A New Synthesis of Aryl Substituted Quinazolin-4(1H)-ones

Journal of Heterocyclic Chemistry

Volumn 33, Issue 6, 1996, Pages 2051-2053

  Roth, Gary A ^a   Tai, Jimmy J ^a  

^a DOW CHEMICAL COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0008359132     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570330680     Document Type: Article

References (13)

1. For selected examples of the uses of quinazolin-4(1H)-ones as pharmaceutical and Agro chemical intermediates see: N. Singhal, I. S. Gupta and P. C. Bansal, J. Indian Chem. Soc., 61, 690 (1984). R. A. LeMahieu, M. Carson, W. C. Nason, D. R. Parrish, A. F. Wleton, H. W. Baruth and B. Yaremko, J. Med. Chem., 26, 420 (1983). J. J. Tai, J. W. Ringer, K. L. Krumel and R. C. Krauss, US Patent 5,214,144 (1993).
2. For selected examples of the uses of quinazolin-4(1H)-ones as pharmaceutical and Agro chemical intermediates see: N. Singhal, I. S. Gupta and P. C. Bansal, J. Indian Chem. Soc., 61, 690 (1984). R. A. LeMahieu, M. Carson, W. C. Nason, D. R. Parrish, A. F. Wleton, H. W. Baruth and B. Yaremko, J. Med. Chem., 26, 420 (1983). J. J. Tai, J. W. Ringer, K. L. Krumel and R. C. Krauss, US Patent 5,214,144 (1993).
3. For selected examples of the uses of quinazolin-4(1H)-ones as pharmaceutical and Agro chemical intermediates see: N. Singhal, I. S. Gupta and P. C. Bansal, J. Indian Chem. Soc., 61, 690 (1984). R. A. LeMahieu, M. Carson, W. C. Nason, D. R. Parrish, A. F. Wleton, H. W. Baruth and B. Yaremko, J. Med. Chem., 26, 420 (1983). J. J. Tai, J. W. Ringer, K. L. Krumel and R. C. Krauss, US Patent 5,214,144 (1993).
4. W. L. F. Armarego, J. Appl. Chem., 11, 70 (1961).
5. For a general reference see: W. L. F. Armarego, Fused Pyrimidines: Quinazolines, in The Chemistry of Heterocyclic Compounds, Vol 24, D. J. Brown, ed, John Wiley & Sons, New York, 1967, pp 74-102.
6. M. K. McKee, R. L. McKee and R. W. Bost, J. Am. Chem. Soc., 69, 184 (1947).
7. J. T. Gupton, K. F. Correia and B. S. Foster, Synth. Commun., 16, 365 (1986).
8. K. Nagahara, K. Takagi and T. Ueda, Chem. Pharm. Bull, 24, 310 (1976).
9. M. T. Bogert and W. F. Hand, J. Am. Chem. Soc., 28, 94 (1906).
10. M. Akazome, J. Yamamoto, T. Kondo and Y. Wantanabe, J. Organomet. Chem., 494, 229 (1995).
11. Most of the 2-aminobenzonitriles utilized in this study were prepared either by the Rosenmund-von Braun cyanation of 2-haloanilines or the aminolysis of 2-fluorobenzonitriles.
12. Quinazolin-4(1H)-ones 2a-h were obtained at 96+ area percent purity by reverse phase hplc analysis. Yields presented in Table I are unoptimized and based on dried materials isolated directly from the reaction mixture. Recrystallization from ethanol/water or N,N-dimethylformamide/water can provide analytically pure materials listed in Table III.
13. For convenience, the 2-aminobenzonitrile may be dissolved in 88% formic acid and added to the reaction via a dropping funnel.