3-Hydroxy-3-methyl-2-butanone 1 reacted with ethyl cyanocetate in 2 in the presence of sodium ethoxide under focused microwave irradiations to afford 3-cyano-4,5,5-trimethyl-2-(5H)-furanone 3. Furanone 3 then condensed with aromatic or heteroaromatic aldehydes 4a–h to produce 3-cyano-4-(trans-aryl-vinyl)-5,5-dimethyl-2-(5H)-furanones 5a–h in high overall yields (71–88%).
(a) RupprechtJ.K., HuiY.-H, and McLaughlinJ. L., J. Nat. Prod., 1990, 53, 237–258
5.
GuZ.M., ZhaoG. X., OberliesN. H., ZengL., and McLaughlinJ. L. in Recent Adv. Phytochem., ed., ArnasonJ.T., MataR., and RomeoJ. R., Plenum Press, New York, 1995, Vol. 29, pp 249–310
6.
ZengL., YeQ., OberliesN. H., ShiG., GuZ.-M, HeK., and McLaughlinJ. L., J. Nat. Prod. Rep., 1996, 13, 275–306.
7.
(a) RaoY.S., Chem. Rev., 1964, 64, 353–388
8.
RaoY.S., Chem. Rev., 1976, 76, 625–694
9.
AvetisyanA.A., and DangyanM. T., Russ. Chem. Rev., 1977, 46, 643–656.
10.
VilleminD., and LiaoL., Tetrahdreon Lett., 1996, 37, 8733–8734.
11.
For a review on focused microwave action: A Loupy, PetitA., HamelinA., TexierBoulletJ., JacquaultF., MatheP.D. Synthesis, 1998, 1213–1234.
12.
PerjéssyA., AvetisyanA. A., AknazaryanA. A., and MelikyanG. S., Collect. Czech. Chem. Commun., 1989, 54, 1666–74.
13.
GordanA.J., and FordR. A., The Chemist's Companion – A Handbook of Practical Data, Techniques, and References, John Wiley, New York, 1972, p. 275.
14.
Although results were obtained with a cavity EO13 of MES described previously,9 we recently obtained similar results with a Prolabo Synthewave 402 and with a tube of internal diameter of 10 mm as reactor.
15.
VilleminD., and MartinB., Synth. Commun., 1995, 25, 2319–2326.