The Boulton-Katritzky reaction: A kinetic study of the effect of 5-nitrogen substituents on the rearrangement of some (Z)-phenylhydrazones of 3-benzoyl-1,2,4-oxadiazoles

European Journal of Organic Chemistry

Volumn 2014, Issue 31, 2014, Pages 7006-7014

  Frenna, Vincenzo ^a   Piccionello, Antonio Palumbo ^a   Cosimelli, Barbara ^b   Ghelfi, Franco ^c   Spinelli, Domenico ^d  

^a UNIVERSITY OF PALERMO   (Italy)

^b UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^c UNIVERSITY OF MODENA AND REGGIO EMILIA   (Italy)

^d UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Heterocycles; Hydrazones; Isomerization; Kinetics; Rearrangement

Indexed keywords

EID: 84941044683     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201402569     Document Type: Article

References (111)

1. a) A. F. Pozharskii, A. R. Katritzky, A. T. Soldatenkov, in: Heterocycles in Life and Society: An Introduction to Heterocyclic Chemistry, Biochemistry and Applications, J. Wiley-VCH, Weinheim, Germany, 2011;
2. b) T. Eicher, S. Hauptmann, A. Speicher, in: The Chemistry of Heterocycles (Structure, Reactions, Syntheses, and Applications), Wiley-VCH, Weinheim, Germany, 2012.
3. a) D. Spinelli, G. Consiglio, C. Dell'Erba, M. Novi, in: The chemistry of heterocyclic compounds. Thiophene and its derivatives (Ed.: S. Gronowitz), John Wiley & Sons, New York, 1991, part IV, p. 295-396;
4. b) G. Consiglio, D. Spinelli, C. Dell'Erba, M. Novi, G. Petrillo, Gazz. Chim. Ital. 1997, 127, 753-769;
5. c) L. Bianchi, C. Dell'Erba, M. Maccagno, S. Morganti, G. Petrillo, E. Rizzato, F. Sancassan, E. Severi, D. Spinelli, C. Tavani, ARKIVOC (Gainesville, FL, U.S.) 2006, 169-185;
6. d) L. Bianchi, M. Maccagno, G. Petrillo, D. Spinelli, M. Stenta, C. Tavani, Targets in Heterocyclic Systems: Chemistry and Properties, Italian Chemical Society, Rome, 2006, 10, 1-23;
7. e) L. Bianchi, M. Maccagno, G. Petrillo, E. Rizzato, D. Spinelli, C. Tavani, M. Viale, Targets in Heterocyclic Systems: Chemistry and Properties, Italian Chemical Society, Rome, 2007, 11, 1-20;
8. f) F. D'Anna, V. Frenna, R. Noto, V. Pace, D. Spinelli, J. Org. Chem. 2006, 71, 5144-5150;
9. g) C. Dell'Erba, D. Spinelli, G. Leandri, J. Chem. Soc. C 1969, 549-549;
10. h) F. Guerrera, L. Salerno, L. Lamartina, D. Spinelli, J. Chem. Soc. Perkin Trans. 1 1995, 1243-1246;
11. i) D. Spinelli, P. Zanirato, E. De Miceli, L. Lamartina, F. Guerrera, J. Org. Chem. 1997, 62, 4921-4923;
12. j) B. Cosimelli, L. Lamartina, D. Spinelli, Tetrahedron 2001, 57, 8903-8911;
13. k) B. Cosimelli, L. Lamartina, C. Z. Lanza, D. Spinelli, R. Spisani, F. Vegna, Tetrahedron 2003, 59, 7189-7201;
