A simple, cheap alternative to 'designer convertible isonitriles' expedited with microwaves

Tetrahedron Letters

Volumn 50, Issue 28, 2009, Pages 4054-4057

  Hulme, Christopher ^a   Chappeta, Shashi ^a   Dietrich, Justin ^a  

^a UNIVERSITY OF ARIZONA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BUTYLISONITRILE; ISONITRILE DERIVATIVE; NUCLEOPHILE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; MICROWAVE IRRADIATION; SYNTHESIS;

EID: 66149185540     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.04.095     Document Type: Article

References (64)

1. For relevant reviews see:. In: Zhu J., and Bienayme H. (Eds). Multicomponent Reactions (2005), Wiley-VCH, Weinheim
2. Ganem B. Acc. Chem. Res. 42 (2009) 463-472
3. Hulme C. Multicomponent Reactions (2005) 311-341
4. Dömling A. Chem. Rev. 106 (2006) 17-89
5. Hulme C., and Gore V. Curr. Med. Chem. 10 (2003) 51-80
6. Bienaymé H., Hulme C., Oddon G., and Schmitt P. Eur. J. Chem. 6 (2000) 3321-3329
7. Hulme C., and Nixey T. Curr. Opin. Drug Disc. Dev. 6 (2003) 921-929
8. Akritopoulou-Zanze I., and Djuric S.W. Heterocycles 73 (2007) 125-147
9. Banfi L., and Riva R. Org. React. 65 (2005)
10. El Kaim L., and Grimaud L. Tetrahedron 65 (2009) 2153-2171
11. Ugi I. Angew. Chem. 74 (1962) 9-22
12. Ugi I., and Steinbrucker C. Chem. Ber. 94 (1961) 734-742
13. Ugi I. Angew. Chem., Int. Ed. Engl. 1 (1962) 8
14. Ugi I., Domling A., and Horl W. Endeavor 18 (1994) 115
15. Rosendahl F.K., and Ugi I. Ann. Chem. 666 (1963) 65
16. Strocker A.M., Keating T.A., Tempest P.A., and Armstrong R.W. Tetrahedron Lett. 37 (1996) 1149-1152
17. Pirrung M.C., and Ghorai S. J. Am. Chem. Soc. 128 (2006) 11772-11773
18. Hulme C., Ma L., Cherrier M.-P., Romano J.J., Morton G., Duquenne C., Salvino J., and Labaudiniere R. Tetrahedron Lett. 41 (2000) 1883-1887
19. Kennedy A.L., Fryer A.M., and Josey J.A. Org. Lett. 4 (2002) 1167-1170
20. Chen J.J., Golebiowski A., Klopfenstein S.R., and West L. Tetrahedron Lett. 43 (2002) 4083-4085
21. Keating T.A., and Armstrong R.W. J. Am. Chem. Soc. 118 (1996) 2574-2583
22. Maison W., Schlemminger I., Westerhoff O., and Martens J. Bioorg. Med. Chem. 8 (2000) 1343-1360
23. Keating T.A., and Armstrong R.W.J. Am. Chem. Soc. 117 (1995) 7842-7843
24. Hulme C., Peng J., Morton G., Salvino J.M., Herpin T., and Labaudiniere R. Tetrahedron Lett. 39 (1998) 7227
25. Backes B.J., Virgflio A.A., and Ellman J.A. J. Am. Chem. Soc. 118 (1996) 3055
26. Kenner G.W., McDermott J.R., and Sheppard R.C. J. Chem. Soc., Chem. Commun. (1971) 636
27. Aplaviroc:. Habashita H., Kokubo M., Hamano S.-I., Hamanaka N., Toda M., Shibayama S., Tada H., Sagawa K., Fukushima D., Maeda K., and Mitsuya H. J. Med. Chem. 49 (2006) 4140-4152
28. Nishizawa R., Nishiyama T., Hisaichi K., Matsunaga N., Minamoto C., Habashita H., Takaoka Y., Toda M., Shibayama S., Tada H., Sagawa K., Fukushima D., Maeda K., and Mitsuya H. Bioorg. Med. Chem. Lett. 17 (2007) 727-731
29. Crabb C. AIDS 20 (2006) 641
30. Hulme C., Morrissette M., Volz F., and Burns C. Tetrahedron Lett. 39 (1998) 1113
31. Kappe C.O., and Dallinger D. Nat. Rev. Drug Disc. 5 (2006) 51-63
32. Blackburn C., Guan B., Fleming P., Shiosaki K., and Tsai S. Tetrahedron Lett. 39 (1998) 3635
