Application of the Pictet-Spengler reaction to aryl amine substrates linked to deactivated aromatic heterosystems

Tetrahedron

Volumn 64, Issue 37, 2008, Pages 8676-8684

  Saha, B ^a   Sharma, S ^a   Sawant, D ^a   Kundu, B ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

Deactivated ring; Pictet Spengler reaction; Quinoxaline; Tetrazole; Triazole

Indexed keywords

AROMATIC AMINE; AROMATIC COMPOUND; QUINOXALINE DERIVATIVE; TETRAZOLE DERIVATIVE; TRIAZOLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; PICTET SPENGLER REACTION; PRIORITY JOURNAL; SYNTHESIS;

EID: 48049111168     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.07.003     Document Type: Article

References (89)

1. Pictet A., and Spengler T. Ber. Dtsch. Chem. Ges. 44 (1911) 2030-2036
2. Kawasaki T., and Higuchi K. Nat. Prod. Rep. 22 (2005) 761-793
3. Allen J.R., and Holmstedt B.R. Phytochemistry 19 (1979) 1573-1582
4. Braestrup C., Nielsen M., and Olsen C.E. Proc. Natl. Acad. Sci. U.S.A. 77 (1980) 2288-2292
5. Schlecker W., Huth A., Ottow E., and Mulzer J. Synthesis (1995) 1225-1227
6. Molina P., and Fresneda P.M. J. Chem. Soc., Perkin Trans. 1 (1988) 1819-1822
7. Molina P., Fresneda P.M., Zafra G.S., and Almendros P. Tetrahedron Lett. 35 (1994) 8851-8854
8. For reviews, see:
9. Royer J., Bonin M., and Micouin L. Chem. Rev. 104 (2004) 2311-2352
10. Nielsen T.E., Diness F., and Meldal M. Curr. Opin. Drug Discovery Dev. 6 (2003) 801-814
11. Cox E.D., and Cook J. Chem. Rev. 95 (1995) 1797-1842
12. Larghi E.L., Amongero M., Bracca A.B.J., and Kauffman T.S. Arkivoc xii (2005) 98-153
13. Czarnocki Z., MacLean D.B., and Szarek W.A. Can. J. Chem. 64 (1986) 2205-2210
14. Czarnocki Z., Suh D., MacLean D.B., Hultin P.G., and Szarek W.A. Can. J. Chem. 70 (1992) 1555-1561
15. Czarnocki Z., Mieckzkowsi J.B., Kiegiel J., and Araźny Z. Tetrahedron: Asymmetry 6 (1995) 2899-2902
16. Czarnocki Z., and Araźny Z. Heterocycles 51 (1999) 2871-2879
17. Rozwadowska M.D. Heterocycles 39 (1994) 903-931
18. Singh K., Deb P.K., and Venugopalan P. Tetrahedron 57 (2001) 7939-7949
19. Sandrin J., Soerens D., Mokry P., and Cook J.M. Heterocycles 6 (1977) 1133-1139
20. Dai W.M., Zhu H.J., and Hao X.J. Tetrahedron Lett. 37 (1996) 5971-5974
21. Czerwinski K.M., Deng L., and Cook J.M. Tetrahedron Lett. 33 (1994) 4721-4724
22. Zhang L.H., Bi Y.Z., Yu F.X., Menzia G., and Cook J.M. Heterocycles 34 (1992) 517-547
23. Ungemach F., DiPierro M., Weber R., and Cook J.M. J. Org. Chem. 46 (1981) 164-168
24. Jawdosiuk M., and Cook J.M. J. Org. Chem. 49 (1984) 2699-2701
25. Bonnet D., and Ganesan A. J. Comb. Chem. 4 (2002) 546-548
26. Wang H., and Ganesan A. Org. Lett. 1 (1999) 1647-1649
27. Zawadzka A., Leniewski A., Maurin J.K., Wojtasiewicz K., and Czarnocki Z. Org. Lett. 3 (2001) 997-999
28. Gremmen C., Wanner M.J., and Koommen G.J. Tetrahedron Lett. 42 (2001) 8885-8888
