P., Raushel J., and Fokin V.V. Angew. Chem., Int. Ed. 45 (2006) 3154-3157
38. Whiting M., and Fokin V.V. Angew. Chem., Int. Ed. 45 (2006) 3157-3161