Application of directed metalation in synthesis. Part 8: Interesting example of chemoselectivity in the synthesis of thioaurones and hydroxy ketones and a novel anionic ortho-Fries rearrangement used as a tool in the synthesis of thienopyranones and thiafluorenones

Tetrahedron

Volumn 61, Issue 38, 2005, Pages 9007-9017

  Pradhan, Tarun Kanti ^a   De, Asish ^a   Mortier, Jacques ^b  

^a DEPARTMENT OF MATERIALS SCIENCE   (India)

^b UNIVERSITÉ DU MAINE   (France)

Author keywords

Anionic ortho Fries rearrangement; Benzothienopyranone; Chalcone; Chemoselectivity; Directed metalation; Thioaurones

Indexed keywords

ALKYL GROUP; AMIDE; CHALCONE DERIVATIVE; KETONE DERIVATIVE; NAPHTHALENE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRAN DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL REACTION; GAS CHROMATOGRAPHY; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 23944452023     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.07.050     Document Type: Article

References (17)

1. Part 7. T.K. Pradhan, and A. De Tetrahedron Lett. 46 2005 1493
2. C. Mukherjee, and A. De Synlett 2002 325
3. C. Mukherjee, S. Kamila, and A. De Tetrahedron 59 2003 4767
4. T.K. Pradhan, S.C. Ghosh, and A. De ARKIVOC 2003 158 Part (ix)
5. T.K. Pradhan, and A. De Heterocycles 65 2005 1491
6. S. Kamila, C. Mukherjee, S.S. Mondal, and A. De Tetrahedron 59 2003 1339
7. V. Snieckus Chem. Rev. 90 1990 879
8. J.B. Wright, and H.G. Johnson J. Med. Chem. 16 1973 861
9. H. Cairns, C. Fitzmaurice, D. Hunter, P.B. Johnson, J. King, T.B. Lee, G.H. Lord, R. Minshull, and J.S.G. Cox J. Med. Chem. 15 1972 583
10. C.J. Falliers J. Allergy 47 1971 298
11. For various application of thioaurones. M. Ahlheim, M. Barzoukas, P.V. Bedworth, M. Blanchard-Desce, A. Fort, Z.-Y. Hu, S.R. Marder, J.W. Perry, C. Runser, B. Staehlin, and B. Zysset Science 271 1996 335
12. W. Steinle, and K. Rück-Braun Org. Lett. 5 2002 141
13. M.G. Cabbidu, S. Cabbidu, E. Cadoni, S. de Montis, C. Fattuoni, S. Melis, and M. Usai Synthesis 2002 875
14. M.P. Sibi, and V. Snieckus J. Org. Chem. 48 1983 1935
15. A. Mustafa, S. Mohamed, and A.D. Zayed J. Am. Chem. Soc. 78 1956 6174
16. A. Mustafa, W. Asker, O.H. Hishmat, M.I. Ali, A.-K.E. Mansour, N.M. Abed, K.M.A. Khalil, and S.M. Samy Tetrahedron 21 1965 849
17. S. Smiles, and L.W. McClelland J. Chem. Soc. 119 1921 1810