Synthesis of Two Novel Ring Systems via Photocyclization: Thieno[2′,3′:4,5]thieno[2,3-c][1,10]Phenanthroline and Thieno[3′,2′:4,5]thieno[2,3-c][1,10]Phenanthroline

Journal of Heterocyclic Chemistry

Volumn 33, Issue 1, 1996, Pages 119-122

  Halverson, Aileen Pfleider ^a   Castle, Lyle W ^a   Castle, Raymond N ^b  

^a IDAHO STATE UNIVERSITY   (United States)

^b UNIVERSITY OF SOUTH FLORIDA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0346586520     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570330121     Document Type: Article

References (23)

1. [1a] Part 1: S. L. Castle, J.-K. Luo, H Kudo and R. N. Castle, J. Heterocyclic Chem., 25, 1363 (1988);
2. [b] Part 2: J.-K. Luo and R. N. Castle, J. Heterocyclic Chem., 27, 1031 (1990);
3. [c] Part 3: M. J. Musmar and R. N. Castle, J. Heterocyclic Chem., 28, 203 (1991);
4. [d] Part 4: J.-K. Luo, A. S. Zektzer and R. N. Castle, J. Heterocyclic Chem., 28, 737 (1991);
5. [e] Part 5: J.-K. Luo and R. N. Castle, J. Heterocyclic Chem., 28, 1825 (1991);
6. [f] Part 6: R. N. Castle, S. Pakray and G. E. Martin, J. Heterocyclic Chem., 28, 1997 (1991);
7. [g] Part 7: K. Sasaki and R. N. Castle, J. Heterocyclic Chem., 29, 963 (1992);
8. [h] Part 8: K. Sasaki and R. N. Castle, J. Heterocyclic Chem., 29, 1613 (1992);
9. [i] Part 9: Ch. Camoutsis and R. N. Castle, J. Heterocyclic Chem., 30, 153 (1993);
10. [j] Part 10: M. J Musmar, A. S. Zektzer, R. N. Castle and N. K. Dalley, J. Heterocyclic Chem., 30, 487 (1993);
11. [k] Part 11: J.-K Luo, A. S. Zektzer, R. N. Castle, R. C. Crouch, J. P. Shockcor and G. E. Martin, J. Heterocyclic Chem., 30, 453 (1993);
12. [I] Part 12: J.-K. Luo, S. L. Castle and R. N. Castle, J. Heterocyclic Chem., 30, 653 (1993);
13. [m] Part 13: J.-K. Luo and R. N. Castle, J. Heterocyclic Chem., 30, 1167 (1993);
14. [n] Part 14: M. J. Musmar and R. N. Castle, J. Heterocyclic Chem., 31, 553 (1994);
15. [o] Part 15: J.-K. Luo, R. F. Federspiel and R. N, Castle, J. Heterocyclic Chem., 32, 317 (1995);
16. [p] Part 16: J.-K. Luo, R. F. Federspiel and R. N. Castle, J. Heterocyclic Chem., 32, 659 (1995).
17. W. B. Wright Jr., J. Heterocyclic Chem., 9, 879 (1972).
18. H. C. Brown and S. Krishnamurthy, J. Org. Chem., 34, 3918 (1969).
19. J. E. Huheey, Inorganic Chemistry: Principles of Structure and Reactivity, 3rd Ed, Harper & Row, NY, 1983, p 654.
20. [5a] K. Nagayama, A. Kumar, K Wuthrich and R. R. Ernst, J. Magn. Reson., 40, 321 (1980);
21. [b] G. Bodenhausen and R. R. Ernst, J. Am. Chem. Soc., 104, 1304 (1982);
22. [c] A. Bax and R. Freeman, J. Magn. Reson., 44, 542 (1981).
23. The synthesis of 1 according to the procedure in reference [2] also produced 3,5-dichlorothieno[3,2-b]thiophene-2-carbonyl chloride as a side-product. Instead of separating the two products, both were carried through the sequence in Scheme 1. The penultimate products were 4 and its 6,9-dichloro analog.