29. Gremmen C., Willemse B., Wanner M.J., and Koomen G.-J. Org. Lett. 2 (2000) 1955-1958
30. Hegedus A., and Hell Z. Tetrahedron Lett. 45 (2004) 8553-8555
31. Yen Y.-H., and Chu Y.-H. Tetrahedron Lett. 45 (2004) 8137-8140
32. Bianchi D.A., Rua F., and Kaufman T.S. Tetrahedron Lett. 45 (2004) 411-415
33. Taylor M.S., and Jacobsen E.N. J. Am. Chem. Soc. 126 (2004) 10558-10559
34. Gonzalez J.F., Cuesta E., and Avendano C. Tetrahedron 60 (2004) 6319-6326
35. Zhang X., Li X., Lanter J.C., and Sui Z. Org. Lett. 7 (2005) 2043-2046
36. Srinivasan N., and Ganesan A. Chem. Commun. (2003) 916-917
37. Yu J., Wearing X.Z., and Cook J.M. Tetrahedron Lett. 44 (2003) 543-547
38. Kane T.R., Ly C.Q., Kelly D.E., and Dener J.M. J. Comb. Chem. 6 (2004) 564-572
39. Zhou H., Liao X., and Cook J.M. Org. Lett. 6 (2004) 249-252
40. Nielsen T.E., and Meldal M. J. Comb. Chem. 7 (2005) 599-610
41. Soerens D., Sandrin J., Ungemach F., Mokry P., Wu G.S., Yamanaka E., Hutchins L., DiePierro M., and Cook J.M. J. Org. Chem. 44 (1979) 535-545
42. Woodward R.B., Cava M.P., Ollis W.D., Hunger A., Daeniker H.U., and Schenker K. Tetrahedron 19 (1963) 247-257
43. Jackson A.H., and Smith A.E. Tetrahedron 24 (1968) 403-413
44. Harrison D.M. Tetrahedron Lett. 22 (1981) 2501-2504
45. Kundu B., Sawant D., and Chhabra R. J. Comb. Chem. 7 (2005) 317-321
46. Kundu B., Sawant D., Partani P., and Kesarwani A.P. J. Org. Chem. 70 (2005) 4889-4892
47. Duggineni S., Sawant D., Saha B., and Kundu B. Tetrahedron 62 (2006) 3228-3241
48. Sharma S., Saha B., Sawant D., and Kundu B. J. Comb. Chem. 9 (2007) 783-792
49. Duncton M.A.J., Smith L.M., Burdzovic-Wizeman S., Burns A., Liu H., Mao Y., Wong W.C., and Kiselyov A.S. J. Org. Chem. 70 (2005) 9629-9631
50. Zheng L., Xiang J., Daang Q.D., and Bai X. J. Comb. Chem. 7 (2005) 813-815
51. David E., Pellet-Rostaing S., and Marc Lemaire M. Tetrahedron 63 (2007) 8999-9006
52. Wang X.L., Zheng X.F., Liu R.H., Reiner J., and Chang J.B. Tetrahedron 63 (2007) 3389-3394
53. Katritzky A.R. In: Katritzky, and Rees (Eds). Comprehensive Heterocyclic Chemistry Vol. 5 (1984) 41-110
54. Metzger J.V. In: Katritzky, and Rees (Eds). Comprehensive Heterocyclic Chemistry Vol. 6 (1984) 235-330
55. Stokker G.E. Tetrahedron Lett. 37 (1996) 5453-5456
56. Zhang L., Meier W., Wats E., Costello T.D., Ma P., Ensinger C.L., Rodgers J.M., Jacobson I.C., and Rajagopalan P. Tetrahedron Lett. 36 (1995) 8387-8390
57. Butler R.N. In: Katritzky, and Rees (Eds). Comprehensive Heterocyclic Chemistry Vol. 5 (1984) 816-818
58. Wahoff H. In: Katritzky, and Rees (Eds). Comprehensive Heterocyclic Chemistry Vol. 5 (1984) 697-700
59. Sarges R., Howard H.R., Brown R.C., Label L.A., and Seymour P.A. J. Med. Chem. 33 (1990) 2240-2254
60. Bailly C., Echepare S., Gargo F., and Raring M.J. Anti-Cancer Drug Des. 15 (1999) 219-222
