On the rearrangement of some Z-arylhydrazones of 3-benzoyl-5-phenylisoxazoles into 2-aryl-4-phenacyl-2H-1,2,3-triazoles: a kinetic study of the substituent effects in Boulton-Katritzky reactions

Tetrahedron

Volumn 71, Issue 39, 2015, Pages 7315-7322

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

^a UNIVERSITY OF PALERMO   (Italy)

^b UNIVERSITY OF BOLOGNA   (Italy)

^c UNIVERSITY OF MODENA AND REGGIO EMILIA   (Italy)

Author keywords

Boulton Katritzky reactions; Effect of substituents; Free energy relationships; Isoxazoles; Ring into ring conversion; Triazoles

Indexed keywords

1,2,3 TRIAZOLE DERIVATIVE; 1,2,4 OXADIAZOLE DERIVATIVE; 2 [2 (3 BROMOPHENYL) 5 PHENYL 2H 1,2,3 TRIAZOL 4 YL] 1 PHENYLETHANONE; 2 [2 (3 CHLOROPHENYL) 5 PHENYL 2H 1,2,3 TRIAZOL 4 YL] 1 PHENYLETHANONE; 2 [2 (3 METHYLPHENYL) 5 PHENYL 2H 1,2,3 TRIAZOL 4 YL] 1 PHENYLETHANONE; 2 [2 (3 NITROPHENYL) 5 PHENYL 2H 1,2,3 TRIAZOL 4 YL] 1 PHENYLETHANONE; 2 [2 (4 BROMOPHENYL) 5 PHENYL 2H 1,2,3 TRIAZOL 4 YL] 1 PHENYLETHANONE; 2 [2 (4 CHLOROPHENYL) 5 PHENYL 2H 1,2,3 TRIAZOL 4 YL] 1 PHENYLETHANONE; 2 [2 (4 CYANOPHENYL) 5 PHENYL 2H 1,2,3 TRIAZOL 4 YL] 1 PHENYLETHANONE; 2 [2 (4 METHYLPHENYL) 5 PHENYL 2H 1,2,3 TRIAZOL 4 YL] 1 PHENYLETHANONE; 3 BENZOYL 5 PHENYLISOXAZOLE DERIVATIVE; 3 BROMOPHENYLHYDRAZONE; 3 CHLOROPHENYLHYDRAZONE; 3 METHYLHYDRAZONE; 3 NITROPHENYLHYDRAZONE; 4 BROMOPHENYLHYDRAZONE; 4 CHLOROPHENYLHYDRAZONE; 4 CYANOPHENYLHYDRAZONE; 4 METHYLHYDRAZONE; DIOXANE; HYDRAZONE DERIVATIVE; ISOXAZOLE DERIVATIVE; PROTON; UNCLASSIFIED DRUG; WATER;

ARTICLE; BOULTON KATRITZKY REACTION; CHEMICAL REACTION; ELECTRON; ENERGY; PRIORITY JOURNAL; REACTION ANALYSIS; TEMPERATURE SENSITIVITY;

EID: 84939257575     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2015.04.007     Document Type: Article

References (42)

