One-pot synthesis of furo[2,3-h]quinoline and furo[2,3-h]isoquinoline derivatives using Fischer carbene complex

Tetrahedron Letters

Volumn 52, Issue 2, 2011, Pages 251-253

  Roy, Priyabrata ^a   Ghorai, Binay K ^a  

^a INDIAN INSTITUTE OF ENGINEERING SCIENCE AND TECHNOLOGY   (India)

Author keywords

Benzannulation; Carbene complex; Furo 2,3 h isoquinoline; Furo 2,3 h quinoline

Indexed keywords

BENZENE; CARBENE; FURAN; FURO[2,3 H]ISOQUINOLINE DERIVATIVE; FURO[2,3 H]QUINOLINE DERIVATIVE; PYRIDINE; QUINOLINE DERIVATIVE; TRIPHENYLPHOSPHINE; UNCLASSIFIED DRUG;

ARTICLE; ONE POT SYNTHESIS;

EID: 78649981495     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.11.044     Document Type: Article

References (16)

1. A.E.A. Porter A.R. Katritzky, C.W. Rees, Comprehensive Heterocyclic Chemistry: the Structure, Reactions, Synthesis, and Uses of Heterocyclic Compounds 1984 Pergamon Press Oxford, UK 157 197
2. A. Chilin, C. Marzano, F. Baccichetti, M. Simonato, and A. Guiotto Bioorg. Med. Chem. 11 2003 1311 1318
3. C. Marzano, A. Chilin, F. Baccichetti, F. Bettio, A. Guiotto, G. Miolo, and F. Bordin Eur. J. Med. Chem. 39 2004 411 419
4. J. Kohno, H. Hiramatsu, M. Nishio, M. Sakurai, T. Okuda, and S. Komatsubara Tetrahedron 55 1999 11247 11252
5. G.J. Slack, E. Puniani, J.C. Frisvad, R.A. Samson, and J.D. Miller Mycol. Res. 113 2009 480 490
6. L. Xie, X. Qian, J. Cui, Y. Xiao, K. Wang, P. Wu, and L. Cong Bioorg. Med. Chem. 16 2008 8713 8718
7. K.H. Dötz, and P. Tomuschat Chem. Soc. Rev. 28 1999 187 198
8. Bromoaldehydes 6 were prepared by the regioselective ortho-lithiation of 2-bromopyridine/3-bromopyridine followed by quenching with DMF, according to a literature procedure. A. Numata, Y. Kondo, and T. Sakamoto Synthesis 1999 306 311
9. For benzannulation through CO insertion, see: Y. Zhang, D. Candelaria, and J.W. Herndon Tetrahedron Lett. 46 2005 2211 2214
10. CO insertion is a minor reaction pathway during the coupling reaction of ethynylstyrene derivatives with carbene complexes: T.J. Jackson, and J.W. Herndon Tetrahedron 57 2001 3859 3868
11. L. Zhang, and J.W. Herndon Organometallics 23 2004 1231 1235
12. J. Zhang, Y. Zhang, W.F.K. Schnatter, and J.W. Herndon Organometallics 25 2006 1279 1284
13. +: 242.0817; found: 242.0813.
14. M.E. Bos, W.D. Wulff, R.A. Miller, S. Chamberlin, and T.A. Brandvold J. Am. Chem. Soc. 113 1991 9293 9319
15. R. Li, L. Zhang, A. Camacho-Davila, and J.W. Herndon Tetrahedron Lett. 46 2005 5117 5120
16. K. Maeyama, and N. Iwasawa J. Org. Chem. 64 1999 1344 1346