14. l) G. Consiglio, V. Frenna, S. Guernelli, G. Macaluso, D. Spinelli, J. Chem. Soc. Perkin Trans. 2 2002, 971-975;
15. m) L. Bianchi, M. Maccagno, G. Petrillo, F. Sancassan, C. Tavani, S. Morganti, E. Rizzato, D. Spinelli, J. Org. Chem. 2007, 72, 5771-5777.
16. a) D. Spinelli, Ph.D. Thesis, University of Bari, 1955;
17. b) S. Cusmano, M. Ruccia, Gazz. Chim. Ital. 1955, 85, 1686-1697;
18. c) S. Cusmano, M. Ruccia, Gazz. Chim. Ital. 1958, 88, 463-481;
19. d) B. Cavalleri, P. Bellani, G. Lancini, J. Heterocycl. Chem. 1973, 10, 357-362.
20. a) D. Spinelli, A. Mugnoli, A. Andreani, M. Rambaldi, S. Frascari, J. Chem. Soc., Chem. Commun. 1992, 1394-1395;
21. b) A. Andreani, R. Billi, B. Cosimelli, A. Mugnoli, M. Rambaldi, D. Spinelli, J. Chem. Soc. Perkin Trans. 2 1997, 2407-2410;
22. c) R. Billi, B. Cosimelli, D. Spinelli, M. Rambaldi, Tetrahedron 1999, 55, 5433-5440;
23. d) R. Billi, B. Cosimelli, D. Spinelli, A. Andreani, A. Leoni, Tetrahedron 2000, 56, 6527-6532;
24. e) B. Cosimelli, V. Frenna, M. Rambaldi, E. Severi, D. Spinelli, Tetrahedron Lett. 2014, 55, 1488-1490;
25. f) A. Bottoni, M. Calvaresi, A. Ciogli, B. Cosimelli, G. Mazzeo, L. Pisani, E. Severi, D. Spinelli, S. Superchi, Adv. Synth. Catal. 2013, 355, 191-202.
26. V. Frenna, N. Vivona, G. Macaluso, D. Spinelli, G. Consiglio, J. Chem. Soc. Perkin Trans. 2 1987, 537-540.
27. a) M. Ruccia, N. Vivona, D. Spinelli, Adv. Heterocycl. Chem. 1981, 29, 141-169;
28. b) N. Vivona, S. Buscemi, V. Frenna, G. Cusmano, Adv. Heterocycl. Chem. 1993, 56, 49-154;
29. c) M. Ruccia, D. Spinelli, Gazz. Chim. Ital. 1959, 89, 1654-1669;
30. d) D. Spinelli, A. Corrao, V. Frenna, N. Vivona, M. Ruccia, G. Cusmano, J. Heterocycl. Chem. 1976, 13, 357-360;
31. e) V. Frenna, N. Vivona, G. Consiglio, A. Corrao, D. Spinelli, J. Chem. Soc. Perkin Trans. 2 1981, 1325-1328;
32. f) B. Cosimelli, V. Frenna, S. Guernelli, C. Z. Lanza, G. Macaluso, G. Petrillo, D. Spinelli, J. Org. Chem. 2002, 67, 8010-8018;
33. g) A. Bottoni, V. Frenna, C. Z. Lanza, G. Macaluso, D. Spinelli, J. Phys. Chem. A 2004, 108, 1731-1740;
34. h) N. Vivona, N. Ruccia, G. Cusmano, M. L. Marino, D. Spinelli, J. Heterocycl. Chem. 1975, 12, 1327-1328;
35. i) A. Mugnoli, G. Barone, S. Buscemi, C. Z. Lanza, A. Pace, M. Pani, D. Spinelli, J. Phys. Org. Chem. 2009, 22, 1086-1093;
36. j) F. D'Anna, V. Frenna, G. Macaluso, S. Marullo, S. Morganti, V. Pace, D. Spinelli, R. Spisani, C. Tavani, J. Org. Chem. 2006, 71, 5616-5624;
37. k) F. D'Anna, V. Frenna, C. Z. Lanza, G. Macaluso, S. Marullo, D. Spinelli, R. Spisani, G. Petrillo, Tetrahedron 2010, 66, 5442-5450;
38. l) M. D'Auria, V. Frenna, S. Marullo, R. Racioppi, D. Spinelli, L. Viggiani, Photochem. Photobiol. Sci. 2012, 11, 1383-1388;