1. G.N. Burkhardt Nature 136 1935 684
2. G.N. Burkhardt, W.G. Kenneth Ford, and E. Singleton J. Chem. Soc. 1936 17 25
3. G.N. Burkhardt, A.G. Evans, and E. Warhurst J. Chem. Soc. 1936 25 26
4. L.P. Hammett Chem. Rev. 17 1935 125 136 Hammett, L. P. J. Am. Chem. Soc. 1937, 59, 96-103
5. L.P. Hammett Physical Organic Chemistry 1940 McGraw-Hill New York 184 228
6. L.P. Hammett Physical Organic Chemistry 2nd ed. 1970 McGraw-Hill London Chapter 10
7. O. Exner N.B. Chapman, J. Shorter, Advances in Linear Free Energy Relationships 1972 Plenum Press New York 1 69
8. O. Exner Correlation Analysis of Chemical Data 1988 Plenum Press New York, London; NY, UK
9. A. Williams Concerted Organic and Bioorganic Mechanisms 2000 CRC Press Boca Bato, FL
10. F.A. Carey, and R.J. Sundberg Advanced Organic Chemistry 2000 Kluwer Academic/Plenum New York, NY Chapter 4.8
11. A. Williams Free Energy Relationships in Organic and Bio-organic Chemistry 2003 RSC Cambridge, UK
12. See Ref. 2c, pp. 27-45.
13. D. Spinelli, G. Consiglio, C. Dell'Erba, and M. Novi S. Gronowitz, The Chemistry of Heterocyclic Compounds. Thiophene and its Derivatives 1991 J. Wiley & Sons New York, NY 295 396 part IV
14. G. Consiglio, V. Frenna, S. Guernelli, G. Macaluso, and D. Spinelli J. Chem. Soc., Perkin Trans. 2 2002 971 975 and references therein
15. D. Spinelli, A. Guareschi, and C. Dell'Erba J. Heterocycl. Chem. 4 1967 438 440
16. D. Spinelli, G. Consiglio, and R. Noto J. Chem. Soc., Perkin Trans. 2 1976 747 751 Spinelli, D.; Lamartina, L.; Noto, R.; Consiglio, G.; Chimichi, S. J. Chem. Res. 1993, (S), 300-301, (M) 1873-1890, and references therein
17. D. Spinelli, G. Guanti, and C. Dell'Erba Ric. Sci. (Rome) 38 1968 1048 1053
18. A.J. Boulton, A.R. Katritzky, and A. Hamid J. Chem. Soc. 1967 2005 2007
19. A.J. Boulton Lectures in Heterocyclic Chemistry Vols. 1 and 2 1973 Academic Press London, UK
20. M. Ruccia, N. Vivona, and D. Spinelli Adv. Heterocycl. Chem. 29 1981 141 169
21. N. Vivona, S. Buscemi, V. Frenna, and G. Cusmano Adv. Heterocycl. Chem. 56 1993 49 154
22. D. Spinelli, A. Corrao, V. Frenna, N. Vivona, and M. Ruccia J. Heterocycl. Chem. 13 1976 357 360
23. D. Spinelli, V. Frenna, A. Corrao, and N. Vivona J. Chem. Soc., Perkin Trans. 2 1978 19 22
24. Frenna, V.; Vivona, N.; Corrao, A.; Consiglio, G.; Spinelli, D. J. Chem. Res. 1981, (S), 308-309, (M), 3550-3578
25. V. Frenna, N. Vivona, G. Consiglio, A. Corrao, and D. Spinelli J. Chem. Soc., Perkin Trans. 2 1978 1325 1328
26. B. Cosimelli, V. Frenna, S. Guernelli, C.Z. Lanza, G. Macaluso, G. Petrillo, and D. Spinelli J. Org. Chem. 67 2002 8010 8018
27. F. D'Anna, V. Frenna, G. Macaluso, S. Morganti, P. Nitti, V. Pace, D. Spinelli, and R. Spisani J. Org. Chem. 69 2004 8718 8722
28. S. Marullo, S. Morganti, V. Pace, D. Spinelli, R. Spisani, and C. Tavani J. Org. Chem. 71 2006 5616 5624
29. F. D'Anna, V. Frenna, C.Z. Lanza, G. Macaluso, S. Marullo, D. Spinelli, R. Spisani, and G. Petrillo Tetrahedron 66 2010 5442 5450
30. F. D'Anna, V. Frenna, F. Ghelfi, S. Marullo, and D. Spinelli J. Org. Chem. 76 2011 2672 2678
31. V. Frenna, A. Palombo-Piccionello, B. Cosimelli, F. Ghelfi, and D. Spinelli Eur. J. Org. Chem. 2014 7006 7014 and references therein
32. V. Frenna, N. Vivona, D. Spinelli, and G. Consiglio J. Chem. Soc., Perkin Trans. 2 1987 537 540
33. C.W. Bird Tetrahedron 41 1985 1409 1414 Bird, C. W. Tetrahedron 1992, 48, 335-340
34. T. Sasaki, T. Yoshioka, and Y. Suzuki Bull. Chem. Soc. Jpn. 44 1971 185 189
35. rd edn., pp 716, 755
36. K. J. Laidler in Chemical Kinetics, MsGraw-Hill: London, 1965, pp 450-463
37. See Ref. 2c, pp 12-17 O. Schreck J. Chem. Educ. 48 1971 103 107
38. Y. Tsuno, T. Ibata, and Y. Yukawa Bull. Chem. Soc. Jpn. 32 1959 960 965 Yukawa, Y.; Tsuno, Y. Bull. Chem. Soc. Jpn. 1959, 32, 965-971; Yukawa, Y.; Tsuno, Y. Bull. Chem. Soc. Jpn. 1959, 32, 971-981; Yukawa, Y.; Tsuno, Y.; Sawada, M. Bull. Chem. Soc. Jpn. 1966, 39, 2274-2286
39. L.M. Stock, and H.C. Brown Adv. Phys. Org. Chem. 1 1963 35 154 Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165-195
40. A. Bottoni, V. Frenna, C.Z. Lanza, G. Macaluso, and D. Spinelli J. Phys. Chem. A 108 2004 1731 1740
41. N. Vivona, G. Macaluso, V. Frenna, and M. Ruccia J. Heterocycl. Chem. 20 1983 931 934
42. A. Weissberger 2nd ed. Techniques of Organic Chemistry Vol. 7 1963 Interscience New York, NY