A quantitative study of substituent effects on oxidative cyclization of some 2-aryl-substituted aldehyde thiosemicarbazones induced by ferric chloride and cupric perchlorate

Journal of Heterocyclic Chemistry

Volumn 36, Issue 3, 1999, Pages 667-674

  Noto, Renato ^a   Lo Meo, Paolo ^a   Gruttadauria, Michelangelo ^a   Werber, Giuseppe ^a  

^a UNIVERSITY OF PALERMO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER DERIVATIVE; FERRIC CHLORIDE; PERCHLORATE; THIOSEMICARBAZONE DERIVATIVE;

ARTICLE; CYCLIZATION; OXIDATION; REACTION ANALYSIS;

EID: 0032779453     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570360315     Document Type: Article

References (22)

1. R. Noto, F. Buccheri, G. Cusmano, M. Gruttadauria and G. Werber, J. Heterocyclic Chem., 28, 1421 (1991).
2. M. Gruttadauria, F. Buccheri, G. Cusmano, P. Lo Meo, R. Note and G. Werber, J. Heterocyclic Chem., 30, 765 (1993).
3. R. Noto, M. Gruttadauria, P. Lo Meo, V. Frenna and G. Werber, J. Heterocyclic Chem., 32, 1277 (1995).
4. R. Noto, M. Gruttadauria, P. Lo Meo and G. Werber, J. Heterocyclic Chem., 33, 863 (1996).
5. M. Gruttadauria, P. Lo Meo, R. Noto and G. Werber, Gazz. Chim. Ital. 127, 277 (1997).
6. D. Limal, V. Grand, R. Vanderesse, M. Marraud and A. Aubry, Tetrahedron Letters, 35, 3711 (1995).
7. D. X. West, A. E. Liberta, S. B. Padhye, R. C. Chikate, P. B. Sonawane, A. S. Kumbhar and R. G. Yerande, Coord. Chem. Rev., 123, 49 (1993).
8. O. E. Offiong and S. Martelli, Farmaco, 48, 777 (1993).
9. D. T. Connor, C. R. Kolstan, M. D. Mullican, M. W. Wilson, D. L. Flynn, G. P. Shrum and P. C. Unangst, European Patent. Appl. EP 371483 (1990); Chem. Abstr., 113, 231381t (1990); T. Murai, K. Kuriyiama, Y. Hyama, R. Nagatahira and K. Ito, Japan, Kokai Tokkyo Koho JP 02 15,069 [90,15,069] (1990); Chem. Abstr., 113, 23929a (1990); Y. Nomoto, H. Takai, T. Ono and K. Kubo, Japan, Kokai Tokkyo Koho JP 02,167,277 [90,167,277] (1990); Chem. Abstr., 113, 212010e (1990); L. I. Kruse and J. A. Finkelstein, European Patent Appl. EP 395,505 (1990); Chem. Abstr., 113,115311w (1990).
10. D. T. Connor, C. R. Kolstan, M. D. Mullican, M. W. Wilson, D. L. Flynn, G. P. Shrum and P. C. Unangst, European Patent. Appl. EP 371483 (1990); Chem. Abstr., 113, 231381t (1990); T. Murai, K. Kuriyiama, Y. Hyama, R. Nagatahira and K. Ito, Japan, Kokai Tokkyo Koho JP 02 15,069 [90,15,069] (1990); Chem. Abstr., 113, 23929a (1990); Y. Nomoto, H. Takai, T. Ono and K. Kubo, Japan, Kokai Tokkyo Koho JP 02,167,277 [90,167,277] (1990); Chem. Abstr., 113, 212010e (1990); L. I. Kruse and J. A. Finkelstein, European Patent Appl. EP 395,505 (1990); Chem. Abstr., 113,115311w (1990).
11. D. T. Connor, C. R. Kolstan, M. D. Mullican, M. W. Wilson, D. L. Flynn, G. P. Shrum and P. C. Unangst, European Patent. Appl. EP 371483 (1990); Chem. Abstr., 113, 231381t (1990); T. Murai, K. Kuriyiama, Y. Hyama, R. Nagatahira and K. Ito, Japan, Kokai Tokkyo Koho JP 02 15,069 [90,15,069] (1990); Chem. Abstr., 113, 23929a (1990); Y. Nomoto, H. Takai, T. Ono and K. Kubo, Japan, Kokai Tokkyo Koho JP 02,167,277 [90,167,277] (1990); Chem. Abstr., 113, 212010e (1990); L. I. Kruse and J. A. Finkelstein, European Patent Appl. EP 395,505 (1990); Chem. Abstr., 113,115311w (1990).