39. m) S. Guernelli, R. Zappacorta, G. Siani, D. Spinelli, A. Fontana, J. Mol. Catal. A 2014, 383-384, 114-120;
40. n) A. Palumbo Piccionello, A. Pace, S. Buscemi, N. Vivona, G. Giorgi, Tetrahedron Lett. 2009, 50, 1472- 1474;
41. o) A. Pace, I. Pibiri, A. Palumbo Piccionello, S. Buscemi, N. Vivona, G. Barone, J. Org. Chem. 2007, 72, 7656-7666;
42. p) A. Palumbo Piccionello, A. Pace, S. Buscemi, N. Vivona, M. Pani, Tetrahedron 2008, 64, 4004-4010;
43. q) A. Palumbo Piccionello, A. Pace, S. Buscemi, N. Vivona, Org. Lett. 2009, 11, 4018-4020;
44. r) A. Palumbo Piccionello, S. Buscemi, N. Vivona, A. Pace, Org. Lett. 2010, 12, 3491-3493;
45. s) A. Martorana, A. Palumbo Piccionello, S. Buscemi, G. Giorgi, A. Pace, Org. Biomol. Chem. 2011, 9, 491-496
46. a) A. J. Boulton, A. R. Katrizky, A. Hamid, J. Chem. Soc. C 1967, 2005-2007;
47. b) A. J. Boulton, in: Lectures in Heterocyclic Chemistry, Academic Press, London, 1973, vol. 1 and 2.
48. a) H. C. Van der Plas, in: Ring Transformations of Heterocycles, Academic Press, London, 1973, vol. 1 and 2;
49. b) G. L'abbé, J. Heterocycl. Chem. 1984, 21, 627-638;
50. c) A. R. Katrizky, M. F. Gordev, Heterocycles 1993, 35, 483-518;
51. d) A. Pace, P. Pierro, Org. Biomol. Chem. 2009, 7, 4337-4348.
52. a) D. Alker, S. F. Campbell, P. E. Cross, R. A. Burges, A. J. Carter, D. G. Gardiner, J. Med. Chem. 1990, 33, 1805-1811;
53. b) D. Galanakis, C. A. Davis, B. D. R. Herrero, C. R. Ganellin, P. M. Dunn, D. H. Jenkinson, J. Med. Chem. 1995, 38, 595- 606;
54. c) H. Cerecetto, W. Porcal, Mini-Rev. Med. Chem. 2005, 5, 57-71;
55. d) U. Albrecht, D. Gördes, E. Schmidt, K. Thurow, M. Lalk, P. Langer, Bioorg. Med. Chem. 2005, 13, 4402-4407;
56. e) B. Alcaide, P. Almendros, C. Pardo, A. Rodríguez-Vicente, M. Pilar Ruiz, Tetrahedron 2005, 61, 7894-7906;
57. f) T. Tomašić, L. P. Mašič, Curr. Med. Chem. 2009, 16, 1596-1629;
58. g) R. A. Hughes, C. J. Moody, Angew. Chem. Int. Ed. 2007, 46, 7930- 7954;
59. Angew. Chem. 2007, 119, 8076;
60. h) M. R. Barbachyn, C. W. Ford, Angew. Chem. Int. Ed. 2003, 42, 2010-2023;
61. Angew. Chem. 2003, 115, 2056;
62. i) S. D. Kimball, D. M. Floyd, J. Das, J. T. Hunt, J. Krapcho, G. Rovnyak, K. J. Duff, V. G. Lee, R. V. Moquin, C. F. Turk, S. A. Hedberg, S. Moreland, R. J. Brittain, D. M. McMullen, D. E. Normandin, G. G. Cucinotta, J. Med. Chem. 1992, 35, 780-793;
63. j) R. Budriesi, B. Cosimelli, P. Ioan, C. Z. Lanza, D. Spinelli, A. Chiarini, J. Med. Chem. 2002, 45, 3475-3481;
64. k) P. J. Stephens, F. J. Devlin, F. Gasparrini, A. Ciogli, D. Spinelli, B. Cosimelli, J. Org. Chem. 2007, 72, 4707- 4715;
