Synthesis of quinazolines using carbon dioxide (or carbon monoxide with sulfur) under mild conditions

Heteroatom Chemistry

Volumn 11, Issue 6, 2000, Pages 428-433

  Mizuno, Takumi ^a   Okamoto, Noriaki ^a   Ito, Takatoshi ^a   Miyata, Toshiyuki ^a  

^a OSAKA MUNICIPAL TECHNICAL RESEARCH INSTITUTE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CARBON DIOXIDE; CARBON MONOXIDE; CARBONYLATION; POTASH; SULFUR; SYNTHESIS (CHEMICAL);

AMINOBENZONITRILE; CHEMICAL FIXATION; HYDROXYMERCAPTOQUINAZOLINE;

NITROGEN COMPOUNDS;

EID: 0033677513     PISSN: 10427163     EISSN: None     Source Type: Journal    
DOI: 10.1002/1098-1071(2000)11:6<428::AID-HC12>3.0.CO;2-Z     Document Type: Article

References (19)

1. (a) Goto, S.; Tsuboi, H.; Kagara, K. Chem Express 1993, 8, 761-764
2. (b) Kagara, K.; Goto, S.; Tsuboi, H. Jap Pat, 1989, 25767.
3. (a) Pastor, G.; Blanchard, C.; Montginoul, C.; Torreilles, E.; Giral, L.; Texier, A. Bull Soc Chim Fr 1975, 1331-1338
4. (b) Khalifa, M.; Osman, A. N.; Ibrahim, M. G.; Ossman, A. R. E.; Ismail, M. A. Pharmazie 1982, 37, 115-117.
5. Michman, M.; Patai, S.; Wiesel, Y. Org Prep Proced Int 1978, 10, 13-16.
6. Lange, N. A.; Sheibley, F. E. Org Synth 1943, 2, 79-80.
7. Vorbrueggen, H.; Krolikiewicz, K. Tetrahedron 1994, 50, 6549-6558.
8. Miyata, T.; Mizuno, T.; Nagahama, Y.; Nishiguchi, I.; Hirashima, T.; Sonoda, N. Heteroat Chem 1991, 2, 473-475.
9. Mizuno, T.; Okamoto, N.; Ito, T.; Miyata, T. Tetrahedron Lett 2000, 41, 1051-1053.
10. Similar reaction of 6-aminotoyocamycin with carbonyl sulfide in methanolic-sodium hydroxide at high temperature (180°C) was reported [9].
11. Chung, F.-L.; Earl, R. A.; Townsend, L. B. Tetrahedron Lett 1980, 21, 1599-1602.
12. (a) Haruki, E. In Organic and Bio-organic Chemistry of Carbon Dioxide; Inoue, S.; Yamazaki, N. Eds.; Kodansha Ltd.: Tokyo, 1981; pp. 5-78
13. (b) Haruki, E.; Arakawa, M.; Matsumura, N.; Otsuji, Y.; Imoto, E. Chem Lett 1974, 427-428
14. (c) Hori, Y.; Nagano, Y.; Fukuhara, T.; Teramoto, S.; Taniguchi, H. Nippon Kagaku Kaishi 1987, 1408-1413.
15. For the synthesis of 2-hydroxy-4-mercaptoquinazolines 3 using carbon monoxide with sulfur, carbonyl sulfide may be generated in situ from carbon monoxide and sulfur in the presence of base at the first stage of the reaction. Carbonyl sulfide reacts with 2-aminobenzonitriles 2 in a similar manner to the preparation of 2,4-dihydroxyquinazolines 1 from 2-aminobenzonitriles 2 with carbon dioxide.
16. Mavrovic, I. In Kirk-Othmer Encyclopedia of Chemical Technology; Mark, H. F., Ed.; Interscience Publishers: New York, 1970; Vol. 21, pp. 37-56.
17. Mizuno, T.; Nishiguchi, I.; Hirashima, T.; Sonoda, N. Heteroat Chem 1990, 1, 157-159.
18. Beilstein, 24, 373.
19. Merck Index, 12, 10193.