Aminoalkylations of esters, sulfones, sulfoxides, alkylated pyridines, and nitriles with in situ generated iminium ions

Synthesis

Volumn , Issue 20, 2006, Pages 3377-3388

  Katritzky, Alan R ^a   Idzik, Krzysztof R ^a,b   Abdel Fattah, Ashraf A A ^a,c   Soloducho, Jadwiga ^b   Steel, Peter J ^d  

^a University of Florida ^*  (United States)

^b WROCLAW UNIVERSITY OF TECHNOLOGY   (Poland)

^c BENHA UNIVERSITY   (Egypt)

^d UNIVERSITY OF CANTERBURY   (New Zealand)

Author keywords

amino esters; aminoalkyl cyanides; aminoalkyl sulfones; Benzotriazoles; Pyridines

Indexed keywords

ALDEHYDES; ALKYLATION; AMINES; IONS; NITROGEN COMPOUNDS; REACTION KINETICS; SULFUR COMPOUNDS;

AMINOALKYLATIONS; NITRILES; PYRIDINES; SULFONES; SULFOXIDES;

ESTERS;

ALPHA (BETA AMINOALKYL)PYRIDINE; BENZOTRIAZOLE DERIVATIVE; BETA AMINO CARBOXYLIC ESTER; BETA AMINOALKYL CYANIDE; BETA AMINOALKYL SULFONE; BETA AMINOALKYLSULFOXIDE; CYANIDE; ESTER DERIVATIVE; GAMMA (BETA AMINOALKYL)PYRIDINE; N (ALPHA AMINOALKYL)BENZOTRIAZOLE; NITRILE; PYRIDINE DERIVATIVE; SULFONE DERIVATIVE; SULFOXIDE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; MEDICAL RESEARCH; SYNTHESIS;

EID: 33750586143     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-949463     Document Type: Article

References (81)

