Abstract
3-(Iodomethyl)coumarins and 3-(chloromethyl)coumarins, obtained chemoselectively via Baylis–Hillman reactions of salicylaldehyde derivatives with t-butyl acrylate, can be reacted with triethyl phosphite to afford regioisomeric Michaelis-Arbuzov products. Under nitrogen, the 3-(iodomethyl)coumarins undergo direct displacement of iodide to afford the expected 1′-phosphonated derivatives. The reactions with 3-(chloromethyl)coumarins in air, however, proceed with overall allylic rearrangement to afford the regioisomeric 3-methyl-4-phosphonated derivatives.
Keywords
References
1.
Ghate M.
,
Manohar D.
,
Kulkarni V.
,
Shobha R.
, and
Kattimani S. Y.
, Eur J. Med. Chem. , 2003 , 38 , 297 .
2.
Kontogiorgis C.
, and
Hadjipavlou-Litina D.
, J. Enzyme Inhib. Med. Chem. , 2003 , 18 , 63 .
3.
Mouri T.
,
Yano T.
,
Kochi S.
,
Ando T.
, and
Hori M.
, J. Pestic. Sci. , 2005 , 30 , 209 .
4.
Spino C.
,
Dodier M.
, and
Sotheeswaran S.
, Bioorg. Med. Chem. , 1998 , 8 , 3475 .
5.
Tummino P.J.
,
Ferguson D.
, and
Hupe D.
, Biochem. Biophys. Res. Commun. , 1994 , 201 , 290 . (Chem. Abstr. 1994,121:73068.)
6.
Thaisrivongs S.
,
Tomich P. K.
,
Watenpaugh K. D.
,
Chong K. H. W.
,
Howe K.
,
Yang C.
,
Strohbach J.
,
Tureer S.
,
McGrath J.
,
Bohanon M.
,
Lynn J.
,
Mulichak A.
,
Spinelli P.
,
Hinshaw R.
,
Pagano P.
,
Moon J.
,
Ruwart M.
,
Wilkinson K.
,
Rush B.
,
Zipp G.
,
Dalga R.
,
Schwende F.
,
Howard G. P. G.
,
Toth L.
,
Zhao Z.
,
Koeplinger K.
,
Kakuk T.
,
Cole S.
,
Zaya R.
,
Piper R.
, and
Jeffrey P.
, J. Med. Chem. , 1994 , 37 , 3200 .
7.
Singh I.P.
,
Bharate S. B.
, and
Bhutani K. K.
, Curr. Sci. , 2005 , 89 , 2 .
8.
Lima O.A.
, and
Polonskwi J.
, Phytochemistry , 1973 , 12 , 913 .
9.
Dean F.M.
, Naturally occurring oxygen ring compounds , Butterworths , London , 1963 , p. 337 .
10.
Maheswar M.
,
Vidavalur S.
,
Guri L.
,
Vasantha D.
,
Yerra K. R.
, and
Rao C. V.
, J. Mol. Catal. , 2006 , 255 , 49 .
11.
Vilar S.
,
Quezada E.
,
Santana L.
,
Uriarte E.
,
Fraiz Y. N.
,
Alcaide C.
,
Cano E.
, and
Orallo F.
, Bioorg. Med. Chem. Lett , 2006 , 16 , 257 .
12.
Heravi M.M.
,
Hekmatshoar R.
, and
Emamgholizadeh M.
, Phosphorus, Sulfur Silicon Relat Elem. , 2004 , 179 , 1893 .
13.
Bogdal D.
, J. Chem. Res (S). , 1998 , 468 .
14.
Familoni O.B.
,
Klaas P. J.
,
Lobb K. A.
,
Pakade V. E.
, and
Kaye P. T.
, Org. Biomol. Chem. , 2006 , 4 , 3960 .
15.
Kaye P.T.
, S. Afr. J. Sci. , 2004 , 100 , 545 .
16.
Kaye P.T.
, and
Musa M. A.
, Synth. Commun. , 2003 , 33 (10 ), 1755
17.
Kaye P.T.
, and
Musa M. A.
, Synthesis , 2002 , 2701 .
18.
Kaye P.T.
,
Musa M. A.
, and
Nocanda X. W.
, Synthesis , 2003 , 531 .
19.
Kaye P.T.
,
Musa M. A.
,
Nchinda AT
., and
Nocanda X. W.
, Synth. Commun. , 2004 , 34 , 2575 .
20.
March J.
, Advanced organic chemistry: reactions, mechanisms and structure , 4th edn, Wiley Interscience , New York , 1992 , p. 959 .
21.
Kaye P.T.
, and
Musa M. A.
, Synth. Commun. , 2004 , 34 , 3409 .
22.
Cartwright G.A.
, and
McNab H. J.
, J. Chem. Res. (S) , 1997 , 296 .