SEAr-SNAr couplings of indolizines and related pyrrole derivatives with superelectrophilic nitrobenzoxadiazoles

Tetrahedron

Volumn 66, Issue 4, 2010, Pages 995-1006

  Tatarov, Artem ^a   Kurbatov, Serguey ^a   Borodkin, Gennady ^a   Goumont, Régis ^b   Terrier, François ^b  

^a SOUTHERN FEDERAL UNIVERSITY   (Russian Federation)

^b UNIVERSITÉ DE VERSAILLES SAINT QUENTIN EN YVELINES   (France)

Author keywords

Indolizine nucleophilicity; Pyrrole nucleophilicity; SEAr SNAr couplings; Superelectrophilic nitrobenzoxadiazoles; Zwitterionic spiro adducts

Indexed keywords

7 CHLORO 4,6 DINITROBENZOFURAN; 7 CHLORO 4,6 DINITROBENZOFUROXAN; ACETONITRILE; ALKENE; AMPHOLYTE; AROMATIC CARBOXYLIC ACID; BENZOFURAN DERIVATIVE; BENZOFURAZAN DERIVATIVE; CARBON; CHLORINE; DIHYROPYRROLOISOQUINOLINE; FURAN DERIVATIVE; INDOLIZINE DERIVATIVE; ISOQUINOLINE DERIVATIVE; ISOXAZOLE DERIVATIVE; NITROBENZOXADIAZOLE; NUCLEOPHILE; OXADIAZOLE DERIVATIVE; OXIDE; OXYGEN; PYRIDINE; PYRROLE; PYRROLE DERIVATIVE; SPIROBENZOFURAZAN; UNCLASSIFIED DRUG;

ARTICLE; ATOM; CHEMICAL BOND; CHEMICAL COMPOSITION; CHEMICAL PHENOMENA; CHEMICAL REACTION; COMPLEX FORMATION; CROSS COUPLING REACTION; CROSS LINKING; CRYSTAL STRUCTURE; CYCLOADDITION; ELECTRON; ELECTRON TRANSPORT; MOLECULAR STABILITY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; ROOM TEMPERATURE; SUBSTITUTION REACTION;

EID: 72149113066     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.11.071     Document Type: Article

References (107)