33. Bienayme H., and Bouzid K. Angew. Chem., Int. Ed. 37 (1998) 2234
34. Groebke K., Weber L., and Mehlin F. Synlett (1998) 661-663
35. Zanchini C. Chem. Phys. 254 (2000) 187
36. Blackburn C. Tetrahedron Lett. 39 (1998) 5469-5472
37. Blackburn C., and Guan B. Tetrahedron Lett. 41 (2000) 1495
38. Hulme C., and Lee Y.-S. Mol. Div. 12 (2008) 1-15
39. Hulme C., Peng J., Louridas B., Menard P., Krolikowski P., and Kumar N.V. Tetrahedron Lett. 39 (1998) 8047
40. Nixey T., Tempest P., and Hulme C. Tetrahedron Lett. 43 (2002) 1637
41. Hulme C., Ma L., Romano J., Cherrier M.P., Salvino J., and Labaudiniere R. Tetrahedron Lett. 41 (2000) 1889
42. Hulme C., and Cherrier M.P. Tetrahedron Lett. 40 (1999) 5295
43. Hulme C., Ma L., and Labaudiniere R. Tetrahedron Lett. 41 (2000) 1509
44. Hulme C., Ma L., Romano J., Morton G., Tang S.-Y., Cherrier M.-P., Choi S., and Labaudiniere R. Tetrahedron Lett. 41 (2000) 1883
45. Hulme C., Peng J., Tang S.-Y., Burns C.J., Morize I., and Labaudiniere R. J. Org. Chem. 63 (1998) 8021-8023
46. Nixey T., and Hulme C. Tetrahedron Lett. 43 (2002) 6833-6835
47. Hulme C., Chappeta S., Griffith C., Lee Y.-S., and Dietrich J. Tetrahedron Lett. 50 (2009) 1939-1942
48. Tempest P., Ma V., Thomas S., Hua Z., Kelly M.G., and Hulme C. Tetrahedron Lett. 42 (2001) 4959-4962
49. Scifinder reagent costs were as follows: (a) n-butylisonitrile, 14, $132/5 g. (b) Cyclohexynl isonitrile, 1, 1060 EUR (∼$1300)/5 g. (c) 4-Phenylcyclohexynl isonitrile, 3, 1060 EUR (∼$1300)/5 g. (d) Prices for 2 and 4 were not available requiring specific custom synthesis.
50. 3): δ 172.12, 166.69, 136.91, 135.13, 133.79, 132.67, 131.96, 129.18 (2C), 129.02 (2C), 128.27, 126.93, 120.23, 71.83, 55.74, 27.93, 21.09, 19.99, 19.82.
51. Ribelin T.P., Judd A.S., Akritopoulou-Zanze I., Henry R.F., Cross J.L., Whittern D.N., and Djuric S.W. Org. Lett. 9 (2007) 5119-5122
52. Akritopoulou-Zanze I., Whitehead A., Waters J.E., Henry R.F., and Djuric S.W. Tetrahedron Lett. 48 (2007) 3549-3552
53. Akritopoulou-Zanze I., Whitehead A., Waters J.E., Henry R.F., and Djuric S.W. Org. Lett. 9 (2007) 1299-1302
54. Akritopoulou-Zanze I., Gracias V., and Djuric S.W. Tetrahedron Lett. 45 (2004) 8439-8441
55. Akritopoulou-Zanze I., Gracias V., Moore J.D., and Djuric S.W. Tetrahedron Lett. 45 (2004) 3421-3423
56. Basso A., Banfi L., Riva R., and Guanti G. J. Org. Chem. 70 (2005) 575-579
57. Basso A., Banfi L., Riva R., and Guanti G. Tetrahedron Lett. 45 (2004) 587-590
58. Basso A., Banfi L., Riva R., and Guanti G. Tetrahedron 62 (2006) 8830-8837
59. Banfi L., Basso A., Guanti G., and Riva R. Tetrahedron Lett. 45 (2004) 6637-6640
60. Ilyn A.P., Kuzovkova J.A., Shkirando A.M., and Ivachtchenko A.V. Heterocycl. Commun. 11 (2005) 523-526
61. Ilyin A., Kobak V., Dmitrieva I., Peregudova Y., Kustova V., Mishunina Y., Tkachenko S., and Ivachtchenko A. Synth. Commun. 36 (2006) 903-910
62. Ilyn A.P., Trifilenkov A.S., Tsirulnikov S.A., Kurashvily I.D., and Ivachtchenko A.V. J. Comb. Chem. 7 (2005) 806-808
63. Nenajdenko V.G., Reznichenko A.L., and Balenkova E.S. Tetrahedron 63 (2007) 3031-3041
64. Ilyin A.P., Trifilenkov A.S., Kurashvili I.D., Krasavin M., and Ivachtchenko A.V. J. Comb. Chem. 7 (2005) 360-363