Spiroquinazoline support studies: New cascade reactions based on the morin rearrangement

Journal of Organic Chemistry

Volumn 64, Issue 9, 1999, Pages 2990-2991

  Hart, David J ^a   Magomedov, Nabi ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CEPHAM DERIVATIVE; PENAM DERIVATIVE; QUINAZOLINE DERIVATIVE; SPIROQUINAZOLINE; UNCLASSIFIED DRUG;

ANALGESIA; ANTIFUNGAL ACTIVITY; ARTICLE; ASPERGILLUS; CHEMICAL REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0033617278     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990147c     Document Type: Article

References (31)

1. This paper is dedicated to Professor Harold Hart on the occasion of his 77th birthday.
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9. 3 bond of indoles, see: Buchi, G.; DeShong, P. R.; Katsumura, S.; Sugimura, Y. J. Am. Chem. Soc. 1979, 101, 5084. Nakagawa, M.; Taniguchi, M.; Sodeoka, M.; Ito, M.; Yamaguchi, K.; Hino T. J. Am. Chem. Soc. 1983, 105, 3709. He, F.; Foxman, B. M.; Snider, B. B. J. Am. Chem. Soc. 1998, 120, 6417.
10. 3 bond of indoles, see: Buchi, G.; DeShong, P. R.; Katsumura, S.; Sugimura, Y. J. Am. Chem. Soc. 1979, 101, 5084. Nakagawa, M.; Taniguchi, M.; Sodeoka, M.; Ito, M.; Yamaguchi, K.; Hino T. J. Am. Chem. Soc. 1983, 105, 3709. He, F.; Foxman, B. M.; Snider, B. B. J. Am. Chem. Soc. 1998, 120, 6417.
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17. Attempts to ionize sulfoxide 9 using a variety of electrophiles such as iodomethane, silver triflate, and mercuric triflate have failed thus far.
18. The stereochemistry assigned to 9 in Scheme 2 is tentative and only reflects our expectations based on steric considerations.
19. For relevant studies of the Morin rearrangement, see: Chioccara, F.; Oliva, L.; Prota, G.; Novellino, E. Synthesis 1978, 744. Ueda, N.; Shimizu, H.; Kataoka, T.; Hori, M. Tetrahedron Lett. 1984, 25, 757. Lee, W. S.; Hahn, H. G.; Nam, K. D. J. Org. Chem. 1986, 51, 2789. Mah, H. D.; Lee, W. S. J. Heterocyclic. Chem. 1989, 26, 1447. Mah, H.; Nam, K. D.; Hahn, H.-G. Heterocycles 1997, 45, 1999.
20. For relevant studies of the Morin rearrangement, see: Chioccara, F.; Oliva, L.; Prota, G.; Novellino, E. Synthesis 1978, 744. Ueda, N.; Shimizu, H.; Kataoka, T.; Hori, M. Tetrahedron Lett. 1984, 25, 757. Lee, W. S.; Hahn, H. G.; Nam, K. D. J. Org. Chem. 1986, 51, 2789. Mah, H. D.; Lee, W. S. J. Heterocyclic. Chem. 1989, 26, 1447. Mah, H.; Nam, K. D.; Hahn, H.-G. Heterocycles 1997, 45, 1999.
21. For relevant studies of the Morin rearrangement, see: Chioccara, F.; Oliva, L.; Prota, G.; Novellino, E. Synthesis 1978, 744. Ueda, N.; Shimizu, H.; Kataoka, T.; Hori, M. Tetrahedron Lett. 1984, 25, 757. Lee, W. S.; Hahn, H. G.; Nam, K. D. J. Org. Chem. 1986, 51, 2789. Mah, H. D.; Lee, W. S. J. Heterocyclic. Chem. 1989, 26, 1447. Mah, H.; Nam, K. D.; Hahn, H.-G. Heterocycles 1997, 45, 1999.
22. For relevant studies of the Morin rearrangement, see: Chioccara, F.; Oliva, L.; Prota, G.; Novellino, E. Synthesis 1978, 744. Ueda, N.; Shimizu, H.; Kataoka, T.; Hori, M. Tetrahedron Lett. 1984, 25, 757. Lee, W. S.; Hahn, H. G.; Nam, K. D. J. Org. Chem. 1986, 51, 2789. Mah, H. D.; Lee, W. S. J. Heterocyclic. Chem. 1989, 26, 1447. Mah, H.; Nam, K. D.; Hahn, H.-G. Heterocycles 1997, 45, 1999.
23. For relevant studies of the Morin rearrangement, see: Chioccara, F.; Oliva, L.; Prota, G.; Novellino, E. Synthesis 1978, 744. Ueda, N.; Shimizu, H.; Kataoka, T.; Hori, M. Tetrahedron Lett. 1984, 25, 757. Lee, W. S.; Hahn, H. G.; Nam, K. D. J. Org. Chem. 1986, 51, 2789. Mah, H. D.; Lee, W. S. J. Heterocyclic. Chem. 1989, 26, 1447. Mah, H.; Nam, K. D.; Hahn, H.-G. Heterocycles 1997, 45, 1999.
24. The stereochemistry assigned to 13 in Scheme 3 is tentative and only reflects our expectations based on steric considerations.
25. Attempts to detect the product analogous to 14 in the rearrangement of 9 were unsuccessful.
26. The yields represent the range obtained over several runs.
27. Independent treatment of 16 and 17 with trifluoroacetic acid-chloroform at 65 °C for 30 min provided a 1:2 mixture of 16 and 17, respectively. Thus, the partitioning of 13 between 16 and 17 appears to reflect the relative thermodynamic stability of these isomers.
28. This would necessarily provide the sulfoxide stereochemistry shown in Scheme 3. This stereochemistry has not been proven. Cooper, R. D. G. J. Am. Chem. Soc. 1970, 92, 5010.
29. It is possible that the conversion of 19 to 15 involves formation of a spiroindoline intermediate followed by a Wagner-Meerwein shift rather than the simple mechanism depicted in Scheme 3.
30. For a relevant cyclization, see: Ottenheijm, H. C. J.; Plate, R.; Noordik, J. H.; Herscheid, J. D. M. J. Org. Chem. 1982, 47, 2147.
31. For a Pummerer/N-acyliminium ion cyclization sequence, see: Padwa, A.; Waterson, A. G. Tetrahedron Lett. 1998, 39, 8585.