1. Terrier F., Kizilian E., Halle J.C., and Buncel E. J. Am. Chem. Soc. 114 (1992) 1740
2. Terrier F., Pouet M.J., Halle J.C., Hunt S., Jones J.R., and Buncel E. J. Chem. Soc., Perkin Trans. 2 (1993) 1665
3. Buncel E., Renfrow R.A., and Strauss M.J. J. Org. Chem. 52 (1987) 488
4. Buncel E., Manderville R.A., and Dust J.M. J. Chem. Soc., Perkin Trans. 2 (1997) 1019
5. Crampton M.R., and Rabbitt L.C. J. Chem. Soc., Perkin Trans. 2 (1999) 1669
6. Crampton M.R., Rabbitt L.C., and Terrier F. Can. J. Chem. 77 (1999) 639
7. Crampton M.R., Lunn R.E.A., and Lucas D. Org. Biomol. Chem. 1 (2003) 3438
8. Asghar B.H.M., and Crampton M.R. Org. Biomol. Chem. 5 (2007) 1646
9. Asghar B.H.M., and Crampton M.R. J. Phys. Org. Chem. 20 (2007) 702
10. Asghar B.H.M., Crampton M.R., and Isanbor C. Can. J. Chem. 86 (2008) 225
11. Boga C., and Forlani L. J. Chem. Soc., Perkin Trans. 2 (2001) 1408
12. Boga C., Del Vecchio E., Forlani L., Mazzanti A., and Todesco P.E. Angew. Chem., Int. Ed. 44 (2005) 3285
13. Forlani L., Tocke A.L., Del Vecchio E., Lakhdar S., Goumont R., and Terrier F. J. Org. Chem. 71 (2006) 5527
14. Remennikov G.Y., Kempf B., Ofial A.R., Polborn K., and Mayr H. J. Phys. Org. Chem. 16 (2003) 431
15. Evgen'yev M.I., Garmonov S.Y., Shakirova L.S., and Brysaev A.S. J. Anal. Chem. 57 (2002) 1103
16. Evgen'ev M.I., Evgen'eva I.I., Levinson F.S., Ermolaeva E.A., and Valitova Y.R. J. Anal. Chem. 61 (2006) 133
17. Kurbatov S.V., Budarina Z.N., Vaslyaeva G.S., Borisenko N.I., Knyazev A.P., Minkin V.I., Zhdanov Y.A., and Olekhnovich L.P. Izv. Acad. Nauk, Ser. Khim. (1997) 1509
18. Olekhnovich L.P., Budarina Z.N., Lesin A.V., Kurbatov S.V., Borodkin G.S., and Minkin V.I. Mendeleev Commun. (1997) 162
19. Terrier F., Millot F., and Norris W.P. J. Am. Chem. Soc. 98 (1976) 5883
20. Terrier F., Chatrousse A.P., Soudais Y., and Hlaibi M. J. Org. Chem. 49 (1984) 4176
21. Lakhdar S., Goumont R., Boubaker T., Mokhtari M., and Terrier F. Org. Biomol. Chem. 4 (2006) 1910
22. Bernasconi C.F. J. Am. Chem. Soc. 93 (1972) 6975
23. Crampton M.R. Adv. Phys. Org. Chem. 7 (1969) 211
24. Strauss M.J. Chem. Rev. 70 (1970) 667
25. Terrier F. Chem. Rev. 82 (1982) 77
26. Buncel E. In: Patai S. (Ed). The Chemistry of Amino, Nitro and Nitroso Compounds (1982), Wiley, London
27. Buncel E., Crampton M.R., Strauss M.J., and Terrier F. Electron-Deficient Aromatic- and Heteroaromatic-Base Interactions (1984), Elsevier, Amsterdam
28. Part 2. Paradisi C. In: Trost B.M. (Ed). Comprehensive Organic Synthesis Vol. 4 (1991), Pergamon, Oxford
29. Terrier F. In: Feuer H. (Ed). Nucleophilic Aromatic Displacement (1991), VCH, New York, NY
30. Terrier F., Pouet M.J., Halle J.C., Kizilian E., and Buncel E. J. Phys. Org. Chem. 11 (1998) 707
31. Read R.W., Spear R.J., and Norris W.P. Aust. J. Chem. 36 (1983) 1227
32. Read R.W., and Norris W.P. Aust. J. Chem. 38 (1985) 297
33. Kizilian E., Terrier F., Chatrousse A.P., Gzouli K., and Halle J.C. J. Chem. Soc., Perkin Trans. 2 (1997) 2667
34. Terrier F., Halle J.C., Simonnin M.P., and Pouet M.J. J. Org. Chem. 49 (1984) 4363
35. Lakhdar S., Westermaier M., Terrier F., Goumont R., Boubaker T., Ofial A.R., and Mayr H. J. Org. Chem. 71 (2006) 9088
