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Synthesis 2003(8): 1286-1291
DOI: 10.1055/s-2003-39408
DOI: 10.1055/s-2003-39408
FEATUREARTICLE
© Georg Thieme Verlag Stuttgart ˙ New York
The Reactivity of 4-Hydroxycoumarin under Heterogeneous High-Intensity Sonochemical Conditions [1]
Further Information
Received
11 January 2003
Publication Date:
26 May 2003 (online)
Publication History
Publication Date:
26 May 2003 (online)
Abstract
High-intensity ultrasounds have been employed in the synthesis of 4-hydroxycoumarin derivatives, using mainly water as reaction medium. Marked improvements of reaction rates, chemoselectivity and product yields have been observed on comparing sonochemical with ordinary conditions. In the alkylation of a series of allyl and benzyl bromides a pathway switch occured to yield 3-alkyl-4-hydroxycoumarin derivatives.
Key words
sonochemistry - ultrasounds - 4-hydroxycoumarin - coumarin derivatives - chemoselectivity
- 1 Part XIII in the series, The Chemistry
of Coumarin Derivatives. For Part XII, see:
Cravotto G.Nano GM.Palmisano G.Pilati T.Tagliapietra S. J. Hetercycl. Chem. 2001, 38: 965 - 2
Stahmann A,Ikawa M, andLink KP. inventors; US Pat 2427578. ; Chem. Abstr. 1948, 42, P603h - 3
Murray RDH.Mendez J.Brown SA. The Natural Coumarins Wiley; Chichester, UK: 1982. - 4
Hinman JW.Hoeksema H.Caron EL.Jackson WG. J. Am. Chem. Soc. 1956, 78: 1072 - 5
Sorbera LA.Martin L.Castañer J.Castañer RM. Drugs Future 2001, 26: 285 - 6
Chen YL.Wang TC.Tzeng CC.Chang NC. Helv. Chim. Acta 1999, 82: 191 - 7
Trivedi KN.Rao SSM.Mistry SV.Desai SM. J. Indian Chem. Soc. 2001, 78: 579 - Related papers are:
-
8a
Mason TJ.Lorimer JP.Paniwnyk L.Harris AR.Wright PW. Synth. Commun. 1990, 20: 3411 -
8b
Hui W.Hongzhen L.Jijun C.Yi P.Yaozeng S. Synth. Commun. 1999, 29: 129 -
9a
Appendino G.Cravotto G.Tagliapietra S.Nano GM.Palmisano G. Helv. Chim. Acta 1990, 73: 1865 -
9b
Appendino G.Cravotto G.Palmisano G.Annunziata G.Toma L. J. Org. Chem. 1994, 59: 5556 -
9c
Appendino G.Cravotto G.Minassi A.Palmisano G. Eur. J. Org. Chem. 2001, 3711 -
10a
Appendino G.Cravotto G.Palmisano G.Annunziata R. Synth. Commun. 1996, 26: 3359 -
10b
Appendino G.Cravotto G.Palmisano G.Annunziata R. Tetrahedron 1998, 54: 10819 - 11
Cravotto G.Nano GM.Tagliapietra S. Synthesis 2001, 49 - 12
Cenini S.Cravotto G.Giovenzana GB.Palmisano G.Tollari S. Tetrahedron 1999, 55: 6577 -
13a
Appendino G.Cravotto G.Nano GM.Palmisano G. Synth. Commun. 1992, 22: 2205 -
13b
Cravotto, G.; Tagliapietra, S.; Nano, G. M.; Palmisano, G. Heterocycles in press.
-
14a
Breslow R.Rideout D. J. Am. Chem. Soc. 1980, 102: 7816 -
14b
Breslow R. Acc. Chem. Res. 1991, 24: 159 -
15a
Brennen CE. Cavitation and Bubble Dynamics Oxford University Press; Oxford: 1995. -
15b
Luche JL. Synthetic Organic Sonochemistry Plenum Press; New York: 1998. -
16a
Cintas P.Luche J.-L. Green Chem. 1999, 1: 115 -
16b
Low CMR. Ultrasonics Sonochem. 1995, 2: 153 -
16c
Luche J.-L. Ultrasonics Sonochem. 1997, 4: 211 - 17
Lindley J. Ultrasonics 1992, 30: 163 -
18a
Broeckaert L.Caulier T.Fabre O.Maerschalk C.Reisse J.Vandercammen J.Yang DH.Lepoint T.Mullie F. Current Trends in SonochemistryPrice GJ. The Royal Society of Chemistry; London UK: 1992. -
18b
Lindley J.Mason TJ. Chem. Soc. Rev. 1987, 16: 275 -
19a For
the use of water as solvent in aldehydes condensation reactions:
Bigi F.Carloni S.Ferrari L.Maggi R.Mazzacani A.Sartori G. Tetrahedron Lett. 2001, 42: 5203 -
19b
Brufola G.Fringuelli F.Piermatti O.Pizzo F. Heterocycles 1996, 43: 1257 -
20a
Appendino G.Cravotto G.Tagliapietra S.Nano GM.Palmisano G.Ferraro S. Helv. Chim. Acta 1991, 74: 1451 -
20b
Appendino G.Cravotto G.Nano GM.Palmisano G.Annunziata R. Helv. Chim. Acta 1993, 76: 1194 -
21a
Gonzalez AG.Diaz CE.Jorge D.Lopez D.Rodriguez L. An Quim. Ser. C 1981, 77: 63 -
21b
Majumdar KC.Khan AT. Indian J. Chem., Sect. B 1990, 29: 483 -
22a
Ashby EC.Sun X.Duff JL. J. Org. Chem. 1994, 59: 1270 -
22b
Bordwell FG.Harrelson JA. J. Org. Chem. 1989, 54: 4893 -
22c
Kegelaers Y.Delplancke J.-L.Reisse J. Chimia 2000, 54: 48 - 23
Mason TJ.Lorimer JP.Mistry BP. Tetrahedron 1985, 41: 5201 -
24a
Murray RDH. In: Progress in the Chemistry of Organic Natural Products: Herz W., Kirby G.W., Moore G. W., Steglich R. E., Tamm W. Springer; Wien: 1991. Vol. 58. p.83-283 -
24b
Murray RDH. In: Progress in the Chemistry of Organic Natural Products: Herz W., Kirby G.W., Moore G. W., Steglich R. E., Tamm W. Vol. 72: Springer; Wien: 1997. p.1-119 -
24c
Estevez-Brown A.Gonzales AG. Nat. Prod. Rep. 1997, 14: 465 - 25
Suzuki E.Katsuragawa B.Inoue S. J. Chem. Research, Synop. 1979, 110 - 26
Hihn J.-Y.Bereziat D.Doche M.-L.Chaillet P.Lorimer JP.Mason TJ.Pollet B. Ultrasonics Sonochem. 2002, 9: 113