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Synthesis 2005(8): 1301-1304
DOI: 10.1055/s-2005-861876
DOI: 10.1055/s-2005-861876
PAPER
© Georg Thieme Verlag Stuttgart · New York
Bi(NO3)3·5H2O-TBAF as an Efficient Reagent for in situ Oxidation: Dihydropyrimidinone Formation from Benzyl Halides
Further Information
Received
17 November 2004
Publication Date:
17 March 2005 (online)
Publication History
Publication Date:
17 March 2005 (online)
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Abstract
The oxidation of benzyl halides to aldehydes with bismuth nitrate pentahydrate in an ionic liquid was studied. Also, an efficient one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones from benzyl halides using bismuth nitrate pentahydrate in tetrabutylammonium fluoride (TBAF) as an in situ oxidant and catalyst is described.
Key words
dihydropyrimidinones - benzyl halides - oxidation-cyclocondensation - Bi(NO3)3·5H2O-TBAF - ionic liquid
-
1a
Studer A.Jeger P.Wipf P.Curran DP. J. Org. Chem. 1997, 62: 2917 -
1b
Kappe CO. Acc. Chem. Res. 2000, 33: 879 -
2a
Atwal KS.Swanson BN.Unger SE.Floyd DM.Moreland S.Hedberg A.O’Reilly BC. J. Med. Chem. 1991, 34: 806 -
2b
Rovnyak GC.Atwal KS.Hedberg A.Kimball SD.Moreland S.Gougoutas JZ.O’Reilly BC.Schwart J.Malley M. J. Med. Chem. 1992, 35: 3254 -
2c
Rovnyak GC.Kimball SD.Beyer B.Cucinotta G.DiMarco JD.Gougoutas JZ.Hedberg A.Malley M.McCathy JP.Zhang R.Moreland S. J. Med. Chem. 1995, 38: 119 -
2d
Kappe CO.Fabian WMF.Semones MA. Tetrahedron 1997, 53: 2803 -
3a
Snider B.Shi Z. J. Org. Chem. 1993, 58: 3828 -
3b
Overman LE.Rabinowitz MH.Renhowe PA. J. Am. Chem. Soc. 1995, 117: 2657 - 4
Biginelli P. Gazz. Chim. Ital. 1893, 23: 360 -
5a
Hu EH.Sidler DR.Dolling UH. J. Org. Chem. 1998, 63: 3454 -
5b
Kappe CO.Falsone SF. Synlett 1998, 718 -
5c
Singh K.Singh J.Deb PK.Singh H. Tetrahedron 1999, 55: 12873 -
5d
Yun M.Changtao Q.Limin W.Min Y. J. Org. Chem. 2000, 65: 3864 -
5e
Ranu BC.Hajra A.Jana U. J. Org. Chem. 2000, 65: 6270 -
5f
Kumar KA.Kasthuraiah M.Reddy CS.Reddy CD. Tetrahedron Lett. 2001, 42: 7873 -
5g
Ramalinga K.Vijayalakshmi P.Kaimal TNB. Synlett 2001, 863 -
5h
Dondoni A.Massi A. Tetrahedron Lett. 2001, 42: 7975 -
5i
Yadav JS.Subba Reddy BV.Srinivas R.Venugopal C.Ramalingam T. Synthesis 2001, 1341 -
5j
Fu N.Yuan Y.Cao Z.Wang S.Wang J.Peppe C. Tetrahedron 2002, 58: 4801 -
5k
Fan X.Zhang X.Zhang Y. J. Chem. Res., Synop. 2002, 436 -
5l
Jin T.Zhang S.Guo J.Li T. J. Chem. Res., Synop. 2002, 37 -
5m
Varala R.Alam MM.Adapa SR. Synlett 2003, 67 -
5n
Bose DS.Fatima L.Mereyala HB. J. Org. Chem. 2003, 68: 587 -
5o
Mukut G.Prajapati D.Sandhu JS. Synlett 2004, 235 -
6a
Bigi F.Carloni S.Frullanti B.Maggi R.Sartori G. Tetrahedron Lett. 1999, 40: 3465 -
6b
Kappe CO.Kumar D.Varma RS. Synthesis 1999, 1799 -
6c
Dondoni A.Massi A. Tetrahedron Lett. 2001, 42: 7975 -
7a
Kileny SN. In Comprehensive Organic SynthesisTrost BM.Ley SV. Pergamon Press; Oxford: 1991. Vol. 7. p.653 -
7b
Chandrasekhar S.Sridhar M. Tetrahedron Lett. 2000, 41: 5423 -
7c
Itoh A.Kodana T.Inagaki S.Masaki Y. Org. Lett. 2000, 2: 2455 - 8
Khodaei MM.Khosropour AR.Bigzadeh M. Synth. Commun. 2004, 34: 1551 - 9
Mohammadpoor-Baltork I.Khodaei MM.Nikoofar K. Tetrahedron Lett. 2003, 44: 591 - 10
Rappoport Z. Handbook of Tables for Organic Compound Identification CRC Press; Boca Raton: 1976. 3rd Ed.. -
11a
Lu J.Bai Y. Synthesis 2002, 467 -
11b
Rosi Reddy K.Venkateshwar Reddy C.Mahesh M.Raju PVK.Narayana Reddy VV. Tetrahedron Lett. 2003, 44, 8173 -
11c
Tu S.Fang F.Zhu S.Li T.Zhang S.Zhuang O. Synlett 2004, 537 -
11d
Fan X.Zhang X.Zhang Y. J. Chem. Res., Synop. 2002, 436 -
11e
Ma Y.Qian L.Wang L.Yang M. J. Org. Chem. 2000, 65: 3864 -
11f
Yadav JS.Subba Reddy BV.Jagan Reddy E.Ramalingam T. J. Chem. Res., Synop. 2000, 354