X-ray crystallographic studies of four monosubstituted thienopyridines. Comparison of experimental data with calculated or measured values for the parent compounds

Heterocyclic Communications

Volumn 5, Issue 4, 1999, Pages 311-318

  Klemm, LeRoy H ^a   Weakley, Timothy J R ^a   Yoon, Myungok ^a  

^a UNIVERSITY OF OREGON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0033421867     PISSN: 07930283     EISSN: None     Source Type: Journal    
DOI: 10.1515/HC.1999.5.4.311     Document Type: Article

References (26)

1. J. M. Barker, The Thienopyridines, in A. R. Katritzky and A. J. Boulton (Eds.), Advances in Heterocyclic Chemistry, Vol. 21, Academic Press, New York, 1977, pp. 65-118
2. L. H. Klemm, Recent Interrelationships in the Chemistries of Thienopyridines, Benzopyridines, and Benzothiophenes, in Trends in Heterocyclic Chemistry, Vol. 5, Research Trends, Trivandrum, India, 1997, pp. 37-55
3. L. H. Klemm, W. O. Johnson, and D. V. White, J. Heterocycl. Chem. 7, 463 (1970)
4. A. Helland and P. N. Skancke, Acta Chem. Scand. 26, 2601 (1972)
5. J. S. Webber and R. G. Woolley, J. Mol. Struct. (Theochem) 341, 181 (1995)
6. L. H. Klemm, C. E. Klopfenstein, R. Zell, D. R. McCoy, and R. A. Klemm, J. Org. Chem. 34, 347 (1969)
7. M. Farnier, S. Soth, and P. Fournari, Can. J. Chem. 54, 1066 (1976)
8. H. Nerenz, W. Grahn, and P. G. Jones, Acta Crystallogr., Sect. C, Cryst. Struct. Commun. 53, 787 (1997)
9. Determined on a Varian INOVA 300 MHz instrument
10. Suitable nmr data have already been reported for 1b
11. M. C. Burla, M. Camalli, G. Cascarano, C. Giacovazzo, G. Polidori, R. Spagna, and D. Viterbo, J. Appl. Crystallogr. 22, 389 (1989)
12. P. T. Beurskens, W. P. Bosman, H. M. Doesburg, R. O. Gould, T. E. M. Van der Hark, P. A. J. Prick, K. H. Noordik, G. Beurskens, V. Parthasarathi, H. J. Bruins Slot, R. C. Haltiwanger, M. Strumpel, and J. M. M. Smits, DIRDIF: Direct Methods for Difference Structures, Technical Report, Crystallography Lab., Toernooiveld, Netherlands, 1984
13. TeXsan software for single crystal structure analysis, version 1.7, Molecular Structures Corp., The Woodlands, TX, 1997
14. D. T. Cromer and J. T. Waber, in J. A. Ibers and W. T. Hamilton (Eds.), International Tables for X-ray Crystallography, Vol. IV, Kynoch Press, Birmingham, England, 1974, pp 71, 148
15. L. H. Klemm and J. N. Louris, J. Heterocycl. Chem. 21, 785 (1984)
16. L. H. Klemm and J. N. Louris, Heterocycl. Commun. 1, 375 (1995)
17. L. H. Klemm and J. N. Louris, Heterocycl. Commun. 2, 493 (1996)
18. L. H. Klemm and D. R. Muchiri, J. Heterocycl. Chem. 20, 213 (1983)
19. CH fall in the range of 167-188 Hz; longer-range CH coupling constants, in the range of 2-9 Hz
20. 13C nmr data on isoquinoline (21,22) and parent thienopyridines 1a-4a (15,16,23)
21. L. F. Johnson and W. C. Jankowski, Carbon-13 NMR Spectra, John Wiley, New York, 1972, spectrum 334
22. K. Tori and T. Nakagawa, J. Phys. Chem. 68, 3163 (1964)
23. L. H. Klemm and R. E. Merrill, unpublished data
24. L. H. Klemm, I. T. Barnish, and D. R. McCoy, J. Heterocycl. Chem. 14, 299 (1977)
25. L. H. Klemm and R. E. Merrill, J. Heterocycl. Chem. 11, 355 (1974)
26. c-3 for 4a + 1.143 times the ipso substituent chemical shift of the NHAc group in benzene, i.e. 123.8 = 121.4 + (1.143) (2.1). See ref. (16) and D. F. Ewing, Org. Magn. Reson. 12, 499 (1979)