Regio- and stereoselective alkoxycarbonylmethylenation of partially saturated heterobicyclic compounds: First synthesis of 2-substituted quinazoline-8-acetic acid esters

Synthetic Communications

Volumn 28, Issue 3, 1998, Pages 475-483

  Zumbrunn, Albrecht ^a,b   Lamberth, Clemens ^a   Schaub, Fritz ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

^b Novartis Crop Protection Ltd   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID ESTER; HETEROCYCLIC COMPOUND; QUINAZOLINE DERIVATIVE;

ALKYLATION; ARTICLE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0031907184     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919808005102     Document Type: Article

References (24)

1. a) Brown, D. J. "The Chemistry of Heterocyclic Compounds, Vol. 55, Quinazolines, Supplement I", Wiley, New York, 1996;
2. b) Armarego, W. L. F., Adv. Heterocycl. Chem. 1979, 24, 1;
3. c) Armarego, W. L. F. "The Chemistry of Heterocyclic Compounds, Vol. 24, Quinazolines", Wiley, New York, 1967.
4. Honkanen, E.; Pippuri, A.; Kairisalo, P.; Thaler, H.; Koivisto, M.; Tuomi, S. J. Heterocycl. Chem. 1980, 17, 797.
5. Dekeyser, M. A.; Downer, R. G. H. Pestic. Sci. 1994, 40, 85.
6. a) Sasse, K. Synthesis 1978, 379;
7. b) Gilchrist, T. L.; Moody, C. J.; Rees, C. W. J. Chem. Soc. Perkin Trans. 1 1975, 1964;
8. c) Brown, D. J.; England, B. T. Aust. J. Chem. 1968, 21, 2813;
9. d) Tsuda, K.; Ikuma, S.; Kawamura, M.; Tachikawa, R.; Baba, Y.; Miyadera, T. Chem. Pharm. Bull. 1962, 10, 856;
10. e) Troeger, J.; Sabewa, V. J. Prakt. Chem. 1927, 117, 117.
11. a) Klemm, L. H.; Wang, J.; Sur, S. K. J. Heterocycl. Chem. 1990, 27, 1537;
12. b) Royals, E. E.; Brannock, K. C. J. Am. Chem. Soc. 1953, 75, 2050.
13. a) Judkins, B. D.; Allen, D. G.; Cook, T. A.; Evans, B.; Sardharwala, T. E. Synth. Commun. 1996, 26, 4351;
14. b) Garigipati, R. S. Tetrahedron Lett. 1990, 31, 1969.
15. Baumgarten, H. E.; Creger, P. L.; Villars, C. E. J. Am. Chem. Soc. 1958, 80, 6609.
16. For similar reactions of other glyoxylic acid derivatives see: a) Laugraud, S.; Guingant, A.; d'Angelo, J. J. Org. Chem. 1987, 52, 4788; b) Barco, A.; Benetti, S.; Baraldi, P. G.; Simoni, D. Synthesis 1981, 199.
17. For similar reactions of other glyoxylic acid derivatives see: a) Laugraud, S.; Guingant, A.; d'Angelo, J. J. Org. Chem. 1987, 52, 4788; b) Barco, A.; Benetti, S.; Baraldi, P. G.; Simoni, D. Synthesis 1981, 199.
18. a) Novak, L.; Rohaly, J.; Poppe, L.; Hornyanszky, G.; Kolonits, P.; Zelei, I.; Feher, I.; Fekete, J.; Szabo, E.; Zahorszky, U.; Javor, A.; Szantay, C. Liebigs Ann. Chem. 1992, 145;
19. b) Strekowski, L.; Visnick, M.; Battiste, M. A. Tetrahedron Lett. 1984, 25, 5603.
20. a) Sakamoto, T.; Sakasai, T.; Yoshizawa, H.; Tanji, K.-I.; Nishimura, S.; Yamanaka, H. Chem. Pharm. Bull. 1983, 31, 4554;
21. b) Bredereck, H.; Simchen, G.; Speh, P., Liebigs Ann. Chem. 1970, 737, 39.
22. Koyama, T.; Hirota, T.; Basho, C.; Watanabe, Y.; Kitauchi, Y.; Satoh, Y.; Ohmori, S.; Yamato, M. Chem. Pharm. Bull. 1976, 24, 1459.
23. a) Hutchings, M. G.; Chippendale, A. M.; Ferguson, I. Tetrahedron 1988, 44, 3727;
24. b) Wood, J. L.; Khatri, N. A.; Weinreb, S. M. Tetrahedron Lett. 1979, 4907.