Formation of 1,10-disubstituted benzo[c]cinnolines. Synthesis and molecular structure of 1-amino-10-propylthiobenzo[c]cinnoline and cyclization to 4-propylcinnolino[5,4,3][c,d,e][1,2]benzothiazine

Journal of Organic Chemistry

Volumn 65, Issue 20, 2000, Pages 6388-6397

  Benin, Vladimir ^a   Kaszynski, Piotr ^a   Pink, Maren ^b   Young Jr , Victor G ^b  

^a VANDERBILT UNIVERSITY   (United States)

^b University of Minnesota ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 AMINO 10 PROPY[THIOBENZO[C]CINNOLINE; 4 PROPYLCINNOLINO[5,4,3][C,D,E][1,2]BENZOTHIAZINE; BENZENE DERIVATIVE; BENZOTHIAZINE DERIVATIVE; TRINITROBIPHENYL; UNCLASSIFIED DRUG;

ABSORPTION SPECTROPHOTOMETRY; ARTICLE; CALCULATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CRYSTAL STRUCTURE; CYCLIZATION; OXIDATION; REACTION ANALYSIS; REDUCTION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0034613332     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0002691     Document Type: Article

References (40)

1. Barton, J. W. In Advances in Heterocyclic Chemistry, Katritzky, A. R., Boulton, A. J., Eds.; Academic Press: New York, 1979; Vol. 24; pp 151-185, and references therein.
2. Buntrock, R. E.; Taylor, E. C. Chem. Rev. 1968, 68, 209-227, and references therein.
3. Stetter, H.; Schwarz, M. Chem. Ber. 1957, 90, 1349.
4. Castle, R. N.; Guither, W. D.; Hilbert, P.; Kempter, F. E.; Patel, N. R. J. Heterocycl. Chem. 1969, 6, 533.
5. Kiliç, E.; Tüzün, C. Synth. Commun. 1992, 22, 545, and references therein.
6. Benin, V.; Kaszynski, P. J. Org. Chem., in press. See also: Kaszynski, P. In Magnetic Properties of Organic Materials; Lahti, P. M., Ed.; Marcel Dekker: New York, 1999; pp 305-324.
7. Benin, V.; Kaszynski, P. J. Org. Chem., in press. See also: Kaszynski, P. In Magnetic Properties of Organic Materials; Lahti, P. M., Ed.; Marcel Dekker: New York, 1999; pp 305-324.
8. Sako, S. Bull. Chem. Soc. Jpn. 1934, 9, 393.
9. Wittig, G.; Stichnoth, O. Chem. Ber. 1935, 68, 928.
10. Wilcox, C. F.; Lassila, K. R.; Kang, S. J. Org. Chem. 1988, 53, 4333.
11. Braithwaite, R. S. W.; Holt, P. F. J. Chem. Soc. 1959, 3025.
12. Shepherd, M. K. J. Chem. Soc., Perkin Trans. 1 1994, 1055.
13. MacBride, J. A. H.; Wright, P. M. Tetrahedron Lett. 1981, 22, 4545.
14. Arcos, J. C.; Arcos, M.; Miller, J. A. J. Org. Chem. 1956, 21, 651.
15. Barton, J. W.; Rowe, D. J. Tetrahedron Lett. 1983, 24, 299.
16. Barton, J. W.; Shepherd, M. K. Tetrahedron Lett. 1984, 25, 4967.
17. Sienkowska, M.; Benin, V.; Kaszynski, P. Tetrahedron 2000, 56, 165.
18. Badger, G. M.; Seidler, J. H.; Thomson, B. J. Chem. Soc. 1951, 3207.
19. Smith, W. B. J. Heterocycl. Chem. 1987, 24, 745.
20. Ross, S. D.; Kuntz, I. J. Am. Chem. Soc. 1952, 74, 1297.
21. Muth, C. W.; Abraham, N.; Linfield, M. L.; Wotring, R. B.; Pacofsky, E. A. J. Org. Chem. 1960, 25, 736.
22. Paradisi, C.; González-Trueba, G.; Scorrano, G. Tetrahedron Lett. 1993, 34, 877.
23. Bergeron, R. J.; McManis, J. J. J. Org. Chem. 1988, 53, 3108.
24. Barton, J. W.; Cockett, M. A. J. Chem. Soc. 1962, 2454.
25. Shimizu, H.; Ikedo, K.; Hamada, K.; Ozawa, M.; Matsumoto, H.; Kamata, K.; Nakamura, H.; Ji, M.; Kataoka, T.; Hori, M. J. Chem. Soc., Perkin Trans. 1 1991, 1733.
26. 2) = 0.0484 (for all data, 3617 reflections). For details see the Supporting Information.
27. Whittleton, S. N.; Dunitz, J. D. Acta Crystallogr. 1982, B38, 2052 and 2053.
28. Rowland, R. S.; Taylor, R. J. Phys. Chem. 1996, 100, 7384.
29. van der Meer, H. Acta Crystallogr. 1972, B28, 367.
30. Chebli, C.; Brisse, F. Acta Crystallogr. 1995, C51, 1164.
31. Badger, G. M.; Walker, I. S. J. Chem. Soc. 1956, 122.
32. Lippert, E.; Voss, W. Z. Physik. Chem. (Frankfurt), 1962, 31, 321.
33. Ohe, K.; Sakae, U.; Sugita, N.; Masuda, H.; Taga, T. J. Org. Chem. 1989, 54, 4169.
34. Rosenblatt, D. H.; Burrows, E. P. In Supplement F: The Chemistry of Amino, Nitroso and Nitro Compounds and Their Derivatives; Patai, S., Ed.; Wiley: New York, 1982; Vol. 2; pp 1085-1149, and references therein.
35. Hedayatullah, M. Bull. Soc. Chim. Fr. 1972, 2957.
36. Horner, L.; Dehnert, J. Chem. Ber. 1963, 96, 786.
37. Varvoglis, A. Chem. Soc. Rev. 1981, 10, 377.
38. Wicha, J.; Zarecki, A.; Kocór, M. Tetrahedron Lett. 1973, 3635.
39. Gaussian 94, Revision E.1: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian, Inc., Pittsburgh, PA, 1995. Gaussian 94, Revision E.1, Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.;Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian, Inc., Pittsburgh, PA, 1995.
40. Gaussian 94, Revision E.1: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian, Inc., Pittsburgh, PA, 1995. Gaussian 94, Revision E.1, Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.;Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian, Inc., Pittsburgh, PA, 1995.