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Synthesis 2001(9): 1341-1345
DOI: 10.1055/s-2001-15229
DOI: 10.1055/s-2001-15229
PAPER
© Georg Thieme Verlag Stuttgart · New York
LiClO4-Catalyzed One-Pot Synthesis of Dihydropyrimidinones: An Improved Protocol for Biginelli Reaction [1]
Weitere Informationen
Received
4 January 2001
Publikationsdatum:
29. September 2004 (online)
Publikationsverlauf
Publikationsdatum:
29. September 2004 (online)
Abstract
Lithium perchlorate efficiently catalyzes the three-component condensation reaction of aldehyde, β-keto ester and urea in refluxing acetonitrile to afford the corresponding dihydropyrimidinones in high yields under neutral conditions. LiOTf is also found to be an efficient catalyst for the synthesis of dihydropyrimidinones from aldehyde, β-keto ester and urea.
Keywords
Biginelli reaction - lithium perchlorate - lithium triflate - dihydropyrimidinones
IICT Communication No. 4724.
- 2
Kappe CO. Tetrahedron 1993, 49: 6937 - 3
Kappe CO.Kumar D.Varma RS. Synthesis 1999, 1799 ; and references cited therein -
4a
Atwal KS.Rovnyak GC.O’Reilly BC.Schwartz J. J. Org. Chem. 1989, 54: 5898 -
4b
Atwal KS.Swanson BN.Unger SE.Floyd DM.Moreland S.Hedberg A.O’Reilly BC. J. Med. Chem. 1991, 34: 806 -
4c
Rovnyak GC.Atwal KS.Hedberg A.Kimball SD.Moreland S.Gougoutas JZ.O’Reilly BC.Schwartz J.Malley MF. J. Med. Chem. 1992, 35: 3254 -
4d
Kappe CO.Fabian WMF. Tetrahedron 1997, 53: 2803 -
5a
Patil AD.Kumar NV.Kokke WC.Bean MF.Freyer AJ.DeBrosse C.Mai S.Truneh A.Faulkner DJ. J. Org. Chem. 1995, 60: 1182 -
5b
Snider BB.Chen J.Patil AD.Freyer A. Tetrahedron Lett. 1996, 37: 6977 -
5c
Rama Rao RV.Gurjar MK.Vasudevan J. J. Chem. Soc., Chem. Commun. 1995, 1369 - 6
Biginelli P. Gazz. Chim. Ital. 1893, 23: 360 -
7a
Folkers K.Harwood HJ.Johnson TB. J. Am. Chem. Soc. 1932, 54: 3751 -
7b
Wipf P.Cunningham A. Tetrahedron Lett. 1995, 36: 7819 -
7c
Folkers K.Johnson TB. J. Am. Chem. Soc. 1934, 1180 -
8a
O’Reilly BC.Atwal KS. Heterocycles 1987, 26: 1185 -
8b
Atwal KS.O’Reilley BC.Gougoutas JZ.Malley MF. Heterocycles 1987, 26: 1189 -
8c
Shutalev AD.Kuksa VA. Khim. Geterotsikl. Soedin 1997, 105 -
8e
Shutalev AD.Kishko EA.Sivova N.Kuznetsov AY. Molecules 1998, 3: 100 -
9a
Hu EH.Sidler DR.Dolling U.-H. J. Org. Chem. 1998, 63: 3454 -
9b
Kappe CO.Falsone SF. Synlett 1998, 718 -
9c
Bigi F.Carloni S.Frullanti B.Maggi R.Sartori G. Tetrahedron Lett. 1999, 40: 3465 -
9d
Ranu BC.Hajra A.Jana U. J. Org. Chem. 2000, 65: 6270 -
9e
Lu J.Ma H. Synlett 2000, 63 -
9f
Ma Y.Qian C.Wang L.Yang M. J. Org. Chem. 2000, 65: 3864 -
10a
Yadav JS.Subba Reddy RV.Jagan Reddy E.Ramalingam T. J. Chem. Res., Synop. 2000, 354 -
10b
Gupta R.Gupta AK.Paul S.Kachroo PL. Indian J. Chem. 1995, 34B: 151 -
11a
Grieco PA. Aldrichimica Acta 1991, 24: 59 -
11b
Balasubramanian KK. Acros Org. Acta 1999, 6: 12
References
IICT Communication No. 4724.