New α-amido-α-aminonitrones as building blocks for constructing heterocyclic systems

Synthesis

Volumn , Issue 18, 2008, Pages 2977-2985

  Trzewik, Bartosz ^a   Ciez, Dariusz ^a   Hodorowicz, Maciej ^a   Stadnicka, Katarzyna ^a  

^a JAGIELLONIAN UNIVERSITY   (Poland)

Author keywords

Alkylation; Building blocks; Cyclisation; Heterocycles; Nitrones

Indexed keywords

AMINES;

ALKYLATION; BUILDING BLOCKS; CYCLISATION; HETEROCYCLES; NITRONES;

ACIDS;

2 ANILINO 2 [OXIDO(4 METHYLPHENYL)IMINO] N (4 METHYLPYRIDIN 2 YL)ACETAMIDE; 2 ANILINO 2 [OXIDO(PHENYL)IMINO] N (4 METHYLPYRIDIN 2 YL)ACETAMIDE; 2 ANILINO 2 [OXIDO(PHENYL)IMINO] N (4 NITROPYRIDIN 2 YL)ACETAMIDE; 2 ANILINO 2 [OXIDO(PHENYL)IMINO] N (5 METHYLPYRIDIN 2 YL)ACETAMIDE; 2 ANILINO 2 [OXIDO(PHENYL)IMINO] N PYRIDIN 2 YLACETAMIDE; 2 PHENYL 3 (PHENYLIMINO) 5 (PYRIDIN 2 YL) 1,2,5 OXADIAZINAN 4 ONE; 3 OXOBUTYRIC ACID N PYRIDIN 2 YLAMIDE DERIVATIVE; 5 (4 METHYLPYRIDIN 2 YL) 2 PHENYL 3 (PHENYLIMINO) 1,2,5 OXADIAZINAN 4 ONE; 5 (5 METHYLPYRIDIN 2 YL) 2 PHENYL 3 (PHENYLIMINO) 1,2,5 OXADIAZINAN 4 ONE; AMIDE; DIAZEPINE DERIVATIVE; N (4 METHYLPYRIDIN 2 YL) 2 (PHENYLAMINO) 2 (PHENYLIMINO)ETHAMIDE; N (5 NITROPYRIDIN 2 YL) 2 (PHENYLAMINO) 2 (PHENYLIMINO)ETHAMIDE; NITRONE DERIVATIVE; NITROSOBENZENE; QUINAZOLINONE DERIVATIVE; QUINOXALINE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; HYDROGEN BOND; INFRARED SPECTROSCOPY; X RAY DIFFRACTION;

EID: 53249111740     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1067236     Document Type: Article

References (118)

