Carba-Hantzsch synthesis of cyclohexadiene- and biphenylcarboxylic esters

Synthesis

Volumn , Issue 12, 1998, Pages 1807-1811

  Urbahns, Klaus ^a   Kieck, Dieter ^a   Göhrt, Axel ^b  

^a BAYER AG   (Germany)

^b NONE

Author keywords

Biphenyls; Carba Hantzsch; Cyclohexadienes; Isoelectronic analogs; Michael Wittig tandem reaction

Indexed keywords

BIPHENYL DERIVATIVE; BIPHENYLCARBOXYLIC ESTER DERIVATIVE; CYCLOHEXA 1,4 DIENE DERIVATIVE; CYCLOHEXANE DERIVATIVE; DIHYDROPYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0032429514     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-2215     Document Type: Article

References (28)

1. Hantzsch, A. J. Liebigs Ann. Chem. 1882, 215, 1.
2. Goldmann, S.; Stoltefuß, J. Angew. Chem. 1991, 103, 1587.
3. Wolinsky, J.; Hauer, H. S. J. Org. Chem. 1969, 34, 3169.
4. Take, K.; Okumura, K.; Kato, M.; Ohtsuka, M.; Shiokawa, Y. Chem. Pharm. Bull. 1991, 39, 2915. Diercks, R.; tom Dieck, H. Z. Naturforsch. 1984, 39b, 180. Sakakibara, T.; Tanaka, Y.; Yamasaki, S. Chem. Lett. 1986, 797.
5. Take, K.; Okumura, K.; Kato, M.; Ohtsuka, M.; Shiokawa, Y. Chem. Pharm. Bull. 1991, 39, 2915. Diercks, R.; tom Dieck, H. Z. Naturforsch. 1984, 39b, 180. Sakakibara, T.; Tanaka, Y.; Yamasaki, S. Chem. Lett. 1986, 797.
6. Take, K.; Okumura, K.; Kato, M.; Ohtsuka, M.; Shiokawa, Y. Chem. Pharm. Bull. 1991, 39, 2915. Diercks, R.; tom Dieck, H. Z. Naturforsch. 1984, 39b, 180. Sakakibara, T.; Tanaka, Y.; Yamasaki, S. Chem. Lett. 1986, 797.
7. Meyer, H.; Bossert, F.; Horstmann, H. Liebigs Ann. Chem. 1977, 1888.
8. Selected reactions of allylidenephosphoranes with Michael acceptors: Bennani, Y. L.; Boehm, M. F. J. Org. Chem. 1995, 60, 1195. Hatanaka, M.; Himeda, Y.; Ueda, I. Tetrahedron Lett. 1991, 32, 4521. Himeda, Y.; Hatanaka, M.; Ueda, I. J. Chem. Soc., Chem Commun. 1995, 449. Büchi, G.; Wüest, H. Helv. Chim. Acta 1971, 54, 1767.
9. Selected reactions of allylidenephosphoranes with Michael acceptors: Bennani, Y. L.; Boehm, M. F. J. Org. Chem. 1995, 60, 1195. Hatanaka, M.; Himeda, Y.; Ueda, I. Tetrahedron Lett. 1991, 32, 4521. Himeda, Y.; Hatanaka, M.; Ueda, I. J. Chem. Soc., Chem Commun. 1995, 449. Büchi, G.; Wüest, H. Helv. Chim. Acta 1971, 54, 1767.
10. Selected reactions of allylidenephosphoranes with Michael acceptors: Bennani, Y. L.; Boehm, M. F. J. Org. Chem. 1995, 60, 1195. Hatanaka, M.; Himeda, Y.; Ueda, I. Tetrahedron Lett. 1991, 32, 4521. Himeda, Y.; Hatanaka, M.; Ueda, I. J. Chem. Soc., Chem Commun. 1995, 449. Büchi, G.; Wüest, H. Helv. Chim. Acta 1971, 54, 1767.
11. Selected reactions of allylidenephosphoranes with Michael acceptors: Bennani, Y. L.; Boehm, M. F. J. Org. Chem. 1995, 60, 1195. Hatanaka, M.; Himeda, Y.; Ueda, I. Tetrahedron Lett. 1991, 32, 4521. Himeda, Y.; Hatanaka, M.; Ueda, I. J. Chem. Soc., Chem Commun. 1995, 449. Büchi, G.; Wüest, H. Helv. Chim. Acta 1971, 54, 1767.
12. Gedye, R. N.; Westaway, K. C.; Arora, P.; Bisson, R.; Khalil, A. H. Can. J. Chem. 1977, 55, 1218.
13. Ruhemann, S.; Priestley, J. G. J. Chem. Soc. 1909, 95, 109. Ruhemann, S.; Priestley, J. G. J. Chem. Soc. 1909, 95, 449.
14. Ruhemann, S.; Priestley, J. G. J. Chem. Soc. 1909, 95, 109. Ruhemann, S.; Priestley, J. G. J. Chem. Soc. 1909, 95, 449.
15. 3.
16. 3. The structures of 7a and rac-6e were solved using direct methods (SHELXTL-Plus, Siemens Analytical X-Ray Instruments Inc., Madison, WI, 1989) and refined using SHELXL-93 (G. M. Sheldrick, Universität Göttingen, 1993). Further details of the crystal structures are available on request from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ (Fax: +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk (supplementary publication no. CCDC-101076).