12. D. T. Connor, C. R. Kolstan, M. D. Mullican, M. W. Wilson, D. L. Flynn, G. P. Shrum and P. C. Unangst, European Patent. Appl. EP 371483 (1990); Chem. Abstr., 113, 231381t (1990); T. Murai, K. Kuriyiama, Y. Hyama, R. Nagatahira and K. Ito, Japan, Kokai Tokkyo Koho JP 02 15,069 [90,15,069] (1990); Chem. Abstr., 113, 23929a (1990); Y. Nomoto, H. Takai, T. Ono and K. Kubo, Japan, Kokai Tokkyo Koho JP 02,167,277 [90,167,277] (1990); Chem. Abstr., 113, 212010e (1990); L. I. Kruse and J. A. Finkelstein, European Patent Appl. EP 395,505 (1990); Chem. Abstr., 113,115311w (1990).
13. K. R. Reddy, K. Mogilaiah, B. Swamy and B. Sreenisvasulu, Acta Chim. Hung., 127, 45 (1990); G. Theodoridis, U.S. Patent 4,906,284 (1990); Chem. Abstr., 113, 23931v (1990).
14. K. R. Reddy, K. Mogilaiah, B. Swamy and B. Sreenisvasulu, Acta Chim. Hung., 127, 45 (1990); G. Theodoridis, U.S. Patent 4,906,284 (1990); Chem. Abstr., 113, 23931v (1990).
15. M. J. Harrison, R. O. C. Norman and W. A. F. Gladstone, J. Chem. Soc. (C), 735 (1967).
16. T. A. F. O'Mahony, R. N. Butler and F. L. Scott, J. Chem. Soc. Perkin Trans. 2, 1319 (1972).
17. M. J. M. Campbell, Coord. Chem. Rev., 15, 279 (1975); S. B. Padhye and G. B. Kauffmann, Coord. Chem. Rev., 63, 127 (1985).
18. M. J. M. Campbell, Coord. Chem. Rev., 15, 279 (1975); S. B. Padhye and G. B. Kauffmann, Coord. Chem. Rev., 63, 127 (1985).
19. Protic acids are able to catalyze such a closure: K. N. Zelenin, O. B. Kuznetsova and V. V. Alekseev, Chem. Heterocycl. Compd. (Engl. Transl.), 28, 340 and 1211 (1992); K. N. Zelenin, O. B. Kuznetsova, V. V. Alekseyev, P. B. Terentyev, V. N. Torocheshnikov and V. V. Ovcharenko, Tetrahedron, 49, 1257 (1993); K. N. Zelenin, V. V. Alekseyev, O. B. Kuznetsova, V. N. Torocheshnikov and L. A. Khorseeva, Tetrahedron, 49, 5327 (1993).
20. Protic acids are able to catalyze such a closure: K. N. Zelenin, O. B. Kuznetsova and V. V. Alekseev, Chem. Heterocycl. Compd. (Engl. Transl.), 28, 340 and 1211 (1992); K. N. Zelenin, O. B. Kuznetsova, V. V. Alekseyev, P. B. Terentyev, V. N. Torocheshnikov and V. V. Ovcharenko, Tetrahedron, 49, 1257 (1993); K. N. Zelenin, V. V. Alekseyev, O. B. Kuznetsova, V. N. Torocheshnikov and L. A. Khorseeva, Tetrahedron, 49, 5327 (1993).
21. Protic acids are able to catalyze such a closure: K. N. Zelenin, O. B. Kuznetsova and V. V. Alekseev, Chem. Heterocycl. Compd. (Engl. Transl.), 28, 340 and 1211 (1992); K. N. Zelenin, O. B. Kuznetsova, V. V. Alekseyev, P. B. Terentyev, V. N. Torocheshnikov and V. V. Ovcharenko, Tetrahedron, 49, 1257 (1993); K. N. Zelenin, V. V. Alekseyev, O. B. Kuznetsova, V. N. Torocheshnikov and L. A. Khorseeva, Tetrahedron, 49, 5327 (1993).
22. M. Busch and H. Holzmann, Chem. Ber., 34 320 (1901).