A new quinazoline synthesis

Synlett

Volumn , Issue 12, 1999, Pages 1993-1995

  Kotsuki, Hiyoshizo ^a   Sakai, Hiromitsu ^a   Morimoto, Hanae ^a   Suenaga, Hitoshi ^b  

^a KOCHI UNIVERSITY   (Japan)

^b Teikoku Chem Industries Co Ltd   (Japan)

Author keywords

Amidines; O fluorobenzaldehydes; Quinazolines; S(N)Ar

Indexed keywords

QUINAZOLINE; QUINAZOLINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; POLYMERIZATION;

EID: 0032714947     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2998     Document Type: Article

References (26)

1. Johne, S. In "Progress In the Chemistry of Organic Natural Products;" Herz, W.; Grisebach, H.; Kirby, G. W.; Tamm, Ch., Eds.; Springer-Verlag: Wien (1984); Vol. 46, pp 159-229. Johne, S. In "The Alkaloids, Chemistry and Pharmacology;" Brossi, A., Ed.; Academic Press: New York (1986); Vol. 29, pp 99-140.
2. Johne, S. In "Progress In the Chemistry of Organic Natural Products;" Herz, W.; Grisebach, H.; Kirby, G. W.; Tamm, Ch., Eds.; Springer-Verlag: Wien (1984); Vol. 46, pp 159-229. Johne, S. In "The Alkaloids, Chemistry and Pharmacology;" Brossi, A., Ed.; Academic Press: New York (1986); Vol. 29, pp 99-140.
3. Armarego, W. M. F. In "Fused Pyrimidines, Part 1: Quinazolines;" Brown, D. J., Ed., Interscience: New York (1967). Armarego, W. L. F. Adv. Heterocycl. Chem. 1979, 24, 1-62. Shaban, M. A. E.; Taha, M. A. M.; Sharshira, E. M. Adv. Heterocycl Chem. 1991, 52, 1-153. Brown, D. J. "Quinazolines, Suppl. I;" Interscience: New York (1996).
4. Armarego, W. M. F. In "Fused Pyrimidines, Part 1: Quinazolines;" Brown, D. J., Ed., Interscience: New York (1967). Armarego, W. L. F. Adv. Heterocycl. Chem. 1979, 24, 1-62. Shaban, M. A. E.; Taha, M. A. M.; Sharshira, E. M. Adv. Heterocycl Chem. 1991, 52, 1-153. Brown, D. J. "Quinazolines, Suppl. I;" Interscience: New York (1996).
5. Armarego, W. M. F. In "Fused Pyrimidines, Part 1: Quinazolines;" Brown, D. J., Ed., Interscience: New York (1967). Armarego, W. L. F. Adv. Heterocycl. Chem. 1979, 24, 1-62. Shaban, M. A. E.; Taha, M. A. M.; Sharshira, E. M. Adv. Heterocycl Chem. 1991, 52, 1-153. Brown, D. J. "Quinazolines, Suppl. I;" Interscience: New York (1996).
6. Armarego, W. M. F. In "Fused Pyrimidines, Part 1: Quinazolines;" Brown, D. J., Ed., Interscience: New York (1967). Armarego, W. L. F. Adv. Heterocycl. Chem. 1979, 24, 1-62. Shaban, M. A. E.; Taha, M. A. M.; Sharshira, E. M. Adv. Heterocycl Chem. 1991, 52, 1-153. Brown, D. J. "Quinazolines, Suppl. I;" Interscience: New York (1996).
7. Akazome, M.; Yamamoto, J.; Kondo, T.; Watanabe, Y. J. Organomet. Chem. 1995, 494, 229-233.
8. Eguchi, S.; Suzuki, T.; Okawa, T.; Matsushita, Y.; Yashima, E.; Okamoto, Y. J. Org. Chem. 1996, 61, 7316-7319.
9. Kotsuki, H.; Kobayashi, S.; Suenaga, H.; Nishizawa, H. Synthesis 1990, 1145-1147. Kotsuki, H.; Kobayashi, S.; Matsumoto, K.; Suenaga, H.; Nishizawa, H. Synthesis 1990, 1147-1148. For a review see: Kotsuki, H. Kagaku to Kogyo (Osaka) 1994, 68, 265-278.
10. Kotsuki, H.; Kobayashi, S.; Suenaga, H.; Nishizawa, H. Synthesis 1990, 1145-1147. Kotsuki, H.; Kobayashi, S.; Matsumoto, K.; Suenaga, H.; Nishizawa, H. Synthesis 1990, 1147-1148. For a review see: Kotsuki, H. Kagaku to Kogyo (Osaka) 1994, 68, 265-278.
11. Kotsuki, H.; Kobayashi, S.; Suenaga, H.; Nishizawa, H. Synthesis 1990, 1145-1147. Kotsuki, H.; Kobayashi, S.; Matsumoto, K.; Suenaga, H.; Nishizawa, H. Synthesis 1990, 1147-1148. For a review see: Kotsuki, H. Kagaku to Kogyo (Osaka) 1994, 68, 265-278.