1. (a) Tramontini, M.; Angiolini, L. Chemistry Uses; CRC Press: Boca Raton / FL, 1994.
2. (b) Tramontini, M.; Angiolini, L. Tetrahedron 1990, 46, 1791.
3. (c) Traxler, P.; Trinks, U.; Buchdunger, E.; Mett, H.; Meyer, T.; Müller, M.; Regenass, U.; Rösel, J.; Lydon, N. J. Med. Chem. 1995, 38, 2441.
4. (d) Lóránd, T.; Ösz, E.; Kispál, G.; Nagy, G.; Weckert, E.; Luebbert, D.; Meents, A.; Kocsis, B.; Prókai, L. ARKIVOC 2004, (vii), 34.
5. (e) Sapi, J.; Laronze, J.-Y. ARKIVOC 2004, (vii), 208.
6. Tramontini, M. Synthesis 1973, 703.
7. (a) Arend, M.; Westermann, B.; Risch, N. Angew. Chem. Int. Ed. 1998, 37, 1044.
8. (b) Piper, S.; Risch, N. ARKIVOC 2003, (i), 86.
9. (a) Katritzky, A. R.; Lan, X.; Yang, J. Z.; Denisko, O. V. Chem. Rev. 1998, 98, 409.
10. (b) Katritzky, A. R.; Manju, K.; Singh, S. K.; Meher, N. K. Tetrahedron 2005, 61, 2555.
11. Katritzky, A. R.; Yannakopoulou, K.; Kuzmierkiewicz, W.; Aurrecoechea, J. M.; Palenik, G. J.; Koziol, A. E.; Szczesniak, M.; Skarjune, R. J. Chem. Soc., Perkin Trans. 1 1987, 2673.
12. (a) Katritzky, A. R.; Yannakoponlou, K.; Lue, P.; Rasala, D.; Urogdi, L. J. Chem. Soc., Perkin Trans. 1 1989, 225.
13. (b) Katritzky, A. R.; Nair, S. K.; Qiu, G. Synthesis 2002, 199.
14. Katritzky, A. R.; Yang, Z.; Lam, J. N. Tetrahedron 1992, 48, 4978.
15. Katritzky, A. R.; Saczewski, F. Gazz. Chim. Ital. 1990, 375.
16. Katritzky, A. R.; Harris, P. A. Tetrahedron 1990, 46, 987.
17. Katritzky, A. R.; Abdel-Fattah, A. A. A.; Tymoshenko, D. O.; Belyakov, S. A.; Ghiviriga, I.; Steel, P. J. J. Org. Chem. 1999, 64, 6071.
18. Katritzky, A. R.; Fan, W.-Q.; Long, Q.-H. Synthesis 1993, 229.
19. Katritzky, A. R.; Abdel-Fattah, A. A. A.; Steel, P. J. Tetrahedron Lett. 2006, 47, 1465.
20. Katritzky, A. R.; Rachwal, S.; Rachwal, B.; Steel, P. J. J. Org. Chem. 1992, 57, 4932.
21. Katritzky, A. R.; Pilarski, B.; Urogdi, L. Org. Prep. Proced. Int. 1989, 21, 135.
22. (a) Ma, J.-A. Angew. Chem. Int. Ed. 2003, 42, 4290.
23. (b) Cardillo, G.; Tomasini, C. Chem. Soc. Rev. 1996, 25, 117.
24. (a) Tang, W.; Zhang, X. Org. Lett. 2002, 4, 4159.
25. (b) Zhou, Y.-G.; Tang, W.; Wang, W.-B.; Li, W.; Zhang, X. J. Am. Chem. Soc. 2002, 124, 4952.
26. (c) Hsiao, Y.; Rivera, N. R.; Rosner, T.; Krska, S. W.; Njolito, E.; Wang, F.; Sun, Y.; Armstrong, J. D. III; Grabowski, E. J. J.; Tillyer, R. D.; Spinaler, F.; Malan, C. J. Am. Chem. Soc. 2004, 126, 9918.
27. (a) Wenzel, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 12964.
28. (b) Bernardi, L.; Gothelf, A. S.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2003, 68, 2583.
29. (c) Akiyama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Angew. Chem. Int. Ed. 2004, 43, 1566.
30. Kobayashi, S.; Ishitani, H.; Komiyama, S.; Oniciu, A. R.; Katritzky, A. R. Tetrahedron Lett. 1996, 37, 3731.
31. Katritzky, A. R.; Shobana, N.; Harris, P. A. Tetrahedron Lett. 1990, 31, 3999.
32. (a) Wang, Q.; Dau, M.-E. T. H.; Sasaki, N. A.; Potier, P. Tetrahedron 2001, 57, 6455.
33. (b) Lehman de Gaeta, L. S.; Czarniecki, M.; Spaltenstein, A. J. Org. Chem. 1989, 54, 4004.
34. Alonso, D. A.; Costa, A.; Mancheño, B.; Nájera, C. Tetrahedron 1997, 53, 4791.
35. DiPietro, D.; Borzilleri, R. M.; Weinreb, S. M. J. Org. Chem. 1994, 59, 5856.
36. Pauly, R.; Sasaki, N. A.; Potier, P. Tetrahedron Lett. 1994, 35, 237.
37. Paik, S.; White, E. H. Tetrahedron Lett. 1996, 37, 4663.
38. (a) de Blas, J.; Carretero, J. C.; Dominguez, E. Tetrahedron Lett. 1994, 35, 4603.
39. (b) Pesenti, C.; Arnone, A.; Arosio, P.; Frigerio, M.; Meille, S. V.; Panzeri, W.; Viani, F.; Zanda, M. Tetrahedron Lett. 2004, 45, 5125.