65. l) P. Ioan, A. Ciogli, F. Sirci, R. Budriesi, B. Cosimelli, E. Severi, A. Chiarini, G. Cruciani, F. Gasparrini, D. Spinelli, E. Carosati, Org. Biomol. Chem. 2012, 10, 8994-9003;
66. m) M. Viale, C. Cordazzo, B. Cosimelli, D. de Todero, P. Castagnola, C. Aiello, E. Severi, G. Petrillo, M. Cianfriglia, D. Spinelli, J. Med. Chem. 2009, 52, 259-266;
67. n) C. Rosano, M. Viale, B. Cosimelli, E. Severi, R. Gangemi, A. Ciogli, D. de Todero, D. Spinelli, ACS Med. Chem. Lett. 2013, 4, 694-698;
68. o) R. A. Coburn, M. Wierzba, M. J. Suto, A. J. Solo, A. M. Triggle, D. J. Triggle, J. Med. Chem. 1988, 31, 2103-2107;
69. p) M. S. Egbertson, Curr. Top. Med. Chem. 2007, 7, 1251-1272;
70. q) A. Castro, T. Castaño, A. Encinas, W. Porcal, C. Gil, Bioorg. Med. Chem. 2006, 14, 1644-1652;
71. r) C. V. Galliford, K. A. Scheidt, Angew. Chem. Int. Ed. 2007, 46, 8748-8758;
72. Angew. Chem. 2007, 119, 8902;
73. s) A. Terenzi, G. Barone, A. Palumbo Piccionello, G. Giorgi, A. Guarcello, P. Portanova, G. Calvaruso, S. Buscemi, N. Vivona, A. Pace, Dalton Trans. 2010, 39, 9140- 9145;
74. t) V. M. Dembitsky, T. A. Gloriozova, V. V. Poroikov, Mini-Rev. Med. Chem. 2005, 5, 319-336;
75. u) M. Malesevic, D. Gutknecht, E. Prell, C. Klein, M. Schumann, R. A. Nowak, J. C. Simon, C. Schiene-Fischer, A. Saalbach, J. Med. Chem. 2013, 56, 7302-7311;
76. v) M. G. Ferlin, D. Carta, R. Bortolozzi, R. Ghodsi, A. Chimento, V. Pezzi, N. Hanke, R. W. Hartmann, G. Basso, G. Viola, J. Med. Chem. 2013, 56, 7536-7551;
77. w) J. Y. Choi, C. M. Calvet, S. S. Gunatilleke, C. Ruiz, M. D. Cameron, J. H. McKerrow, L. M. Podust, W. R. Roush, J. Med. Chem. 2013, 56, 7651-7668;
78. x) C. G. Fortuna, C. Bonaccorso, A. Bulbarelli, G. Caltabiano, L. Rizzi, L. Goracci, G. Musumarra, A. Pace, A. Palumbo Piccionello, A. Guarcello, P. Pierro, C. E. A. Cocuzza, R. Musumeci, Eur. J. Med. Chem. 2013, 65, 533-545;
79. y) L. Lentini, R. Melfi, A. Di Leonardo, A. Spinello, G. Barone, A. Pace, A. Palumbo Piccionello, I. Pibiri, Mol. Pharm. 2014, 11, 653-664;
80. z) A. Palumbo Piccionello, G. Pitarresi, A. Pace, D. Triolo, P. Picone, S. Buscemi, G. Giammona, J. Drug Targeting 2012, 20, 433-444.
81. a) J. Velik, V. Baliharová, J. Fink-Gremmels, S. Bull, J. Lamka, L. Skálová, Res. Vet. Sci. 2004, 76, 95-108;
82. b) J. Matsumoto, Int. J. Parasitol. 2002, 32, 461-471;
83. c) M. Tapia-Salazar, T. K. Smith, A. Harris, D. Ricque-Marie, L.-E. Cruz-Suarez, Aquaculture 2001, 193, 281-289;
84. d) G. Gargala, L. Le Goff, J. J. Ballet, L. Favennec, A. V. Stachulski, J. F. Rossignol, Vet. Parasitol. 2009, 162, 230-235.
85. a) L. Mercs, M. Albrecht, Chem. Soc. Rev. 2010, 39, 1903-1912;
86. b) N. Robertson, L. Cronin, Coord. Chem. Rev. 2002, 227, 93-127;
