An Efficient synthesis of 2-aminofuran-3-carbonitriles via cascade Stetter-γ-ketonitrile cyclization reaction catalyzed by N-heterocyclic carbene

Synlett

Volumn , Issue 8, 2011, Pages 1133-1136

  Liu, Peng ^a   Lei, Min ^a   Ma, Lei ^a   Hu, Lihong ^a,b  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

2 aminofuran; cascade reaction; N heterocyclic carbenes (NHCs); Stetter reaction; umpolung

Indexed keywords

2 AMINOFURAN 3 CARBONITRILE; 2 BENZYLIDENEMALONONITRILE; 2 CHLOROBENZALDEHYDE; 4 CHLOROBENZALDEHYDE; ACETONITRILE; ACYLIDENEMALONONITRILE; ALCOHOL; ALDEHYDE; BENZALDEHYDE; BENZALDEHYDE DERIVATIVE; CARBENE; FURAN DERIVATIVE; GAMMA KETONITRILE; HETEROCYCLIC COMPOUND; METHANOL; N HETEROCYCLIC CARBENE; NITRILE; TETRAHYDROFURAN; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; CYCLIZATION; METHODOLOGY; ROOM TEMPERATURE; SOLVENT EFFECT; STETTER GAMMA KETO NITRILE CYCLIZATION; SUBSTITUTION REACTION;

EID: 79955665034     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1259945     Document Type: Article

References (51)

1. Arduengo A J. III., Harlow R L., Kline M K., J. Am. Chem. Soc. 1991 113 9704
2. Marion N, Díez-González S, Nolan S P., Angew. Chem. Int. Ed. 2007 46 2988.
3. Angew. Chem. 2007, 119, 3046
4. Enders D, Niemeier O, Henseler A, Chem. Rev. 2007 107 5606
5. Nair V, Vellalath S, Babu B P., Chem. Soc. Rev. 2008 37 2691
6. Moore J L., Rovis T, Top. Curr. Chem. 2010 291 77
7. Sheehan J, Hunneman D H., J. Am. Chem. Soc. 1966 88 3666
8. Stetter H, Schreckenberg M, Angew. Chem., Int. Ed. Engl. 1973 12 81
9. Angew. Chem. 1973, 85, 89.
10. Stetter H, Rmsch R Y., Kuhlmann H, Synthesis 1976 733
11. Heck R, Henderson A P., Köhler B, Rtey J, Golding B T., Eur. J. Org. Chem. 2001 14 2623
12. Enders D, Kallfass U, Angew. Chem. Int. Ed. 2002 41 1743
13. Angew. Chem. 2002, 114, 1822
14. OToole S E., Rose C A., Gundala S, Zeitler K, Connon S J., J. Org. Chem. 2011 76 347
15. Stetter H, Angew. Chem., Int. Ed. Engl. 1976 15 639
16. Angew. Chem.; 1976, 88, 695
17. Stetter H, Kuhlmann H, Org. React. (N.Y.) 1991 40 407
18. Hachisu Y, Bode J W., Suzuki K, J. Am. Chem. Soc. 2003 125 8432
19. Burstein C, Glorius F, Angew. Chem. Int. Ed. 2004 43 6205
20. Angew. Chem. 2004, 116, 6331
21. Enders D, Niemeier O, Balensiefer T, Angew. Chem. Int. Ed. 2006 45 1463
22. Angew. Chem. 2006, 118, 1491
23. Burstein C, Tschan S, Xie X, Glorius F, Synthesis 2006 2418
24. Takikawa H, Hachisu Y, Bode J W., Suzuki K, Angew. Chem. Int. Ed. 2006 45 3492
25. Angew. Chem. 2006, 118, 3572
26. Li Y, Feng Z, You S.-L, Chem. Commun. 2008 226
27. Hirano K, Piel I, Glorius F, Adv. Synth. Catal. 2008 350 984
28. Liu Y.-K, Li R, Yue L, Li B.-J, Chen Y.-C, Wu Y, Ding L.-S, Org. Lett. 2006 8 1521
29. Yadav L D. S., Rai V K., Singh S, Singh P, Tetrahedron Lett. 2010 51 1657
30. Mattson A E., Zuhl A M., Reynolds T E., Scheidt K A., J. Am. Chem. Soc. 2006 128 4932
31. Murry J A., Franz D E., Soheil A, Tillyer R E., Grabowski J J., Reider P J., J. Am. Chem. Soc. 2001 123 9696
32. Mennen S M., Gipson J D., Kim Y R., Miller S J., J. Am. Chem. Soc. 2005 127 1654
33. Li G.-Q, Dai L.-X, You S.-L, Chem. Commun. 2007 852
34. For reviews on cascade reactions, see:, Tietze L F., Chem. Rev. 1996 96 115
35. Fogg D E., dosSantos E N., Coord. Chem. Rev. 2004 248 2365
36. Chapman C J., Frost C G., Synthesis 2007 1
37. Enders D, Grondal C, Httl M R. M., Angew. Chem. Int. Ed. 2007 46 1570
38. Angew. Chem. 2007, 119, 1590
39. Tietze L F., Brasche G, Gericke K, Domino Reactions in Organic Synthesis Wiley-VCH Weinheim 2006
40. Christopher R.J.Pantos G.D.Angus J.M.Martin D.S.Angew. Chem. Int. Ed. 2009 48 7391
41. For recent examples, see:, Christopher R J., Pantos G D., Angus J M., Martin D S., Angew. Chem. Int. Ed. 2009 48 7391; Angew. Chem. 2009, 121, 7527
42. Sylvain B, Ross W C., David B B., Org. Lett. 2009 11 305
43. Sánchez-Larios E, Gravel M, J. Org. Chem. 2009 74 7536
44. Sánchez-Larios E, Holmes J M., Daschner [nl]C L., Gravel M, Org. Lett. 2010 12 5772
45. Sun F.-G, Huang X.-L, Ye S, J. Org. Chem. 2010 75 273
46. Xiao F, Lancelot J C., Prunier H, Rault S, J. Heterocycl. Chem. 1996 33 2007
47. Abderhamid A O., Negm A M., Abbas I M., J. Prakt. Chem. 1989 331 31
48. Gewald K, Chem. Ber. 1966 99 1002
49. Jun J G., Bull. Korean Chem. Soc. 1996 17 676
50. Watanuki S, Sakamoto S, Harada H, Kikuchi K, Kuramochi T, Kawaguchi K, Okazaki T, Tsukamoto S, Heterocycles 2004 62 127
51. Heravi M M., Tehrani M H., Bakhtiari K, Oskooie H A., J. Chem. Res. 2006 9 561