Abstract
Sulphamic acid (H2 NSO3 H, SA) is used as an alternative to conventional acid catalysts in the Pechmann condensation of phenols with β-ketoester leading to the formation of substituted coumarin. The method is simple, cost-effective, solvent-free and gives good yields in a short reaction time.
Key words
sulphamic acid - Pechmann reaction - coumarins
References
1
Kennedy RO.
Thornes RD.
Coumarins: Biology, Applications and Mode of Action
Wiley and Sons;
Chichester:
1997.
2
Murray RDH.
Medez J.
Brown SA.
The Natural Coumarins: Occurrence, Chemistry, and Biochemistry
Wiley;
New York:
1982.
3
Maeda M.
Laser Dyes
Academic Press;
New York:
1984.
4
Peter H.
Dev. Oncol.
1984,
22:
259
5
Sethna SM.
Shah NM.
Chem. Rev.
1945,
36:
1
6
Sethna SM.
Phadke R.
Org. React.
1953,
7:
1
7a
Appel H.
J. Chem. Soc.
1935,
1031
7b
Woods LL.
Sapp J.
J. Org. Chem.
1962,
27:
3703
7c
Ahmad ZS.
Desai RD.
Proc. - Indian Acad. Sci., Chem. Sci.
1937,
5A:
277 ; Chem Abstr. 1937, 31 , 5785
7d
Robinson R.
Weygand F.
J. Chem. Soc.
1941,
386
7e
Nadkarni AJ.
Kudav NA.
Ind. J. Chem., Sect. B
1981,
20:
719
8
Russell A.
Frye JR.
Org. Synth.
1941,
21:
22
9
Woods LL.
Sapp JJ.
J. Org. Chem.
1962,
27:
3703
10a
Simmonis H.
Remmert P.
Chem. Ber.
1914,
47:
2229
10b
Robertson A.
Sandrock WF.
Henry CB.
J. Chem. Soc.
1931,
2426
11a
John EVO.
Israelstam SS.
J. Org. Chem.
1961,
26:
240
11b
Chaudhari DA.
Chem. Ind.
1983,
568
11c
Hoefnagel AJ.
Gunnewegh EA.
Downing RS.
van Bekkum H.
J. Chem. Soc., Chem. Commun.
1995,
225
12a
Singh V.
Singh J.
Kaur KP.
Kad GL.
J. Chem. Res., Synop.
1997,
58
12b
Singh J.
Kaur J.
Nayyar S.
Kad GL.
J. Chem. Res., Synop.
1998,
280
12c
de la Hoz A.
Moeno A.
Vazquez E.
Synlett
1999,
608
12d
Frere S.
Thiery V.
Besson T.
Tetrahedron Lett.
2001,
42:
2791
13a
Potdar MK.
Mohile SS.
Salunkhe MM.
Tetrahedron Lett.
2001,
42:
9285
13b
Khandekar AC.
Khadilkar BM.
Synlett
2002,
152
14a
Nonose N.
Kubota M.
J. Anal. Atom. Spectrom.
1998,
13:
151
14b
Kanda HA.
King AJ.
J. Am. Chem. Soc.
1951,
73:
2315
14c
Harbison GS.
Kye YS.
Penner GH.
Grandin M.
Monette M.
J. Phys. Chem. B
2002,
106:
10285
15a
Jin TS.
Sun G.
Li YW.
Li TS.
Green Chem.
2002,
4:
255
15b
Yiming L.
Meilian L.
Huaxue Shijie
1988,
39:
407
15c Fukunishi A, and Mori M. inventors; Japanese Patent
JP-06145102 [94145102].
15d
Yuqin W.
Jianguang X.
Huagong Shikan
1999,
13:
21
15e
Jin L.
Ru-Qi Z.
Hecheng Huaxue
2000,
8:
364
15f
Tong-shou J.
Synth. Commun.
1998,
28:
3173
15g
Daohua L.
Bi W.
Huaxue Shijie
2000,
41:
373
15h
Wang B.
Yang L.
Suo J.
Synth. Commun.
2003,
33:
3929
15i
Bo W.
Ming YL.
Shuan SJ.
Tetrahedron Lett.
2003,
44:
5037
15j
Wang B.
Yang L.
Yang T.
Yang L.
Suo J.
Tetrahedron Lett.
2004,
3369
16
Typical Experimental Procedure: To the weighed quantity of phenol (10 mmol), and β-keto ester (10 mmol), the sulphamic acid (5 mmol) was added and the reaction mixture was stirred at 130 °C in a pre-heated oil-bath. After completion of the reaction at the desired time as indicated in Table
[1 ]
, the reaction mixture was poured into water and the resultant product was filtered. The products were further purified by column chromatography. The compounds are well known and in agreement with spectral and physical data.