87. c) P. K. Swain, H. Singh, S. P. Tewari, J. Mol. Liq. 2010, 151, 87-96;
88. d) A. R. Murphy, J. M. J. Frechet, Chem. Rev. 2007, 107, 1066-1096;
89. e) A. Martorana, A. Pace, S. Buscemi, A. Palumbo Piccionello, Org. Lett. 2012, 14, 3240-3243;
90. f) A. Palumbo Piccionello, A. Guarcello, A. Calabrese, I. Pibiri, A. Pace, S. Buscemi, Org. Biomol. Chem. 2012, 10, 3044-3052;
91. g) N. A. Zafiropoulos, W. Lin, E. T. Samulskii, T. J. Dingemans, S. J. Picken, Liq. Cryst. 2009, 36, 649-656;
92. h) V. Gortz, C. Southern, N. W. Roberts, H. F. Gleeson, J. W. Goodby, Soft Matter 2009, 5, 463-471;
93. i) F. Speetjens, J. Lindborg, T. Tauscher, N. LaFemina, J. Nguyen, E. T. Samulski, F. Vita, O. Francescangeli, E. Scharrer, J. Mater. Chem. 2012, 22, 22558-22564;
94. j) G. Shanker, C. Tschierske, Tetrahedron 2011, 67, 8635-8638;
95. k) H. Gallardo, M. Ferreira, A. A. Vieira, E. Westphal, F. Molin, J. Eccher, I. H. Bechtold, Tetrahedron 2011, 67, 9491-9499.
96. On the use of heterocycles as masked functionalities, see: a) A. Dondoni, in: Modern Synthetic Methods (Ed.: R. Scheffold), Verlag Helvetica Chimica Acta, Basel, 1992, p. 377-437;
97. b) The Chemistry of Functional Groups (Ed.: S. Patai, Z. Rappoport), Wiley, New York, a series of monographs edited from 1992 to today;
98. c) Chem. Rev. 2004, 104, 2125-2776; an issue (Ed.: A. R. Katrizky) dedicated to different aspects of heterocyclic chemistry.
99. a) C. W. Bird, Tetrahedron 1985, 41, 1409-1414;
100. b) C. W. Bird, Tetrahedron 1992, 48, 335-340.
101. H. S. Harned, B. B. Owen, in: The Physical Chemistry of Electrolytic Solution, A. C. S. Monograph No. 137, Reinhold, New York, 1958, 3rd ed., pp 716, 755.
102. K. J. Laidler, in: Chemical Kinetics, McGraw-Hill, London, 1965, p. 450-463.
103. C. Hansch, A. Leo, R. W. Taft, Chem. Rev. 1991, 91, 165-195.
104. a) L. P. Hammett, in: Physical Organic Chemistry, 2nd ed., McGraw-Hill, New York, 1970, chapter 10;
105. b) O. Exner, in: Correlation Analysis of Chemical Data, Plenum Press, New York and London, 1988, chapter 7.4;
106. c) A. Williams, in: Concerted Organic and Bioorganic Mechanisms, CRC Press, Boca Raton, FL, 2000;
107. d) F. A. Carey, R. J. Sundberg, in: Advanced Organic Chemistry, Kluwer Academic/Plenum Publishers, New York, 2000, chapter 4.8;
108. e) A. Williams, in: Free Energy Relationships in Organic and Bio-organic Chemistry, RSC, Cambridge, UK, 2003.
109. J. Daroszewski, B. Serafin, G. Borkowska, S. Rump, Pharmazie 1986, 41, 699-702.
110. a) P. De Maria, R. Noto, G. Consiglio, D. Spinelli, J. Chem. Soc. Perkin Trans. 2 1989, 791-795;
111. b) A. Albert, E. P. Serjeant, in: Ionization Constants of Acids and Bases, Methuen, London, 1962.