40. Wu, J. C.; Pathak, T.; Tong, W.; Vial, J. M.; Remaud, G.; Chattopadhyaya, J. Tetrahedron 1988, 37, 6705.
41. (a) Carretero, J. C.; Arrayás, R. G.; de Gracia, I. S. Tetrahedron Lett. 1997, 38, 8537.
42. (b) Kumareswaran, R.; Hassner, A. Tetrahedron: Asymmetry 2001, 12, 2269.
43. (a) Ermolenko, L.; Sasaki, N. A.; Potier, P. Tetrahedron Lett. 1999, 40, 5187.
44. (b) Ermolenko, L.; Sasaki, N. A.; Potier, P. J. Chem. Soc., Perkin Trans. 1 2000, 2465.
45. (a) Rao, A. V. R.; Gurjar, M. K.; Pal, S. Tetrahedron Lett. 1995, 36, 2505.
46. (b) Nakamura, H.; Wu, H.; Kobayashi, J.; Kobayashi, M.; Ohizumi, Y.; Hirata, Y. J. Org. Chem. 1985, 50, 2494.
47. (c) Ichikawa, Y. Tetrahedron Lett. 1988, 29, 4957.
48. Caldwell, J. J.; Craig, D.; East, S. P. Synlett 2001, 1602.
49. (a) Balasubramanian, T.; Hassner, A. Tetrahedron: Asymmetry 1998, 9, 2201.
50. (b) Kumareswaran, R.; Balasubramanian, T.; Hassner, A. Tetrahedron Lett. 2000, 47, 8157.
51. (a) Carretero, J. C.; Arrayás, R. G. Synlett 1999, 49.
52. (b) Carretero, J. C.; Arrayás, G. J. Org. Chem. 1998, 63, 2993.
53. (a) Enders, D.; Muller, S. F.; Raabe, R. G.; Runsink, J. Eur. J. Org. Chem. 2000, 879.
54. (b) Gnanadeepam, M.; Selvaraj, S.; Perumal, S.; Renuga, S.; Selvaraj, S. Phosphorus, Sulfur Silicon Relat. Elem. 2002, 177, 431.
55. (c) Aben, R. W. M.; Braverman, S.; Scheeren, H. W. Eur. J. Org. Chem. 2003, 894.
56. Fustero, S.; Soler, J. G.; Bartolomé, A.; Roselló, M. S. Org. Lett. 2003, 5, 2707.
57. Carreño, M. C. Chem. Rev. 1995, 95, 1717.
58. (a) Kleemann, A. Pharmaceutical Substances, 3rd ed.; Georg Thieme Verlag: Stuttgart, 1999.
59. (b) Michael, A. B.; Rose, M. A. EP 0092903, 1983; Chem. Abstr. 1984, 100, 68182.
60. Schöllkopf, K.; Watchtel, H. US 4925854, 1990; Chem. Abstr. 1989, 111, 497237.
61. Sakamoto, T.; Nagata, H.; Kondo, Y.; Sato, K.; Yamanaka, H. Chem. Pharm. Bull. 1984, 32, 4866.
62. Reich, H. E.; Levine, R. J. Am. Chem. Soc. 1955, 77, 4913.
63. Hallberg, A.; Gronowitz, S. Chem. Scr. 1980, 16, 42.
64. Juergen, T.; Lothard, F.; Juergen, M.; Knut, O. Eur. Pat. Appl. EP 568873 A2, 1993; Chem. Abstr. 1994, 120, 58347.
65. Crovetti, A. J.; Forest, L.; Neundorf, M. V.; Bluff, L. US 3457294, 1969; Chem. Abstr. 1970, 72, 3259.
66. Zhukov, I. N.; Perov, P. A.; Ushakova, Z. V.; Shatava, O. S. SU 1500643 A1, 1989; Chem. Abstr. 1990, 112, 23177.
67. Novak, J. CS 265181 B1, 1989; Chem. Abstr. 1991, 114, 165722.
68. Preiml, M.; Hönig, H.; Klempier, N. J. Mol. Catal. B: Enzym. 2004, 29, 115.
69. Mukerjee, A. K.; Srivastava, R. C. Synthesis 1973, 327.
70. Hodgson, D. R. W.; Sanderson, J. M. Chem. Soc. Rev. 2004, 33, 422.
71. Fülöp, F. Chem. Rev. 2001, 101, 2181.
72. Picard, J.-P.; Fortis, F.; Grelier, S. J. Organomet. Chem. 2003, 686, 306.
73. Ishii, K.; Hakamada, S.; Nagano, M.; Noji, M.; Sugiyama, S.; Kotera, M.; Sakamoto, M. J. Chem. Soc., Perkin Trans. 1 2002, 1592.
74. (a) Wu, J.; Hou, X.-L.; Dai, L.-X. J. Org. Chem. 2000, 65, 1344.
75. (b) Farràs, J.; Gines̀ta, X.; Sutton, P. W.; Taltavull, J.; Egeler, F.; Romea, P.; Urpí, F.; Vilarrasa, J. Tetrahedron 2001, 57, 7665.
76. (c) Houdary, B. M.; Kulandaivelu, J.; Likhar, P. R.; Mannepalli, L. K.; Bojja, S.; Kotamarthi, B.; Sanyasi, S. PCT Int. Appl. WO 2004050606 A1, 2004; Chem. Abstr. 2004, 141, 54070.
77. Sun, P.; Zhang, Y. Synth. Commun. 1997, 27, 3175.
78. (a) Caputo, R.; Cassano, E.; Longobardo, L.; Palumbo, G. Tetrahedron 1995, 51, 12337.
79. (b) Dallaire, C.; Arya, P. Tetrahedron Lett. 1998, 39, 5129.
80. Carlier, P. R.; Lo, K. M. J. Org. Chem. 1994, 59, 4053.
81. Carlier, P. R.; Lo, K. M.; Lo, M. M-C.; Williams, I. D. J. Org. Chem. 1995, 60, 7511.