36. Terrier F., Lakhdar S., Boubaker T., and Goumont R. J. Org. Chem. 70 (2005) 6242
37. Moutiers G., Goumont R., Pinson J., and Terrier F. Chem.-Eur. J. 7 (2001) 1712
38. Goumont R., Jan E., Makosza M., and Terrier F. Org. Biomol. Chem. 1 (2003) 2192
39. Sikder M.A.K., Salunke R.B., and Sikder N. New J. Chem. 25 (2001) 1549
40. Bemi M., Vasilescu M., Caproiu M.T., Draghici C., Beteringhe A., Constantinescu T., Banciu M.D., and Balaban A.T. Cent. Eur. J. Chem. (2004) 672
41. Kurbatov S., Rodriguez Da Fonte P., Goumont R., Marrot J., and Terrier F. Chem. Commun. (2003) 2150
42. Vogel S., Kmoche W., and Schoeller W.W. J. Chem. Soc., Perkin Trans. 2 (1986) 769
43. Effenberger F. Acc. Chem. Res. 22 (1989) 27
44. Effenberger F., Agster W., Fischer P., Jogun K.H., Stezowski J.J., Daltrozzo E., and Kohlmannsberger-von Nell G.J. Org. Chem. 48 (1983) 4649
45. Shipman M. In: Thomas J. (Ed). Science of Synthesis Vol. 10 (2000), Georg Thieme, Stuttgart, New York, NY 745-787
46. Fraser M., McKenzie S., and Reid D.H. J. Chem. Soc. B (1966) 44
47. Armarego W.L.F. J. Chem. Soc. (1964) 4226
48. Tietzer L.F., and Eicher T. Reaktionen und Synthesen im organisch-chemischen: Praktikum und Forschungslaboratorium (1991), Georg Thieme, Stuttgart, New York, NY pp 359-360
49. Terrier F., Debleds F.L., Verchere J.F., and Chatrousse A.P. J. Am. Chem. Soc. 107 (1985) 307
50. Jones R.A., and Bean G.P. The Chemistry of Pyrroles (1977), Academic, London, New York, NY pp 446-451
51. Kurbatov S.V., Tatarov A.V., Minkin V.I., Goumont R., and Terrier F. Chem. Commun. (2006) 4279
52. Lowe-Ma C.K., Nissan R.A., and Wilson S. J. Org. Chem. 55 (1990) 3755
53. Terrier F., Halle J.C., MacCormack P., and Pouet M.J. Can. J. Chem. 67 (1989) 503
54. Cmoch P., Stefaniak L., and Webb G.A. Magn. Reson. Chem. 35 (1997) 483
55. Anet F.A.L., and Yavari I. Org. Magn. Reson. 8 (1976) 158
56. Witanowski M., Stefaniak L., Biernat S., and Webb G.A. Org. Magn. Reson. 14 (1980) 356
57. Katritzky A.R., and Gordeev M.F. Heterocycles 35 (1993) 483
58. Wennerström H., and Wennerström O. Acta Chem. Scand. 96 (1972) 2883
59. Hosoya H., Hosoya S., and Nagakura S. Theor. Chim. Acta 12 (1968) 117
60. Strauss M.J., Fleischmann S., and Buncel E. J. Mol. Struct. 121 (1985) 37
61. Olah G., and Mayr H. J. Org. Chem. 41 (1976) 3448
62. Terrier F., Millot F., Chatrousse A.P., Pouet M.J., and Simonnin M.P. Org. Magn. Reson. 8 (1976) 56
63. Terrier F., Goumont R., Pouet M.J., and Halle J.C. J. Chem. Soc., Perkin Trans. 2 (1995) 1629
64. Casagrande C., Invernizzi A., Ferrini R., and Ferrari G.G. J. Med. Chem. 11 (1968) 765
65. Shevchuk M.I., and Dombrovskii A.V. Zh. Obshch. Khim. 33 (1963) 1135
66. Pitts M.R., Harrison J.R., and Moody C.J. J. Chem. Soc., Perkin Trans. 1 (2001) 955
67. Perrin D.D. Pure Appl. Chem. 20 (1969) 133
68. Perrin D.D. Dissociation Constants of Inorganic Acids and Bases in Aqueous Solution (1969), Butterworths, London
69. Makosza M. In: Nozaki H. (Ed). Current Trends in Organic Synthesis (1993), Pergamon, New York, NY 401
70. Makosza M., and Woniarski J. Acc. Chem. Res. 20 (1987) 282