1. (a) Merino, P. In Science of Synthesis, Vol. 27; Padwa, A., Ed.; Thieme: Stuttgart, 2004, 511.
2. (b) Döpp, D.; Döpp, H. In Houben-Weyl Methoden der Organische Chemie, Vol. E14b/2; Klamann, D.; Hagemann, H., Eds.; Thieme: Stuttgart, 1990, 1533.
3. (c) Torsell, K. G. B. In Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis; VCH Inc.: New York, 1988.
4. (d) Cardona, F.; Goti, A. Angew. Chem. Int. Ed. 2005, 44, 7832.
5. (e) Brandi, A.; Cicchi, S.; Cordero, F. M.; Goti, A. Chem. Rev. 2003, 103, 1213.
6. (f) Goti, A.; Cordero, F. M.; Brandi, A. Top. Curr. Chem. 1996, 178, 1.
7. (g) Pellissier, H. Tetrahedron 2007, 63, 3235.
8. (h) Revueita, J.; Cicchi, S.; Goti, A.; Brandi, A. Synthesis 2007, 485.
9. (i) El Hassan, I.; Lauricella, R.; Tuccio, B. Central Eur. J. Chem. 2006, 4, 338.
10. (j) Mottley, C.; Mason, R. P. In Biological Magnetic Resonance, Vol. 8; Berliner, L. J.; Reuben, J., Eds.; Plenum Publishers: New York, 1989, 489.
11. (k) Tordo, P. In Electron Paramagnetic Resonance, Vol. 16; Gilbert, B. C.; Atherton, N. M.; Davies, M. J., Eds.; RSC Publishing: Cambridge, 1998, 116.
12. (l) Boruah, M.; Konwar, D.; Dutta, D. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2003, 42, 2112.
13. (m) Freisleben, A.; Schieberle, P.; Rychlik, M. J. Agric. Food Chem. 2002, 50, 4760.
14. (n) Saito, K.; Kawamura, A.; Kanie, T.; Ueda, Y.; Kondo, S. Heterocycles 2001, 55, 1071.
15. (a) Branco, P. S.; Prabhakar, S.; Lobo, A. M.; Williams, D. J. Tetrahedron 1992, 48, 6335.
16. (b) Warshaw, J. A.; Gallis, D. E.; Acken, B. J.; Gonzalez, O. J.; Crist, D. R. J. Org. Chem. 1989, 54, 1736.
17. (c) Baiocchi, L.; Picconi, G.; Palacco, G. J. Heterocycl. Chem. 1979, 16, 1477.
18. (d) Janzen, E. G.; Nutter, D. E. Magn. Reson. Chem. 1997, 35, 131.
19. (e) Clement, B.; Kaempchen, T. Arch. Pharm. (Weinheim, Ger.) 1987, 320, 566.
20. (f) Szantay, C.; Szabo, L. Chem. Ber. 1965, 98, 1013.
21. (g) Aurich, H. G. Chem. Ber. 1968, 101, 1761.
22. (a) Hodorowicz, M.; Stadnicka, K.; Trzewik, B.; Zaleska, B. Acta Crystallogr., Sect. E 2008, 64, o599.
23. (b) Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565.
24. (c) Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. J. Chem. Soc., Perkin Trans. 2 1987, 1.
25. (d) Guimanini, A. G.; Toniutti, N.; Verardo, G.; Merli, M. Eur. J. Org. Chem. 1999, 1, 141.
26. (a) Zaleska, B.; Bazanek, T.; Socha, R.; Karelus, M.; Grochowski, J.; Serda, P. J. Org. Chem. 2002, 67, 4526.
27. (b) Zaleska, B.; Socha, R.; Karelus, M.; Grochowski, J.; Serda, P.; Szneler, E. J. Org. Chem. 2003, 68, 2334.
28. (c) Zaleska, B.; Trzewik, B.; Karelus, M.; Serda, P. J. Chem. Res. 2007, 195.
29. (d) Zaleska, B.; Socha, R. Monatsh. Chem. 2000, 131, 1061.
30. Zaleska, B.; Socha, R.; Ciechanowicz-Rutkowska, M.; Pilati, T. Monatsh. Chem. 2000, 131, 1151.
31. Zaleska, B.; Trzewik, B.; Stodolak, E.; Grochowski, J.; Serda, P. Synthesis 2004, 2975.
32. (a) Diels, O.; Leeden, R. Chem. Ber. 1905, 38, 3363.
33. (b) Wright, J. B. J. Org. Chem. 1964, 29, 1620.
34. (a) Busch, R.; Kaemmerer, H. Chem. Ber. 1930, 63, 653.
35. (b) Gnihtel, H. Chem. Ber. 1970, 103, 3442.
36. (c) Gnihtel, H. Chem. Ber. 1971, 104, 1512.
37. (d) Kiersznicki, T.; Rajca, A. Pol. J. Chem. 1978, 52, 1827.
38. (e) Kamitori, Y. Heterocycles 2000, 53, 107.
39. (f) Amitina, S. A.; Grigor'ev, I. A.; Tikhonov, A. Ya. Russ. Chem. Bull. 2006, 55, 1046.
40. (g) Tselinskii, I. V.; Mel'nikova, S. F.; Pirogov, S. V. Russ. J. Org. Chem. 1997, 33, 1760.
41. (h) Gnichtel, H.; Moeller, B. Chem. Ber. 1981, 114, 3170.
