Dimerization of substituted 2-aminobenzoic acids under Vilsmeier conditions: A novel route to the synthesis of 4-(3H)-quinazolinones

Tetrahedron Letters

Volumn 37, Issue 28, 1996, Pages 5015-5018

  Majo, Vattoly J ^a   Perumal, Paramasivan T ^a  

^a CENTRAL LEATHER RESEARCH INSTITUTE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ANTHRANILIC ACID DERIVATIVE; QUINAZOLINONE DERIVATIVE;

ANALGESIC ACTIVITY; ANTICOAGULATION; ANTIINFLAMMATORY ACTIVITY; ARTICLE; DIMERIZATION; DRUG ACTIVITY; DRUG SYNTHESIS;

EID: 0030575412     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01022-2     Document Type: Article

References (28)

1. 1. (a) Armarego, W. L. F. Adv. Heterocycl. Chem. 1963, 1, 253-309.
2. (b) Armarego, W. L. F. Adv. Heterocycl. Chem. 1979, 24, 1-62.
3. 2. (a) Srivastava, B.; Shukla, J. S. Indian J. Chem. Sect. B. 1991, 30B, 332-339.
4. (b) Fisnerova, L.; Brunova, B.; Kocfeldova, Z.; Tikalova, J.; Maturova, E.; Grimova, J. Collect. Czech. Chem. Commun. 1991, 56, 2373-2381.
5. (c) Saxena, S.; Verma, M.; Saxena, A. K.; Shanker, K. Indian J. Pharm. Sci. 1991, 53, 48-52.
6. (d) Abdel-Rahman, M. M.; Mangoura, S. A.; El-Bitar, H. I. Bull. Pharm. Sci. Assiut. Univ. 1990, 13, 137-144; Chem Abstr. 1992, 116, 185c
7. (d) Abdel-Rahman, M. M.; Mangoura, S. A.; El-Bitar, H. I. Bull. Pharm. Sci. Assiut. Univ. 1990, 13, 137-144; Chem Abstr. 1992, 116, 185c
8. (e) Gravier, D.; Dupin, J. P.; Casadebaig, F.; Hou, G.; Boisseau, M.; Bernard, H. Pharmazie. 1992, 47, 91-94.
9. 3. (a) Hisano, T.; Shoji, K.; Ichikawa, M. Org. Prep. Proced. Int. 1975, 7, 271-275.
10. (b) Errede, L. A.; Mc. Brady, J. J.; Oien, H. T. J. Org. Chem. 1977, 42, 656-658.
11. (c) Schweizer, E. E.; De Voe Goff, S.; Murray, W. P. J. Org. Chem. 1977, 42, 200-205.
12. (d) Paterson, T. Mc. C.; Smalley, R. K.; Suschitzky, H. Synthesis, 1975, 187-189.
13. 4. (a) for a recent review see Marson, C. M. Tetrahedron 1992, 48, 3659-3726.
14. (b) Jutz, C. In Advances in Organic Chemistry; Taylor, E. C. Ed.; John Wiley & Sons, New York, 1976, Vol.9, pp 225-342.
15. (c) Seshadri, S. J. Sci. Ind. res. 1973, 32, 128-149.
16. (d) Burn, D. Chem. Ind. (London) 1973, 870-873.
17. (e) Church, R.; Trust, R.; Albright, J. D.; Powell, D. W. J. Org. Chem, 1995, 60, 3750.
18. 5. (a) Meth-Cohn, O.; Tarnowski, B. Adv. Heterocycl. Chem. 1982, 31, 207-236.
19. (b) Meth-Cohn, O. Heterocycles, 1993, 35, 539-557.
20. (c) Meth-Cohn, O.; Taylor, D. L. Tetrahedron Lett. 1993, 34, 3629-3632.
21. (d) Jackson, A.; Meth-Cohn, O. J. Chem. Soc., Chem. Commun. 1995, 1319.
22. (e) Meth-Cohn. O.; Taylor, D. L. J. Chem. Soc. Chem. Commun. 1995, 1463-1464.
23. (f) Megati, S.; Rao, K. G. S. Tetrahedron Lett. 1995, 36, 5819.
24. 6. (a) Balasundaram, B.; Venugopal, M.; Perumal, P. T. Tetrahedron Lett. 1993, 34, 4249-4252.
25. (b) Venugopal, M.; Perumal, P. T. Synth. Commun. 1991, 21, 515-519.
26. (c) Venugopal, M.; Umarani, R.; Perumal, P. T.; Rajadurai, S. Tetrahedron Lett. 1991, 32, 3235-3238.
27. 2: C, 69.60; H, 5.16; N, 14.33. Found : C, 69.94; H, 5.30; N, 14.63.
28. 8. Cassey, A. L.; Harris, R. L. N.; Huppatz, J. L.: Phillips, J. N. Angew. Chem. Int. Ed. Engl. 1972, 11, 1098-1099.