71. Makosza M., and Wojciechowski K. Chem. Rev. 104 (2004) 2631
72. Chupakhin O.N., Charushin V.N., and Van der Plas H.C. Nucleophilic Aromatic Substitution of Hydrogen (1994), Academic, San Diego, CA
73. Kozhevnikov D.N., Rusinov V.L., Chupakhin O.N., Makosza M., Rykiwski A., and Wolinska E. Eur. J. Org. Chem. (2002) 1412
74. Prokhorov A.M., Kozhevnikov D.N., Rusinov V.L., and Chupakhin O.N. Russ. Chem. Bull. Int. Ed. 52 (2003) 1195
75. Kozhevnikov D.N., Kataeva N.N., Rusinov V.L., Chupakhin O.N., and Alexandrov G.G. Mendeleev Commun. (2005) 31
76. Terrier F., Beaufour M., Halle J.C., Cherton J.C., and Buncel E. Tetrahedron Lett. 42 (2001) 4499
77. Jones R.L., and Rees C.W. J. Chem. Soc. C (1969) 2255
78. Landor S.R., Rogers V., and Sood H.R. J. Chem. Soc., Perkin Trans. 1 (1976) 2103
79. Gabbut P.D., Hepworth J.D., Heron B.M., Elsegood M.R.J., and Clegg W. Chem. Commun. (1999) 289
80. Gambarcorta A., Nicoletti R., and Forcellese M.L. Tetrahedron 27 (1971) 985
81. Elliot A.R., Herrick A.B., and Roder T.M. J. Am. Chem. Soc. 72 (1950) 2760
82. Turner P.G., Donokse T.J., and Cousins R.P.C. Chem. Commun. (2004) 1422
83. Bernasconi C.F. Acc. Chem. Res. 11 (1978) 147
84. Bernasconi C.F., and Gehriger C.L. J. Am. Chem. Soc. 96 (1974) 1092
85. Bernasconi C.F., Gehriger C.L., and De Rossi R.D. J. Am. Chem. Soc. 98 (1976) 8451
86. Bernasconi C.F., and Terrier F. J. Am. Chem. Soc. 97 (1975) 7458
87. Bernasconi C.F., and Howard K. J. Am. Chem. Soc. 104 (1982) 7248
88. Bernasconi C.F., and Gemdler J.R. J. Org. Chem. 42 (1977) 3387
89. Crampton M.R., and Willison M.J. J. Chem. Soc., Perkin Trans. 2 (1974) 1681
90. Jenks W.P. Catalysis in Chemistry and Enzymology (1969), McGraw-Hill, New York, NY Chapter 3
91. Kirby A.J., and Jenks W.P. J. Am. Chem. Soc. 87 (1965) 3217
92. Kurbatov S.V., Budarina Z.N., Vaslyaeva G.S., Borisenko N.I., Knyazev A.P., Minkin V.I., Zhdanov Y.A., and Olekhnovich L.P. Russ. Chem. Bull. Int. Ed. 46 (1997) 1445
93. Morozov P.G., Kurbatov S.V., and Olekhnovich L.P. Chem. Heterocycl. Comp. 38 (2001) 1428
94. Morozov P.G., Kurbatov S.V., Dolgushin F.M., Antipin M.Y., and Olekhnovich L.P. Russ. Chem. Bull. Int. Ed. 53 (2004) 2075
95. Voronina V.A., Kurbatov S.V., and Olekhnovich L.P. Russ. J. Org. Chem. 40 (2004) 1384
96. Terrier F., Xiao L., Hlaibi M., and Halle J.C. J. Chem. Soc., Perkin Trans. 2 (1993) 337
97. Sharnin, G. I.; Levinson, S. A.; Akimova, S. A.; Kasamov, R. K. USSR Patent 657,025, 1979.
98. Chem. Abstr. 91 (1979) P20519h
99. Norris W.P., Chafin A., Spear R.J., and Read R.W. Heterocycles 22 (1984) 271
100. Tchichibabin A.E. Ber. Dtsch. Chem. Ges. 60 (1927) 1607
101. Posseels G., Peiven M., Cornil R., Prost M., and Descamps M. Ing. Chem. (Brussels) 63 (1981) 3
102. Anitha I., and Rajan P.K. J. Indian Chem. Soc. 66 (1989) 460
103. Borrows E.T., Holland D.O., and Kenyon J. J. Chem. Soc. (1946) 1077
104. Lins C.L.K., Block J.H., and Ooerge R.F. J. Pharm. Sci. 71 (1982) 556
105. Kochetkova E.A. Zh. Obshch. Khim. 73 (1963) 1201
106. Buu-Hoï N.P., Jacquignon P., Xuong N.D., and Lavit D. J. Org. Chem. 19 (1954) 1370
107. Cliff G.R., Jones G., and Stanyer J. J. Chem. Soc. C (1971) 3426