12. Amidine derivatives are readily available from the corresponding nitrile precursors and normally used as their HCl salts: Gautier, J.-A.; Miocque, M.; Farnoux, C. C. In "The Chemistry of Amidines and Imidates;" Patai, S., Ed., Wiley: New York (1975); Chapter 7. Tennant, G. In "Comprehensive Organic Chemistry;" Barton, D.; Ollis, W. D., Eds., Pergamon Press: Oxford (1979); Vol. 2, Part 8.1.5.
13. Amidine derivatives are readily available from the corresponding nitrile precursors and normally used as their HCl salts: Gautier, J.-A.; Miocque, M.; Farnoux, C. C. In "The Chemistry of Amidines and Imidates;" Patai, S., Ed., Wiley: New York (1975); Chapter 7. Tennant, G. In "Comprehensive Organic Chemistry;" Barton, D.; Ollis, W. D., Eds., Pergamon Press: Oxford (1979); Vol. 2, Part 8.1.5.
14. NAr reaction is the rate-determining step in this transformation because of its less reactivity: Bunnett, J. F.; Zahler, R. E. Chem. Rev. 1951, 49, 273-412. Miller, J. "Aromatic Nucleophilic Substitution;" Elsevier: New York (1968). March, J. "Advanced Organic Chemistry;" 4th Ed., Wiley: New York (1992); Chapter 13. Paradisi, C. In "Comprehensive Organic Synthesis;" Trost, B. M.; Fleming I., Eds., Pergamon Press: Oxford (1991); Vol. 4, Part 2.1.
15. NAr reaction is the rate-determining step in this transformation because of its less reactivity: Bunnett, J. F.; Zahler, R. E. Chem. Rev. 1951, 49, 273-412. Miller, J. "Aromatic Nucleophilic Substitution;" Elsevier: New York (1968). March, J. "Advanced Organic Chemistry;" 4th Ed., Wiley: New York (1992); Chapter 13. Paradisi, C. In "Comprehensive Organic Synthesis;" Trost, B. M.; Fleming I., Eds., Pergamon Press: Oxford (1991); Vol. 4, Part 2.1.
16. NAr reaction is the rate-determining step in this transformation because of its less reactivity: Bunnett, J. F.; Zahler, R. E. Chem. Rev. 1951, 49, 273-412. Miller, J. "Aromatic Nucleophilic Substitution;" Elsevier: New York (1968). March, J. "Advanced Organic Chemistry;" 4th Ed., Wiley: New York (1992); Chapter 13. Paradisi, C. In "Comprehensive Organic Synthesis;" Trost, B. M.; Fleming I., Eds., Pergamon Press: Oxford (1991); Vol. 4, Part 2.1.
17. NAr reaction is the rate-determining step in this transformation because of its less reactivity: Bunnett, J. F.; Zahler, R. E. Chem. Rev. 1951, 49, 273-412. Miller, J. "Aromatic Nucleophilic Substitution;" Elsevier: New York (1968). March, J. "Advanced Organic Chemistry;" 4th Ed., Wiley: New York (1992); Chapter 13. Paradisi, C. In "Comprehensive Organic Synthesis;" Trost, B. M.; Fleming I., Eds., Pergamon Press: Oxford (1991); Vol. 4, Part 2.1.
18. Kikelj, J. In Houben-Weyl Methods of Organic Chemistry, Schaumann, E., Ed.; Georg Thieme Verlag: Stuttgart, Vol. E 9b/2, 1998; pp 68-69. See also, Kraus, G. A.; Maeda, H. Tetrahedron Lett. 1994, 35, 9189-9190.
19. Kikelj, J. In Houben-Weyl Methods of Organic Chemistry, Schaumann, E., Ed.; Georg Thieme Verlag: Stuttgart, Vol. E 9b/2, 1998; pp 68-69. See also, Kraus, G. A.; Maeda, H. Tetrahedron Lett. 1994, 35, 9189-9190.
20. Satisfactory spectral and analytical data were obtained for all new compounds.
21. 3: C, 78.74%; H, 5.05%; N, 16.20%; Found: C, 78.93%; H, 5.12%; N, 16.29%.
22. 4.
23. 3N.
24. Prepared from p-fluorobenzonitrile via fluorine-directed lithiation followed by formylation: Bridges, A. J.; Lee, A.; Maduakor, E. C.; Schwartz, C. E. Tetrahedron Lett. 1992, 33, 7499-7502.
25. 1a was completely consumed under these conditions, and the use of more 2a did not increase the product yield.
26. Prepared by nitration of o-fluorobenzaldehyde: Gale, D. J.; Wilshire, J. F. K. Aust. J. Chem. 1970, 23, 1063-1068.