Access to variously substituted 5,6,7,8-tetrahydro-3H-quinazolin-4-ones via Diels-Alder adducts of phenyl vinyl sulfone to cyclobutene-annelated pyrimidinones

European Journal of Organic Chemistry

Volumn , Issue 12, 2006, Pages 2753-2765

  Dalai, Suryakanta ^a   Belov, Vladimir N ^a,b   Nizamov, Shamil ^a,b   Rauch, Karsten ^a   Finsinger, Dirk ^c   De Meijere, Armin ^a,b  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b KAdemCustomChem GmbH   (Germany)

^c MERCK KGAA   (Germany)

Author keywords

5,6,7,8 Tetrahydro 3H quinazolin 4 ones; Cycloaddition; Michael addition; Nitrogen heterocycles

Indexed keywords

EID: 33745638596     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600060     Document Type: Article

References (32)

1. R. Koehler, L. Goodman, J. DeGraw, B. R. Baker, J. Am. Chem. Soc. 1958, 80, 5779-5786.
2. a) A. Gangjee, A. Vasudevan, R. L. Kisliuk, J. Heterocycl. Chem. 1997, 34, 1669-1676;
3. b) G. Bernáth, J. Kóbor, J. Lázár, F. Fülöp, J. Heterocycl. Chem. 1996, 33, 1983-1987;
4. c) G. Bernáth, T. Janáky, G. Göndös, J. Lázár, Z. Ecsery, Pharmazie 1983, 38, 270-271;
5. d) T. Nishio, M. Fujisawa, Y. Omote, J. Chem. Soc., Parkin Trans. 1 1987, 2523-2529.
6. a) T. Sekiya, H. Hiranuma, M. Uchide, S. Hata, S. Yamada, Chem. Pharm. Bull. 1981, 29, 948-954;
7. b) F. Claudi, G. Giorgioni, L. Scoccia, R. Ciccocioppo, I. Panocka, M. Massi, Eur. J. Med. Chem. 1997, 32, 651-660.
8. M. G. Nair, R. Dhawan, M. Ghazala, T. I. Kalman, R. Ferone, Y. Gaumont, R. L. Kisliuk, J. Med. Chem. 1987, 30, 1256-1261.
9. A. Rosowsky, R. A. Forsch, R. G. Moran, J. Med. Chem. 1989, 32, 709-715.
10. a) S. Kawamura, Y. Sanemitsu, J. Org. Chem. 1993, 58, 414-418;
11. b) F. Fülöp, G. Bernáth, Synthesis 1985, 1148-1149.
12. M. Limbach, S. Dalai, A. de Meijere, Adv. Synth. Catal. 2004, 346, 760-766.
13. For a review on the chemistry of methyl 2-chloro-2- cyclopropylideneacetate (5) see: A. de Meijere, S. I. Kozhushkov, L. P. Hadjiarapoglou, Top. Curr. Chem. 2000, 207, 149-227.
14. M. W. Nötzel, K. Rauch, T. Labahn, A. de Meijere, Org. Lett. 2002, 4, 839-841.
15. a) R. V. C. Carr, L. A. Paquette, J. Am. Chem. Soc. 1980, 102, 853-855;
16. b) R. V. C. Carr, R. V. Williams, L. A. Paquette, J. Org. Chem. 1983, 48, 4976-4986.
17. a) E. J. Bush, D. W. Jones, J. Chem. Soc., Perkin Trans. 1 1997, 3531-3536;
18. b) E. J. Bush, D. W. Jones, M. Thornton-Pett, Tetrahedron Lett. 1994, 35, 9755-9758;
19. c) T. Kametani, Y. Suzuki, T. Honda, Chem. Pharm. Bull. 1986, 34, 4971-4977.
20. For syntheses of amidines from nitriles see: a) R. A. Moss, J. Terpinski, D. P. Cox, D. Z. Denney, K. Krogh-Jespersen, J. Am. Chem. Soc. 1985, 107, 2743-2748;
21. b) R. T. Boeré, R. T. Oakley, R. W. Reed, J. Organomet. Chem. 1987, 331, 161-167;
22. c) F. C. Shaefer, A. P. Krapcho, J. Org. Chem. 1962, 27, 1255-1258;
23. d) A. Thurkauf, A. Hutchison, J. Peterson, L. Cornfield, R. Meade, K. Huston, K. Harris, P. C. Ross, K. Gerber, T. V. Ramabhadran, J. Med. Chem. 1995, 38, 2251-2255;
24. e) W. von der Saal, R. A. Engh, A. Eichinger, B. Gabriel, R. Kucznierz, J. Sauer, Arch. Pharm. 1996, 329, 73-82.
25. B. M. Trost, H. C. Arndt, P. E. Strege, T. R. Verhoeven, Tetrahedron Lett. 1976, 17, 3477-3478.
26. a) Y. Masaki, Y. Serizawa, K. Nagata, K. Kaji, Chem. Lett. 1984, 2105-2108;
27. b) D. F. Taber, Q. Jiang, B. Chen, W. Zhang, C. L. Campbell, J. Org. Chem. 2002, 67, 4821-4827.
28. A variety of 2′-substituted alkyl 2-chloro-2- cyclopropylideneacetates of type 5 is accessible along the originally developed route to the parent compound 5; cf. T. Liese, S. Teichmann, A. de Meijere, Synthesis 1988, 25-32.
29. The pertinent ring-enlarging rearrangement of a Michael adduct of methyl 2-chloro-2-(2'-methylcyclopropylidene)acetate has previously been reported; cf. L. Wessjohann, K. Giller, B. Zuck, L. Skattebøl, A. de Meijere, J. Org. Chem. 1993, 58, 6442-6450.
30. T. Sekiya, H. Hiranuma, M. Uchide, S. Hata, S.-I. Yamada, Chem. Pharm. Bull. 1981, 29, 948-954.
31. E. Rogana, D. L. Nelson, M. Mares-Guia, J. Am. Chem. Soc. 1975, 97, 6844-6848.
32. P. Reynaud, J.-D. Brion, E. Nguyen-Tri-Xuong, C. Davrinche, F. Pieri, M.-L. Arnould-Guerin, Eur. J. Med. Chem. 1989, 24, 427-434.