Novel synthesis of cinnolines and 1-aminoindolines via Cu-catalyzed intramolecular N-arylation of hydrazines and hydrazones prepared from 3-haloaryl-3-hydroxy-2-diazopropanoates

Journal of Organic Chemistry

Volumn 73, Issue 16, 2008, Pages 6363-6368

  Hasegawa, Kazuya ^a   Kimura, Naoki ^a   Arai, Shigeru ^a   Nishida, Atsushi ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL EQUATIONS; FACILE ACCESS; HYDRAZONES; N-ARYLATION; NITROGEN HETEROCYCLE; ONE-POT; PHASE-TRANSFER CATALYSIS; UV-SPECTRUM;

AROMATIC COMPOUNDS; CARBOXYLATION; CATALYSIS; CHEMICAL REACTIONS; COPPER; COPPER ALLOYS; HYDRAZINE; NITROGEN; NONMETALS; SYNTHESIS (CHEMICAL); ULTRAVIOLET SPECTROSCOPY;

REACTION KINETICS;

1 AMINOINDOLINE; 3 HALOARYL 3 HYDROXY 2 DIAZOPROPANOATE; CINNOLINE; COPPER; HETEROCYCLIC COMPOUND; HYDRAZINE; HYDRAZONE DERIVATIVE; INDOLE DERIVATIVE; NITROGEN; PROPANE;

ARTICLE; ARYLATION; CATALYSIS; CYCLIZATION; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

AMINES; CATALYSIS; COPPER; HETEROCYCLIC COMPOUNDS, 2-RING; HYDRAZINES; HYDRAZONES; INDOLES; PROPIONATES; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 50149122391     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8010864     Document Type: Article

References (34)

1. (a) Wieslawa, L.; Andrzej, S. Arch. Pharm. 2007, 340, 65-80.
2. (b) Cignarella, G.; Sanna, P. J. Med. Chem. 1981, 24, 1003-1006, and references therein
3. For isolation of schizocommunin, see: (c) Hosoe, T.; Nozawa, K.; Kawahara, N.; Fukushima, K.; Nishimura, K.; Miyaji, M.; Kawai, K. Mycopathologia 1999, 146, 9-12.
4. Turck, A.; Plé, N.; Tallon, V.; Quéguiner, G. Tetrahedron 1995, 51, 13045-13060, and references therein.
5. Chapoulaud, V. G.; Plé, N.; Turck, A.; Quéguiner, G. Tetrahedron 2000, 56, 5499-5507.
6. (a) von Richter, V. Chem. Ber. 1883, 16, 677-683.
7. (b) Li, J.-J.; Cook, J. M. Name Reactions in Heterocyclic Chemstry; Wiley-Interscience: Hoboken, NJ, 2005; pp 540-543.
8. (c) Vasilevsky, S. F.; Tretyakov, E. V. Liebigs Ann. 1995, 775-779.
9. (d) Schofield, K.; Swain, T. J. Chem. Soc. 1949, 2393-2399.
10. Haley and co-workers reported thermal cyclization of 2- ethynylphenyltriazenes; see: (e) Kimball., D. B.; Hayes, A. G.; Haley, M. M. Org. Lett. 2000, 2, 3825-3827.
11. (a) Barber, H. J.; Washbourn, K.; Wragg, W. R.; Lunt, E. J. Chem. Soc. 1961, 2828-2843.
12. (b) Shoup, R. R.; Castle, R. N. J. Heterocycl. Chem. 1965, 2, 63-66.
13. (c) Al-Awadi, N. A.; Elnagdi, M. H.; Ibrahim, Y. A.; Kaul, K.; Kumar, A. Tetrahedron 2001, 57, 1609-1614.
14. (d) Sereni, L.; Tató, M.; Sola, F.; Brill, W. K.-D. Tetrahedron 2004, 60, 8561-8577.
15. (a) Miyamoto, T.; Matsumoto, J. Chem. Pharm. Bull. 1988, 36, 1321-1327.
16. (b) Sandison, A. A.; Tennant, G. J. Chem. Soc., Chem. Commun. 1974, 752-753.
17. (c) Ames, D. E.; Leung, O. T.; Singh, A. G. Synthesis 1983, 52-53.
18. For reviews of α-diazocarbonyl compounds, see: (a) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; Wiley Interscience: New York, 1998.
19. (b) Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091-1160.
20. (c) Zhao, Y.; Wang, J. Synlett 2005, 2886-2892.
21. For recent application of indole synthesis from N-arylhydrazone prepared from α-diazoesters, see: (d) Yasui, E.; Wada, M.; Takamura, N. Tetrahedron Lett. 2006, 47, 743-746.
22. (a) Arai, S.; Hasegawa, K.; Nishida, A. Tetrahedron Lett. 2004, 45, 1023-1026; 2005, 46, 6171.
23. (b) Hasegawa, K.; Arai, S.; Nishida, A. Tetrahedron 2006, 62, 1390-1401.
24. (a) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 10251-10263.
25. (b) Prim, D.; Campagne, J.; Joseph, D.; Andrioletti, B. Tetrahedron 2002, 58, 2041-2075.
26. (a) Ley., S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400-5449.
27. (b) Yamada, K.; Kubo, T.; Tokuyama. H.; Fukuyama, T. Synlett 2002, 231-234.
28. (c) Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421-7428.
29. Sakamoto reported that both E- and Z-isomer hydrazones successfully cyclized to give indazole via intramolecular N-arylation under Pd catalysis; see: Inamoto, K.; Katsuno, M.; Yoshino, T.; Suzuki, I.; Hiroya, K.; Sakamoto, T. Chem. Lett. 2004, 33, 1026-1027. Our result using the Z-isomer is described in Supporting Information.
30. Holzer, W.; Eller, G. A.; Schönberger, S. Heterocycles 2008, 75, 77-86.
31. Stanton, J. L.; Ackerman, M. H. J. Med. Chem. 1983, 26, 986-989.
32. Collot, V.; Schmitt, M.; Marwah, P.; Bourguignon, J. Heterocycles 1999, 51, 2823-2847.
33. The stereochemistry of 17a,b was determined by conversion to tert-butyl 2-(N-benzoylhydrazino)-3-phenyl-3-(tert-butyldimethylsilyloxy)propionate by dehalogenation (s-BuLi/THF,- 78°C, 1 h); see ref 8b.
34. Burk, M. J.; Feaster, J. E. J. Am. Chem. Soc. 1992, 114, 6266-6267.