61. Sakata G., Makino K., and Kurasawa Y. Heterocycles 27 (1998) 2481-2485
62. Buckle D.R., and Rockell C.J.M. J. Chem. Soc., Perkin Trans. 1 (1982) 627-630
63. Buckle D.R., Outred D.J., Rockell C.J.M., Smith H., and Spicer B.A. J. Med. Chem. 26 (1983) 251-254
64. Buckle D.R., Outred D.J., Rockell C.J.M., Smith H., and Spicer B.A. J. Med. Chem. 29 (1986) 2262-2267
65. Genin M.J., Allwine D.A., Anderson D.J., Barbachyn M.R., Emmert D.E., Garmon S.A., Graber D.R., Grega K.C., Hester J.B., Hutchinson D.K., Morris J., Reischer R.J., Ford C.W., Zurenko G.E., Hamel J.C., Schaadt R.D., Stapert D., and Yagi B.H. J. Med. Chem. 43 (2000) 953-970
66. Alvarez R., Velazquez S., San-Felix A., Aquaro S., De Clercq E., Perno C.F., Karlsson A., Balzarini J., and Camarasa M.J. J. Med. Chem. 37 (1994) 4185-4194
67. Kauer J.C., and Sheppard W.A. J. Org. Chem. 32 (1967) 3580-3592
68. LeBlanc B.W., and Jursic B.S. Synth. Commun. 28 (1998) 3591-3593
69. Markgraf J.H., and Sadighi J.P. Heterocycles 40 (1995) 583-586
70. Huisgen R. In: Padwa A. (Ed). 1,3-Dipolar Cycloaddition Chemistry (1984), Wiley, New York, NY
71. Bock V.D., Hiemstra H., and Maarseveen J.H.V. Eur. J. Org. Chem. (2006) 51-68
72. Rostovtsev V.V., Green L.G., Fokin V.V., and Sharpless K.B. Angew. Chem., Int. Ed. 114 (2002) 2708-2711
73. Chan T.R., Robert H., Sharpless K.B., and Fokin V.V. Org. Lett. 6 (2004) 2653-2855
74. Feldman A.K., Colasson B., and Fokin V.V. Org. Lett. 6 (2004) 3897-3899
75. Prasad A., Wim D., Fokin V.V., and Eycken E.V. Org. Lett. 6 (2004) 4223-4225
76. Rostovtsev V.V., Green L.G., Fokin V.V., and Sharpless K.B. Angew. Chem., Int. Ed. 41 (2002) 2596-2599
77. Tornoe C.W., Hristensen C., and Meldal M. J. Org. Chem. 67 (2002) 3057-3064
78. Horne W.S., Yadav M.K., Stout C.D., and Ghadiri M.R. J. Am. Chem. Soc. 126 (2004) 15366-15367
79. Manetsch R., Krasinski A., Radic Z., Raushel J., Taylor P., Sharpless K.B., and Kolb H.C. J. Am. Chem. Soc. 126 (2004) 12809-12818
80. Zhou Z., and Fahrni C.J. J. Am. Chem. Soc. 126 (2004) 8862-8863
81. Punna S., Kuzelka J., Wang Q., and Finn M.G. Angew. Chem., Int. Ed. 44 (2005) 2215-2220
82. Saha B., Sharma S., Sawant D., and Kundu B. Synlett (2007) 1591-1594
83. Nielsen T.E., and Meldal M. J. Org. Chem. 69 (2004) 3765-3773
84. Lanter J.C., and Sui Z. Org. Lett. 7 (2005) 2043-2046
85. Fernández D., Ahaidar A., Danelón D., Cironi P., Marfil M., Pérez O., Cuevas C., Albericio F., Joule J.A., and lvarez M.A. Monatsh. Chem. 135 (2004) 615-627
86. Brase S., Gil C., and Knepper K. Bioorg. Med. Chem. Lett. 10 (2002) 2415-2434
87. Balaban A.T., Oniciu D.C., and Katritzky A.R. Chem. Rev. 104 (2004) 2777-2812
88. Chen J.J., Fang H.Y., Duh C.Y., and Chen I.S. Planta Med. 71 (2005) 470-475
89. Nicolaou K.C., Baran P.S., Yong Y.L., and Sugita K. J. Am. Chem. Soc. 124 (2002) 2212-2220