17. Selected X-ray structures of 1,4-dihydropyridines: Fossheim, R.; Svarteng, K.; Mostad, A.; Romming, C.; Shefter, E.; Triggle, D. J. J. Med. Chem. 1982, 25, 126. Triggle, A. M.; Shefter, E.; Triggle, D. J. J. Med. Chem. 1980, 23, 1442.
18. Selected X-ray structures of 1,4-dihydropyridines: Fossheim, R.; Svarteng, K.; Mostad, A.; Romming, C.; Shefter, E.; Triggle, D. J. J. Med. Chem. 1982, 25, 126. Triggle, A. M.; Shefter, E.; Triggle, D. J. J. Med. Chem. 1980, 23, 1442.
19. Urbahns, K.; Heine, H.-G.; Junge, B.; Schohe-Loop, R.; Wollweber, H.; Sommermeyer, H.; Glaser, T.; Wittka, R.; De Vry, J. M. V. (Bayer AG) EP 698597, 1996; Chem. Abstr. 1996, 124, 342867c.
20. Meyer, H.; Wehinger, E.; Bossert, F.; Stoepel, K. W.; Vater, W. Arzneim.-Forsch. 1981, 31, 1173. Lee, L. F.; Stikes, G. L.; Gina, L.; Molyneaux, J. M.; Sing, Y.; Larry, Y.; Chupp, J. P.; Woodard, S. S.; Scott, S. J. Org. Chem. 1990, 55, 2872. Atwal, K. S.; Rovnyak, G. C.; Schwartz, J.; Moreland, S.; Hedberg, A.; Gougoutas, J. Z.; Malley, M. F.; Floyd. D. M. J. Med. Chem. 1990, 33, 1510. Wamhoff, H.; Wintersohl, H.; Stölben, S.; Paasch, J.; Zhu, N.; Guo, F. Liebigs Ann. Chem. 1990, 901.
21. Meyer, H.; Wehinger, E.; Bossert, F.; Stoepel, K. W.; Vater, W. Arzneim.-Forsch. 1981, 31, 1173. Lee, L. F.; Stikes, G. L.; Gina, L.; Molyneaux, J. M.; Sing, Y.; Larry, Y.; Chupp, J. P.; Woodard, S. S.; Scott, S. J. Org. Chem. 1990, 55, 2872. Atwal, K. S.; Rovnyak, G. C.; Schwartz, J.; Moreland, S.; Hedberg, A.; Gougoutas, J. Z.; Malley, M. F.; Floyd. D. M. J. Med. Chem. 1990, 33, 1510. Wamhoff, H.; Wintersohl, H.; Stölben, S.; Paasch, J.; Zhu, N.; Guo, F. Liebigs Ann. Chem. 1990, 901.
22. Meyer, H.; Wehinger, E.; Bossert, F.; Stoepel, K. W.; Vater, W. Arzneim.-Forsch. 1981, 31, 1173. Lee, L. F.; Stikes, G. L.; Gina, L.; Molyneaux, J. M.; Sing, Y.; Larry, Y.; Chupp, J. P.; Woodard, S. S.; Scott, S. J. Org. Chem. 1990, 55, 2872. Atwal, K. S.; Rovnyak, G. C.; Schwartz, J.; Moreland, S.; Hedberg, A.; Gougoutas, J. Z.; Malley, M. F.; Floyd. D. M. J. Med. Chem. 1990, 33, 1510. Wamhoff, H.; Wintersohl, H.; Stölben, S.; Paasch, J.; Zhu, N.; Guo, F. Liebigs Ann. Chem. 1990, 901.
23. Meyer, H.; Wehinger, E.; Bossert, F.; Stoepel, K. W.; Vater, W. Arzneim.-Forsch. 1981, 31, 1173. Lee, L. F.; Stikes, G. L.; Gina, L.; Molyneaux, J. M.; Sing, Y.; Larry, Y.; Chupp, J. P.; Woodard, S. S.; Scott, S. J. Org. Chem. 1990, 55, 2872. Atwal, K. S.; Rovnyak, G. C.; Schwartz, J.; Moreland, S.; Hedberg, A.; Gougoutas, J. Z.; Malley, M. F.; Floyd. D. M. J. Med. Chem. 1990, 33, 1510. Wamhoff, H.; Wintersohl, H.; Stölben, S.; Paasch, J.; Zhu, N.; Guo, F. Liebigs Ann. Chem. 1990, 901.
24. 3 (75 MHz): C(2): δ = 144.94 (142.14); C(3): δ = 103.32 (125.71); COOMe: δ = 167.71 (166.93).
25. Hankovszky, O. H.; Sar, C. P.; Hideg, K.; Jerkovich, G. Synthesis 1991, 91. Saalfrank, R. W.; Reihs, S.; Hug, M. Tetrahedron Lett. 1993, 34, 6033. Kuhn, R.; Butula, L. J. Liebigs Ann. Chem. 1968, 718, 50.
26. Hankovszky, O. H.; Sar, C. P.; Hideg, K.; Jerkovich, G. Synthesis 1991, 91. Saalfrank, R. W.; Reihs, S.; Hug, M. Tetrahedron Lett. 1993, 34, 6033. Kuhn, R.; Butula, L. J. Liebigs Ann. Chem. 1968, 718, 50.
27. Hankovszky, O. H.; Sar, C. P.; Hideg, K.; Jerkovich, G. Synthesis 1991, 91. Saalfrank, R. W.; Reihs, S.; Hug, M. Tetrahedron Lett. 1993, 34, 6033. Kuhn, R.; Butula, L. J. Liebigs Ann. Chem. 1968, 718, 50.
28. Molina, P., Pastor, A.; Vilaplana, M. J. J. Org. Chem. 1996, 61, 8094.