Reaction of heterocyclic ketene aminals with bis(methylthio)methylene malononitrile: Synthesis of polyfunctionalized pyridine-fused 1,3-diazaheterocycles from heterocyclic ketene aminals

Synlett

Volumn , Issue 5, 2007, Pages 761-764

  Liao, Jiang Peng ^a,b   Zhang, Ti ^a,b   Yu, Chu Yi ^a   Huang, Zhi Tang ^a  

^a INSTITUTE OF CHEMISTRY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

1,3 diazaheterocycles; Cascade reaction; Heterocyclic ketene aminals; Polyfunctionalized pyridine; Synthesis

Indexed keywords

1,3 DIAZAHETEROCYCLIC COMPOUND; BIS(METHYLTHIO)METHYLENE MALONONITRILE; HETEROCYCLIC COMPOUND; HETEROCYCLIC KETONE; KETENE DERIVATIVE; MALONONITRILE; POLYFUNCTIONAL GROUP; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CRYSTALLOGRAPHY; POLARIZATION; SYNTHESIS;

EID: 34047141012     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-970757     Document Type: Article

References (37)

1. For reviews, see: (a) Huang, Z.-T.; Wang, M.-X. Heterocycles 1994, 37, 1233.
2. (b) Huang, Z.-T.; Wang, M.-X. Prog. Nat. Sci. 2002, 12, 249.
3. (c) For our recent work, see: Yu, C.-Y.; Yang, P.-H.; Zhao, M.-X.; Huang, Z.-T. Synlett 2006, 1835.
4. Huang, Z.-T.; Wang, M.-X. J. Org. Chem. 1992, 57, 184; and references cited therein.
5. (a) Huang, Z.-T.; Wang, M.-X. Synth. Commun. 1991, 21, 1167.
6. (b) Huang, Z.-T.; Wang, M.-X. Synth. Commun. 1991, 21, 1909.
7. Liu, B.; Wang, M.-X.; Huang, Z.-T. Tetrahedron Lett. 1999, 40, 7399.
8. Wang, M.-X.; Liang, J.-M.; Huang, Z.-T. J. Chem. Res., Synop. 1994, 166;
9. J. Chem. Res., Miniprint 1994, 1001.
10. (a) Huang, Z.-T.; Liu, Z.-R. Chem. Ber. 1989, 122, 95.
11. (b) Wang, L.-B.; Yu, C.-Y.; Huang, Z.-T. Synthesis 1994, 1441.
12. (a) Huang, Z.-T.; Tzai, L.-H. Chem. Ber. 1986, 119, 2208.
13. (b) Huang, Z.-T.; Liu, Z.-R. Heterocycles 1986, 24, 2247.
14. (c) Huang, Z.-T.; Wang, M.-X. J. Chem. Soc., Perkin Trans. 1 1993, 1085; and references cited therein.
15. (d) Jones, R. C. F.; Patel, P.; Hirst, S. C.; Smallridge, M. J. Tetrahedron 1998, 54, 6191; and references cited therein.
16. (a) Jones, R. C. F.; Patel, P.; Hirst, S. C. Tetrahedron Lett. 1989, 30, 5361.
17. (b) Zhang, J.-H.; Wang, M.-X.; Huang, Z.-T. Tetrahedron Lett. 1998, 39, 9237.
18. (c) Zhang, J.-H.; Wang, M.-X.; Huang, Z.-T. J. Chem. Soc., Perkin Trans. 1 1999, 2087.
19. Jones, R. C. F.; Patel, P.; Hirst, S. C.; Turne, I. Tetrahedron 1997, 53, 11781.
20. Zhang, J.-H.; Wang, M.-X.; Huang, Z.-T. J. Chem. Soc., Perkin Trans. 1 1999, 321.
21. (a) Gante, J.; Mohr, G. Chem. Ber. 1975, 108, 174.
22. (b) Gompper, R.; Toepfl, W. Chem. Ber. 1962, 95, 2871.
23. (c) Yokoyama, M.; Tohnishi, M.; Kurihara, A.; Imamoto, T. Chem. Lett. 1982, 1933.
24. (d) Seshadri, S.; Sanghavi, N. M.; Naik, R. V.; Tawate, S. R.; Trivedi, M. N.; Fruitwala, M. A. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1993, 32, 688.
25. (e) Schwesinger, R.; Missfeldt, M.; Peters, K.; von Schnering, H. G. Angew. Chem. 1987, 99, 1210.
26. (f) Cheng, Y.; Wang, M.-X.; Gan, W.-X.; Huang, Z.-T. Synth. Commun. 1996, 26, 475.
27. (g) Yu, C.-Y.; Wang, L.-B.; Huang, Z.-T. Synth. Commun. 1996, 26, 2297.
28. (a) Middleton, W. J.; Engelhardt, V. A. J. Am. Chem. Soc. 1958, 80, 2788.
29. (b) Briel, D.; Dumke, S.; Wagner, G.; Olk, B. J. Chem. Res., Miniprint 1991, 1841.
30. (c) Tominaga, Y.; Yoshioka, N.; Kataoka, S. Heterocycles 1996, 43, 1597.
31. (d) Elgemeie, G. E. H.; Elghandour, A. H.; Elzanate, A. M.; Hussein, A. M. J. Chem. Res., Synop. 1997, 256.
32. Zhao, W.-G.; Liu, Z.-X.; Li, Z.-M.; Wang, B.-L. Synth. Commun. 2003, 33, 4229.
33. (a) Matsuda, Y.; Gotou, H.; Katou, K.; Matsumoto, H. Chem. Pharm. Bull. 1989, 37, 1188.
34. (b) Ram, V. J.; Srivastava, P.; Agarwal, N. J. Chem. Res., Synop. 2001, 421.
35. Reid, W.; Aboul-Fetouh, S. Tetrahedron 1988, 44, 7155.
36. 4OS: C, 63.88; H, 5.36; N, 16.56.
37. The crystal structure of 4a has been deposited at the Cambridge Crystallographic Data Centre and allocated the deposition number: CCDC 633314.