42. (i) Riddell, F. G.; Turner, E. S. Tetrahedron 1979, 35, 1311.
43. (j) Coskun, N.; Sümengen, D. Synth. Commun. 1993, 23, 1699.
44. (k) Marwaha, A.; Bharatamb, P. V.; Mahajan, M. P. Tetrahedron Lett. 2005, 46, 8253.
45. (l) Marwaha, A.; Singh, P.; Mahajan, M. P. Tetrahedron 2006, 62, 5474.
46. (m) Gravestock, M. B.; Knight, D. W.; Malik, K. M. A.; Thornton, S. R. J. Chem. Soc., Perkin Trans. 1 2000, 3292; and references cited therein.
47. (n) Gravestock, M. B.; Knight, D. W.; Thornton, S. R. J. Chem. Soc., Chem. Commun. 1993, 169.
48. (o) Gouverneur, V.; Ghosez, L. Tetrahedron 1996, 52, 7585; and references cited therein.
49. (p) Coskun, N.; Tat, F.; Gueven, O. O. Synth. Commun. 1999, 29, 3889.
50. (q) Billert, T.; Beckert, R.; Fehling, P.; Doring, M.; Brandenburg, J.; Gorls, H.; Langer, P. J. Heterocycl. Chem. 1999, 36, 627.
51. (r) Nassar, S. A. Egypt. J. Chem. 2004, 47, 435.
52. (s) Madkour, H. M. F. Heterocycl. Commun. 2002, 8, 501.
53. (t) Butter, R. N.; McKenna, E. C.; McMahon, J. M.; Daly, K. M.; Cunningham, D.; McArdle, P. J. Chem. Soc., Perkin Trans. 1 1997, 2919.
54. (u) Butter, R. N.; Daly, K. M.; McMahon, J. M.; Burke, R. A. J. Chem. Soc., Perkin Trans. 1 1997, 2919.
55. (v) Kliegel, W.; Frackenstein, G. H. Justus Liebigs Ann. Chem. 1977, 956.
56. (w) Ullmann, E. F.; Coll, L.; Tseng, S. S. J. Am. Chem. Soc. 1973, 95, 1677.
57. (a) Agirbas, H.; Dueruest, Y.; Karahasanoglu, A. Phosphorus, Sulfur Silicon Relat. Elem. 1996, 114, 173.
58. (b) Evenson, G. N.; Moffett, R. B. J. Heterocycl. Chem. 1980, 351.
59. (c) Gnichtel, H.; Thiele, S. Chem. Ber. 1971, 104, 1507.
60. (d) Geffken, D.; Zydowitz, H.; Ploetz, A. Z. Naturforsch., B 2005, 60, 967.
61. (e) Zinner, G.; Schmidt, J.; Kilnig, W. Arch. Pharm. (Weinheim, Ger.) 1980, 313, 35.
62. (f) Nakanishi, S.; Nantaku, J.; Otsuji, Y. Chem. Lett. 1983, 341.
63. (g) Gouverneur, V.; Ghosez, L. Tetrahedron 1996, 52, 7585.
64. For recent examples, see: (a) Alonso, F.; Radivoy, G.; Yus, M. Russ. Chem. Bull. 2003, 52, 2563; and references cited therein.
65. (b) Alonso, F.; Radivoy, G.; Yus, M. Synthesis 2001, 427.
66. (c) Chewier, C.; LeNouen, D.; Neuburger, M.; Defoin, A.; Tarnus, C. Tetrahedron Lett. 2004, 45, 5363.
67. (a) Ostrowska, K.; Kolasa, A. In Science of Synthesis, Vol. 22; Padwa, A., Ed.; Thieme: Stuttgart, 2004, 379.
68. (b) Langer, P.; Schroeder, R. Eur. J. Org. Chem. 2004, 1025.
69. (c) Yoshimura, J. Bull. Chem. Soc. Jpn. 1971, 44, 3131.
70. (d) Lozinskii, M. O.; Shivanyuk, A. F.; Pel'kis, P. S. Chem. Heterocycl. Compd. (Engl. Transl.) 1971, 7, 439.
71. (e) Ginsburg, V. A.; Vasil'eva, M. N. J. Gen. Chem. USSR (Engl. Transl.) 1967, 37, 2371.
72. (f) Kroehnke, F.; Steuernagel, H. H. Chem. Ber. 1963, 96, 486.
73. (g) Lander, G. D. J. Chem. Soc. 1907, 91, 967.
74. (h) Lander, G. D. J. Chem. Soc. 1904, 85, 995.
75. (i) Lander, G. D. J. Chem. Soc. 1902, 81, 593.
76. (j) Anschuetz, R.; Stiepel, J. Justus Liebigs Ann. Chem. 1899, 306, 14.
77. (k) Klinger, H. Justus Liebigs Ann. Chem. 1877, 184, 280.
78. (l) Klinger, H. Chem. Ber. 1875, 8, 312.
79. (a) Mason, J. C.; Tennant, G. J. Chem. Soc., Chem. Commun. 1972, 218.
80. (b) El-Sharief, A. M. Sh.; Ammar, Y. A.; Mohamed, Y. A.; El-Gaby, M. S. A. Phosphorus, Sulfur Silicon Relat. Elem. 1999, 148, 215.
81. (c) Ahmad, Y.; Habib, M. S.; Iqbal, M.; Ziauddin, . Bull. Chem. Soc. Jpn. 1965, 38, 562.
82. (d) Dudash, J.; Zhang, Y.; Moore, J. B.; Look, R.; Liang, Y.; Beavers, M. P.; Conway, B. R.; Rybczynski, P. J.; Demarest, K. T. Bioorg. Med. Chem. Lett. 2005, 15, 4790.
