A domino annulation reaction under Willgerodt-Kindler conditions

Journal of Organic Chemistry

Volumn 73, Issue 12, 2008, Pages 4644-4649

  Kadzimirsz, Daniel ^a   Kramer, Daniel ^a   Sripanom, Lertnarong ^a   Oppel, Iris M ^a   Rodziewicz, Pawel ^a   Doltsinis, Nikos L ^a,b   Dyker, Gerald ^a  

^a RUHR UNIVERSITY BOCHUM   (Germany)

^b KING'S COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CHEMICAL REACTIONS; SULFUR COMPOUNDS; THIOPHENE;

(E ,3E) PROCESS; (I ,J) CONDITIONS; AMERICAN CHEMICAL SOCIETY (ACS); ANNULATION REACTIONS; CHEMICAL EQUATIONS; NUCLEOPHILIC AROMATIC SUBSTITUTION (NAS); REDOX PROCESSING; SIDE CHAINS;

AROMATIC COMPOUNDS;

2 BUTANONE; AROMATIC COMPOUND; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ANNULATION REACTION; ARTICLE; BIOTRANSFORMATION; CARBON NUCLEAR MAGNETIC RESONANCE; CRYSTAL STRUCTURE; DENSITY FUNCTIONAL THEORY; HECK REACTION; HYDROGEN BOND; OXIDATION REDUCTION REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 45249110670     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8005705     Document Type: Article

References (31)

1. (a) Willgerodt, C. Ber. Dtsch. Chem. Ges. 1888, 21, 534-536.
2. (b) Kindler, K. Liebigs Ann. Chem 1923, 431, 187-207.
3. Handbook of C-H Transfomations; Dyker, G., Ed.; Wiley-VCH: Weinheim, Germany, 2005.
4. Dyker, G.; Kadzimirsz, D. Eur. J. Org. Chem. 2003, 3167-3172.
5. Solovyev, A. Y.; Androsov, D. A.; Neckers, D. C. J. Org. Chem. 2007, 72, 3122-3124.
6. Kadzimirsz, D. Ph.D. Thesis, Bochum, 2003.
7. (a) Audoux, J.; Achelle, S.; Turck, A.; Marsais, F.; Ple, N. J. Heterocycl. Chem. 2006, 43, 1497-1503.
8. (b) Xu, Y.; Qu, B.; Qian, X.; Li, Y. Bioorg. Med. Chem. Lett. 2005, 15, 1139-1142.
9. (a) Dyker, G.; Thöne, A. J. Prakt. Chem. 1999, 341, 138-141.
10. (b) Dyker, G.; Grundt, P.; Markwitz, H.; Henkel, G. J. Org. Chem. 1998, 63, 6043-6047, and references cited therein.
11. (a) Asinger, F.; Saus, A.; Mayer, A. Monatsh. Chem. 1967, 98, 825-836.
12. (b) Xu, Y.; Qu, B.; Qian, X.; Li, Y. Bioorg. Med. Chem. Lett. 2005, 15, 1139-1142.
13. -3.
14. Schluecker, S.; Singh, R. K.; Asthana, B. P.; Popp, J.; Kiefer, W. J. Phys. Chem. A 2001, 105, 9983-9989.
15. Mayer, R.; Viola, H.; Reichert, J.; Krause, W. J. Prakt. Chem. 1978, 320, 313-323.
16. (a) Darabi, H. R.; Aghapoor, K. European Symposium on Organic Chemistry, 13th ed.; Cavtat-Dubrovnik, Croatia, 2003, 25-28.
17. (b) Kanyonyo, M. R.; Ucar, H.; Isa, M.; Carato, P.; Lesieut, D.; Renard, P.; Poupaert, J. H. Bull. Soc. Chim. Belg. 1996, 105, 17-22.
18. (c) DeTar, D. F.; Carmack, M. J. Am. Chem. Soc. 1946, 68, 2025-2029.
19. (d) King, J. A.; McMillan, F. H. J. Am. Chem. Soc. 1947, 69, 1207-1208.
20. (e) Carmack, M. J. Heterocycl. Chem. 1989, 26, 1319-1323.
21. (f) Asinger, F.; Saus, A.; Mayer, A. Monatsh. Chem. 1967, 98, 825-836.
22. (a) Heyde, C.; Zug, I.; Hartmann, H. Eur. J. Org. Chem. 2000, 3273-3278.
23. (b) Skramstad, J.; Chaudhry, M. S.; Garvang, A. Acta Chem. Scand. 1984, B38, 509-511.
24. (c) Fjeldstad, P. E.; Heim, K. Acta Chem. Scand. 1976, B30, 375-376.
25. Hoppe, H.; Hartke, K. Arch. Pharm. 1975, 308, 526-541.
26. Hutter, J., CPMD; see www.cpmd.org.
27. Vanderbilt, D. Phys. Rev. B 1990, 41, 7892-7895.
28. Becke, A. D.; Edgecombe, K. E. J. Chem. Phys. 1990, 92, 5397-5403.
29. Rousseau, R.; Marx, D. Chem. - Eur. J. 2000, 6, 2982-2993.
30. Goedecker, S.; Teter, M.; Hutter, J. Phys. Rev. B 1996, 54, 1703-1710.
31. Hartwigsen, C.; Goedecker, S.; Hutter, J. Phys. Rev. B 1998, 58, 3641-3662.