Abstract
A simple liquid phase synthetic method for the preparation of 4-methyl coumarin on modified poly(ethylene glycol)s by using the von Pechmann reaction is described.
Key words
von Pechmann condensation - multicomponent reaction - liquid phase synthesis - heterocycles - coumarins
References
1 Presented at the 5th Spanish Italian Symposium on Organic Chemistry, Santiago de Compostela, Spain, 10-13 September 2004.
2
Kurth MJ.
Sammelson RE.
Chem. Rev.
2001,
101:
137
3
Wentworth P.
Janda KD.
Chem. Commun.
1999,
1917
4
Früchtel JS.
Jung G.
Angew. Chem., Int. Ed. Engl.
1996,
35:
17
5
Thompson LA.
Ellman JA.
Chem. Rev.
1996,
96:
555
6a
Dickerson TJ.
Reed NN.
Janda KD.
Chem. Rev.
2002,
102:
3325
6b
Zhao X.
Metz WA.
Sieber F.
Janda KD.
Tetrahedron Lett.
1998,
39:
8433
6c
Gravert DJ.
Janda KD.
Curr. Opin. Chem. Biol.
1997,
1:
107
7a
Greenwald RB.
J. Controlled Release
2001,
74:
159
7b
Veronese F.
Morpurgo M.
Farmaco
1999,
54:
497
8a
Bonora GM.
Tocco G.
Caramella S.
Veronese FM.
Pliasunova O.
Pokorovsky A.
Ivanova E.
Zarytova V.
Farmaco
1998,
53:
634
8b
Annunziata R.
Benaglia M.
Cinquini M.
Cozzi F.
Tocco G.
Org. Lett.
2000,
2:
1737
8c
Benaglia M.
Cinquini M.
Cozzi F.
Tocco G.
Tetrahedron Lett.
2002,
43:
3391
8d
Danelli T.
Annunziata R.
Benaglia M.
Cinquini M.
Cozzi F.
Tocco G.
Tetraedron: Asymmetry
2003,
14:
461
9a
Begala M.
Delogu G.
Maccioni E.
Podda G.
Tocco G.
Quezada E.
Uriarte E.
Fedrigo MA.
Favretto D.
Traldi P.
Rapid Commun. Mass Spectrom.
2001,
15:
1000
9b
Begala M.
Gonzalez-Gomez JC.
Podda G.
Santana L.
Tocco G.
Uriarte E.
Rapid Commun. Mass Spectrom.
2004,
18:
564
10
Von Pechmann H.
Duisberg C.
Ber. Dtsch. Chem. Ges.
1884,
17:
929
11a
Ito C.
Itoigawa M.
Katsuno S.
Omura M.
Tokuda H.
Nishino H.
Furukawa H.
J. Nat. Prod.
2000,
639:
1218
11b
Tanaka T.
Kumamoto T.
Ishikawa T.
Tetrahedron Lett.
2000,
41:
10229
12
Erk C.
Gocmen A.
Bulut M.
Supramol. Chem.
2000,
11:
49
13
Trenor SR.
Shultz AR.
Love BJ.
Long TE.
Chem. Rev.
2004,
104:
3059
14
Trenor SR.
Love BJ.
Long TE.
Macromol. Chem. Phys.
2004,
205:
715
15
Jonson JR.
Org. React.
1942,
1:
210
16
Jones G.
Org. React.
1967,
15:
204
17
Brufola G.
Fringuelli F.
Piermatti O.
Pizzo F.
Heterocycles
1996,
43:
1257
18
Shriner RL.
Org. React.
1942,
1:
1
19
Narasimahan NS.
Mali RS.
Barve MV.
Synthesis
1979,
906
20
Yavari I.
Hekmat-Shoar R.
Zonouzi A.
Tetrahedron Lett.
1998,
39:
2391
21
Takeuchi Y.
Ueda N.
Uesugi K.
Abe H.
Nishioka H.
Harayama T.
Heterocycles
2003,
59:
217
22
Tu S.
Zhou J.-F.
Cai P.
Wang H.
Feng J.
Synth. Commun.
2001,
31:
3729
23
Bose DS.
Rudradas AP.
Hari Babu MH.
Tetrahedron Lett.
2002,
43:
9195
24
Bahekar SS.
Shinde DB.
Tetrahedron Lett.
2004,
45:
7999
25
Annunziata R.
Benaglia M.
Cinquini M.
Cozzi F.
Eur. J. Org. Chem.
2002,
1184
26
Sethna S.
Phadke R.
Org. React.
1960,
7:
2
27
Annunziata R.
Benaglia M.
Cinquini M.
Cozzi F.
Pitillo M.
J. Org. Chem.
2001,
66:
3160
28a
Pan PC.
Sun CM.
Tetrahedron Lett.
1998,
39:
9505
28b
Shey JY.
Sun CM.
Synlett
1998,
1423
28c
Shey JY.
Sun CM.
J. Comb. Chem.
1999,
1:
361
29a
Fishman A.
Farrah ME.
Zhong J.-H.
Paramanantham S.
Carrera C.
Lee-Ruff E.
J. Org. Chem.
2003,
68:
9843
29b
Vertes A.
Gijbels R.
Adams F.
Laser Ionization Mass Spectrometry
John Wiley;
New York:
1993.
30
von Pechmann H.
von Krafft E.
Ber. Dtsch. Chem. Ges.
1901,
34:
421
31a
Harris JM. In Poly(Ethylene Glycol) Chemistry: Biotechnical and Biomedical Applications
Harris JM.
Plenum Press;
New York:
1992.
p.2
31b
Zhao XY.
Metz WA.
Sieber F.
Janda KD.
Tetrahedron Lett.
1998,
39:
8433
32 Analytical details for compounds 9 and 15. 9. 1H NMR (300 MHz, CDCl3): δ = 2.40 (s, 3 H), 3.36 (s, 3 H), 6.20 (s, 1 H), 6.80 (s, 4
J = 2.43 Hz, 1 H), 6.90 (d, 3
J = 8.50 Hz, 4
J = 2.43 Hz, 1 H), 7.60 (s, 3
J = 8.50 Hz, 1 H). 15.
1H NMR (300 MHz, CDCl3): δ = 1.81 (m, 2 H), 2.40 (s, 3 H), 2.70 (t, 2 H), 3.36 (s, 3 H), 3.92 (t, 2 H), 6.18 (d, 3
J = 8.50 Hz, 2 H), 6.30 (s, 1 H), 6.81 (d, 3
J = 8.41, 1 H), 6.88 (s, 1 H), 6.98 (d, 3
J = 8.50, 2 H), 7.50 (d, 3
J = 8.41, 1 H).