83. (a) Sako, S. Mem. Coll. Eng. Kyushu Imp. Univ. 1932, 6, 263.
84. (b) Insole, J. M. J. Chem. Soc. C 1971, 1712.
85. (c) Scherz, M. W.; Fialeix, M.; Fischer, J. B.; Laxma Reddy, N.; Server, A. C.; Sonders, M. S.; Tester, B. C.; Weber, E.; Wong, S. T.; Keana, J. F. W. J. Med. Chem. 1990, 33, 2421.
86. (d) Ried, W.; Sinharay, A. Chem. Ber. 1965, 98, 3523.
87. (e) Ried, W.; Sinharay, A. Chem. Ber. 1964, 97, 1214.
88. (f) Fairfull, A. E. S.; Peak, D. A.; Short, W. F.; Watkins, T. I. J. Chem. Soc. 1952, 4700.
89. (g) Matsuda, K.; Yanagisawa, I.; Isomura, Y.; Mase, T.; Shibanuma, T. Synth. Commun. 1997, 27, 2393.
90. (h) Herr, R. J. In Science of Synthesis, Vol. 17; Weinreb, S. M., Ed.; Thieme: Stuttgart, 2003.
91. (a) de Aguiar, A. Ber. Dtsch. Chem. Ges. 1874, 7, 309.
92. (b) Jung, I. G.; Son, S. U.; Park, K. H.; Chung, K.-C. h.; Lee, J. W.; Chung, Y. K. Organometallics 2003, 22, 4715.
93. (c) Meric, A.; Incesu, Z.; Isikdag, I. Farmaco 2002, 57, 543.
94. (d) Isikdag, I.; Meric, A.; Gyenes, S.; Incesu, Z. Boll. Chim. Farm. 2004, 143, 110;
95. Chem. Abstr. 2005, 142, 176767.
96. (e) Maquestiau, A.; Berte, L.; Mayence, A.; Eynde, J.-J. V. Synth. Commun. 1991, 21, 2171.
97. (f) Yavari, I.; Adib, M.; Jahani-Moghaddam, F.; Bijanzadeh, H. R. Tetrahedron 2002, 58, 6901.
98. (g) Aly, A. A.; El-Shaieb, K. M. Tetrahedron 2004, 60, 3797.
99. (h) Sachs, F. Justus Liebigs Ann. Chem. 1909, 365, 162.
100. (i) King, H.; Wright, E. V. J. Chem. Soc. 1939, 253.
101. (j) Bazinet, P.; Yap, G. P. A.; Richeson, D. S. J. Am. Chem. Soc. 2003, 125, 13314.
102. (k) Maloshitskaya, O.; Sinkkonen, J.; Ovcharenko, V. V.; Zelenin, K. N.; Pihlaya, K. Tetrahedron 2004, 60, 6913.
103. (l) Davis, R.; Tamaoki, N. Org. Lett. 2005, 7, 1461.
104. (m) Borovlev, I. V.; Demidov, O. P.; Aksenov, A. V.; Pozharskii, A. F. Russ. J. Org. Chem 2004, 40, 895.
105. (a) Maitraie, D.; Yakaiah, T.; Srinivas, K.; Reddy, G. V.; Ravikanth, S.; Narsaiah, B.; Rao, P. S.; Ravikumar, K.; Sridhar, B. J. Fluorine Chem. 2006, 127, 351.
106. (b) Kidwai, M.; Saxena, S.; Khan, M. K. R.; Thukral, S. S. Eur. J. Med. Chem. 2005, 40, 816.
107. (c) Bathini, Y.; Sidhu, I.; Singh, R.; Micetish, R. G.; Toogood, P. L. Tetrahedron Lett. 2002, 43, 3295.
108. (d) Seijas, J. A.; Vázquez-Tato, M. P.; Martínez, M. M. Tetrahedron Lett. 2000, 41, 2215.
109. (e) Preet, M.; Bedi, S.; Kumar, V.; Mahajan, M. P. Bioorg. Med. Chem. Lett. 2004, 14, 5211.
110. (f) Kumar, V.; Mohan, C.; Gupta, M.; Mahajan, M. P. Tetrahedron 2005, 61, 3533.
111. Hodorowicz, M.; Stadnicka, K.; Trzewik, B.; Zaleska, B. Acta Crystallogr., Sect. E 2007, 63, o4115.
112. (a) COLLECT, Nonius B. V.: Delft: The Netherlands, 2000
113. (b) Otwinowski, Z.; Minor, W. In Methods in Enzymology, Vol. 276, Part A; Carter, C. W. Jr.; Sweet, R. M., Eds.; Academic Press: New York, 1997, 307.
114. (c) Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.; Burla, M. C.; Polidori, G.; Camalli, M. J. Appl. Crystallogr. 1994, 27, 435.
115. (d) Sheldrick, G. M. Acta Crystallogr., Sect. A 1997, 64, 112.
116. Fletcher, D. A.; Gowenlock, B. G.; Orrell, K. G. J. Chem. Soc., Perkin Trans. 2 1997, 2201.
117. Shur, M.; Israelstam, S. S. J. Org. Chem. 1968, 33, 3015.
118. Details of the X-ray crystal structure analysis for compounds 6a and 8a have been deposited in the Cambridge Crystallographic Data Centre, CCDC Nos. 683408 and 644908, respectively. Copies of this information may be obtained free of charge from The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(1223)336033; e-mail: deposit@ccdc.cam.ac.uk].