An efficient synthesis of thio- and thiazoloquinazolinones by the electrochemical oxidation of catechols in the presence of 2-mercapto-4(3H)- quinazolinone

Synthesis

Volumn , Issue 24, 2008, Pages 3963-3966

  Fakhari, Ali Reza ^a   Hasheminasab, Kobra ^a   Ahmar, Hamid ^a   Alizadeh, Abdolali ^b  

^a SHAHID BEHESHTI UNIVERSITY   (Iran)

^b TARBIAT MODARES UNIVERSITY   (Iran)

Author keywords

Decarboxylation; Electrochemical synthesis; Heterocycles; Phenols; Thiols

Indexed keywords

CARBOXYLATION; CHEMICAL REACTIONS; DYES; ELECTROCHEMICAL OXIDATION; OXIDATION; PHENOLS; SYNTHESIS (CHEMICAL);

AQUEOUS SOLUTIONS; DECARBOXYLATION; DIHYDROXYBENZOIC ACIDS; EFFICIENT SYNTHESES; ELECTROCHEMICAL SYNTHESIS; ELECTRON TRANSFERS; HETEROCYCLES; THIOLS;

ANODIC OXIDATION;

2 [(3,4 DIHYDROXY 5 METHOXYPHENYL)THIO]QUINAZOLIN 4(3H) ONE; 2 [(4,5 DIHYDROXY 2 METHYLPHENYL)THIO]QUINAZOLIN 4(3H) ONE; 4 METHYLCATECHOL; 8,9 DIHYDROXY 12H BENZOTHIAZOLO (2,3 B)QUINAZOLIN 12 ONE; 8,9 DIHYDROXY 7 METHYL 12H BENZOTHIAZOLO(2,3 B)QUINAZOLIN 12 ONE; CATECHOL DERIVATIVE; HYDROXYBENZOIC ACID DERIVATIVE; QUINAZOLINONE DERIVATIVE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTROCHEMISTRY; ELECTRON TRANSPORT; OXIDATION KINETICS;

EID: 58149331119     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-0028-1083258     Document Type: Article

References (18)

1. Cohen, E.; Klarberg, B.; Vaughan, J. R. J. Am. Chem. Soc. 1960, 82, 2731.
2. Wolf, J. F.; Rathman, T. L.; Sleevi, M. C.; Campbell, J. A.; Greenwood, T. D. J. Med. Chem. 1990, 33, 161.
3. Padia, J. K.; Field, M.; Hinton, J.; Meecham, K.; Pablo, J.; Pinnock, R.; Roth, B. D.; Singh, L.; Suman-Chauhan, N.; Trivedi, B. K.; Webdale, L. J. Med. Chem. 1998, 41, 1042.
4. Lingaiah, B. V.; Ezikiel, G.; Yakaiah, T.; Reddy, G. V.; Rao, P. S. Synlett 2006, 2507.
5. Connolly, D. J.; Guiry, P. J. Synlett 2001, 1707.
6. Mhaske, S. B.; Argade, N. P. Tetrahedron 2006, 62, 9787.
7. Abdel-Jalil, R. J.; Voelter, W.; Saeed, M. Tetrahedron Lett. 2004, 45, 3475.
8. Rewcastle, G. W.; Palmer, B. D.; Bridges, A. J.; Showalter, H. D. H.; Sun, L.; Nelson, J.; McMichael, A.; Kraker, A. J.; Fry, D. W.; Denny, W. A. J. Med. Chem. 1996, 39, 918.
9. Besson, T.; Guillard, J.; Rees, C. W. Tetrahedron Lett. 2000, 41, 1027.
10. Sauter, F.; Frohlich, J.; Chowdhury, A. Z. M. S.; Hametner, C. Monatsh. Chem. 1997, 128, 503.
11. Bouillon, I.; Krchnak, V. J. Comb. Chem. 2007, 9, 912.
12. Dhami, K. S.; Arora, S. S.; Narang, K. S. J. Med. Chem. 1963, 6, 450.
13. LeMahieu, R. A.; Carson, M.; Welton, A. F.; Baruth, H. W.; Yaremko, B. J. Med. Chem. 1983, 26, 107.
14. McCarty, J. E. J. Org. Chem. 1962, 27, 2673.
15. (a) Bose, P. K.; Pathak, K. B. J. Indian Chem. Soc. 1934, 11, 463.
16. (b) Kate, L. J. Am. Chem. Soc. 1958, 76, 712.
17. Papouchado, L.; Petrie, G.; Adams, R. N. J. Electroanal. Chem. 1972, 38, 389.
18. Nematollahi, D.; Rafiee, M.; Samadi-Meybodi, A. Electrochim. Acta 2004, 49, 2495.