Novel and efficient synthesis of 4-substituted-1,2,4-triazolidine-3,5- diones from anilines

Synthetic Communications

Volumn 37, Issue 11, 2007, Pages 1927-1934

  Mallakpour, Shadpour ^a   Rafiee, Zahra ^a  

^a ISFAHAN UNIVERSITY OF TECHNOLOGY   (Iran)

Author keywords

Anilines; Blocking agent; Heterocyclic compounds; Isocyanates; P nitrophenyl chloroformate; Urazole derivatives

Indexed keywords

1,2,4 TRIAZOLIDINDIONE DERIVATIVE; 4 (2 CHLORO 4 NITROPHENYL) 1,2,4 TRIAZOLIDINE 3,5 DIONE; 4 (3 NITROPHENYL) 1,2,4 TRIAZOLIDINE 3,5 DIONE; 4 (4 CHLOROPHENYL) 1,2,4 TRIAZOLIDINE 3,5 DIONE; 4 (4 METHYLPHENYL) 1,2,4 TRIAZOLIDINE 3,5 DIONE; 4 (4 NITROPHENYL) 1,2,4 TRIAZOLIDINE 3,5 DIONE; 4 BENZYL 1,2,4 TRIAZOLIDINE 3,5 DIONE; 4 PHENYL 1,2,4 TRIAZOLIDINE 3,5 DIONE; ANILINE DERIVATIVE; BENZENE DERIVATIVE; CARBAMIC ACID DERIVATIVE; FORMIC ACID DERIVATIVE; PYRROLE DERIVATIVE; SEMICARBAZIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL PROCEDURES; CHEMICAL REACTION; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; SUBSTITUTION REACTION;

EID: 34250376362     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701316862     Document Type: Article

References (37)

1. Ohashi, S.; Leong, K. W.; Matyjaszewski, K.; Butler, G. B. J. Org. Chem. 1980, 45, 3467.
2. Gilbertson, T. J.; Ryan, T. Synthesis 1982, 159.
3. Little, T.; Meara, J.; Ruan, F.; Nguyen, M.; Qabar, M. Synth. Commun. 2002, 32, 1741.
4. Park, K. H.; Cox, L. J. Tetrahedron Lett. 2002, 43, 3899.
5. Mallakpour, S. E.; Rezazadeh, S. Iranian Polym. J. 2004, 13, 29.
6. Mallakpour, S.; Rafiee, Z. Polym. Bull. 2006, 56, 293.
7. Izydore, R. A.; Hall, I. H US Patent 4,866,058, File date, Sep. 12, 1989, Chem. Abstr., 1990, 112, 151876X.
8. Wakabayashi, O.; Matsuya, K.; Ohta, H.; Jikihara, T.; Suzuki, S. Ger Offen., 2, 526, 358 Jpn., Chem. Abstr. 1976, 84, 135700h.
9. Ovadia, D.; Peleg, N.; Bracha, P. US Patent 4,087, 534, Israeli, File date, May 2, 1978, Chem. Abstr. 1978, 89, 109513h.
10. (a) Von Bredow, B.; Brechbuehler, H. Ger Offen. 2,343,347; File date, March 14, 1974, Chem. Abstr. 1974, 80, 140210s;
11. (b) Von Bredow, B.; Brechbuehler, H. Ger Offen. 2,343,526; File date, March 14, 1974, Chem. Abstr. 1974, 80, 146185n;
12. (c) Von Bredow, B.; Brechbuehler, H. Ger Offen. 2,446,900; File date, April 10, 1975, Chem. Abstr. 1975, 83, 58835f.
13. (a) Mallakpour, S. E. J. Chem. Edu. 1992, 69, 238;
14. (b) Mallakpour, S.; Rafiee, Z. J. Appl. Polym. Sci. 2004, 91, 2103;
15. (c) Mallakpour, S.; Rafiee, Z. J. Appl. Polym. Sci. 2003, 90, 2861;
16. (d) Mallakpour, S. E.; Rostamizadeh, H. J. Appl. Polym. Sci. 2001, 80, 1335;
17. (e) Mallakpour, S. E.; Nasr-Isfahani, H. J. Appl. Polym. Sci. 2001, 82, 3177;
18. (f ) Mallakpour, S. E.; Sheikholeslami, B. Polym. Int. 1999, 48, 41.
19. Giesecke, H.; Merten, R.; Rottmaier, L. Ger Offen. DE 3,027,612 File date, Feb. 18, 1985; 1982, 96, 182879f.
20. Oikawa, M.; Ebina, C.; Inui, N.; Nagasaki, H.; Yago, S. JP 4, 249, 552 Jpn., File date, Sep. 4, 1992, Chem. Abstr. 1993, 118, 61373a.
21. Rottmaier, L.; Merten, R. Ger offen. 3,106,944. Chem. Abstr. 1982, 97, 198209u. File date, Sep 9, 1982.
22. (a) Zolfigol, M. A.; Torabi, M.; Mallakpour, S. E. Tetrahedron 2001, 57, 8381;
23. (b) Zolfigol, M. A.; Zebarjadian, M. H.; Chehardoli, G.; Mallakpour, S. E.; Shamsipur, M. Tetrahedron 2001, 57, 1627;
24. (c) Zolfigol, M. A.; Chehardoli, G. A.; Mallakpour, S. E. Synth. Commun. 2003, 33, 833;
25. (d) Zolfigol, M. A.; Chehardoli, G. A.; Mallakpour, S. E.; Nasr-Isfahani, H. Synth. Commun. 2001, 31, 1965;
26. (e) Zolfigol, M. A.; Mallakpour, S. E.; Madrakian, E.; Ghaemi, E. Indian J. Chem. 2000, 39B, 308.
27. (a) Mallakpour, S. E.; Asghari, J. Indian J. Chem. 2002, 41B, 812;
28. (b) Mallakpour, S. E.; Asghari, J.; Schollmeyer, D. Polym. Int. 1996, 41;
29. (c) Mallakpour, S. E.; Zolfigol, M. A. J. Sci IR Iran 1993, 4, 199;
30. (d) Mallakpour, S. E.; Hajipour, A. R.; Mahdavian, A. R.; Khoee, S. J. Appl. Polym. Sci. 2000, 76, 240.
31. Zolfigol, M. A.; Azarifar, D.; Mallakpour, S.; Mohammadpoor-Baltork, I.; Forghaniha, A.; Malekia, B.; Abdollahi-Alibeik, M. Tetrahedron Lett. 2006, 47, 833.
32. Gross, A. G.; Deppe, H.; Schober, A. Tetrahedron Lett. 2003, 44, 3939.
33. Cookson, R. C.; Gilani, S. S.; Stevens, I. D. R.; Watts, C. T. Org. Synth. 1971, 51, 121.
34. Pesson, M.; Dupin, S. Bull. Soc. Chim. France 1962, 250.
35. Cookson, R. C.; Gupte, S. S.; Stevens, I. D. R.; Watts, C. T. Org. Synth. Collect. 1988, 6, 936.
36. Arya, V. P.; Shenoy, S. J. Indian J. Chem. 1976, 14B, 883.
37. Tsuji, T. Pharm. Bull. 1954, 2, 403.