Abstract
Reaction of a series of chromone-3-carbaldehydes with methyl vinyl ketone under Baylis–Hillman conditions, using 3-hydroxyquinuclidine in chloroform or DABCO in 1-methyl-2-pyrrolidinone, affords unprecedented tricylic chromone derivatives which, depending on the conditions, may be accompanied by the normal Baylis–Hillman products or their respective tricyclic dimers.
References
1.
Gao F.
,
Bailes E.
,
Robertson D. L.
,
Chen Y.
,
Rodenburg C. M.
,
Michael S. F.
,
Cummins L. B.
,
Arthur L. O.
,
Peeters M.
,
Shaw G. M.
,
Sharp P. M.
, and
Hahn B. H.
, Nature , 1999 , 397 , 436 .
2.
Strauss J.H.
, and
Strauss E. G.
, Viruses and human disease , Academic Press , London , 2002 , pp. 196 , 197.
3.
Welker R.
,
Hohenberg H.
,
Tessmer U.
,
Huckhagel C.
, and
Kräusslich H.
, J. Virol , 2000 , 74 , 1168 .
4.
Strauss J.H.
, and
Strauss E. G.
, Viruses and human disease , Academic Press , London , 2002 , p. 49 .
5.
Wiegers K.
,
Rutter G.
,
Kottler H.
,
Tessmer U.
,
Hohenberg H.
, and
Kräusslich H. G.
, J. Virol. , 1998 , 72 , 2846 .
6.
Shehu-Xhigala M.
,
Kraeusslich H. G.
,
Pettit S.
,
Swanstrom R.
,
Lee J. Y.
,
Marshall J. A.
,
Crowe S. M.
, and
Mak J.
, J. Virol. , 2001 , 75 , 9156 .
7.
Molefe D.
, and
Kaye P. T.
, Synth. Commun. , in press.
8.
Kaye P.T.
,
Nchinda A. T.
,
Sabbagh L. V.
, and
Bacsa J.
, J. Chem. Res.(S) , 2003 , 111 ; J. Chem. Res. (M) , 2003, 0301.
9.
Kaye P.T.
,
Molefe D. M.
,
Nchinda A. T.
, and
Sabbagh L. V.
, J. Chem. Res. , 2004 , 303 .
10.
Nohara A.
,
Umetani T.
, and
Sanno Y.
, Tetrahedron , 1974 , 30 , 3353 .
11.
Molefe D.M.
, PhD thesis , Rhodes University , 2007 .
12.
Payne D.J.
,
Hueso-Rodriguez J. A.
,
Boyd H.
,
Concha N. O.
,
Janson C. A.
,
Gilpin M.
,
Bateson J. H.
,
Cheever C.
,
Niconovich N. L.
,
Pearson S.
,
Rittenhouse S.
,
Tew D.
,
Diez E.
,
Perez P.
,
De la Fuente J.
,
Rees M.
, and
Rivera-Sagredo A.
, Antimicrob. Agents Chemother , 2002 , 46 , 1880 . (Chem. Abstr. , 2002, 137 , 137439.)
13.
Kumagai K.
, and
Hosotani N.
, Patent application: WO 2003-JP567 20030122. (Chem. Abstr. , 2003 , 139 , 148558.)
14.
Ganto M.M.
, PhD thesis , Rhodes University , 2008 .
15.
Aggarwal V.K.
, and
Mereu A.
, J. Chem Soc., Chem. Commun. , 1999 , 2311 .
16.PC SPARTAN-pro , version 1.1, Wavefunction Inc. , Irvine , 1999 .