Abstract
The classical Biginelli reaction has been extended by the use of N-substituted ureas and thioureas. A set of N 1-alkyl-, N 1-aryl-, and N 1,N 3-dialkyl-3,4-dihydropyrimidin-2(1H )-(thi)ones was readily prepared in excellent yield when chlorotrimethylsilane in N ,N -dimethylformamide was used as promoter and water scavenger.
Key words
Biginelli reaction - heterocycles - Lewis acid - multicomponent reaction - parallel synthesis
References
1 Kappe CO.
Eur. J. Med. Chem.
2000,
35:
1043
2 Biginelli P.
Gazz. Chim. Ital.
1893,
23:
360
3a Kappe CO.
Tetrahedron
1993,
49:
6937
3b Kappe CO.
Acc. Chem. Res.
2000,
33:
879
4a Hu EH.
Sidler DR.
Dolling U.-H.
J. Org. Chem.
1998,
63:
3454
4b Lu J.
Bai Y.
Wang Z.
Yang B.
Ma H.
Tetrahedron Lett.
2000,
41:
9075
4c Ma Y.
Qian C.
Wang L.
Yang M.
J. Org. Chem.
2000,
65:
3864
4d Ranu BC.
Hajra A.
Jana U.
J. Org. Chem.
2000,
65:
6270
4e Fu NY.
Yuan YF.
Cao Z.
Wang SW.
Wang JT.
Peppe C.
Tetrahedron
2002,
58:
4801
4f Reddy CV.
Mahesh M.
Raju PVK.
Babu TR.
Reddy VVN.
Tetrahedron Lett.
2002,
43:
2657
4g Ramalinga K.
Vijayalakshmi P.
Kaimal TNB.
Synlett
2001,
863
4h Varala R.
Alam MM.
Adapa SR.
Synlett
2003,
67
4i Gourhari M.
Pradip K.
Chandrani G.
Tetrahedron Lett.
2003,
44:
2757
4j Yadav JS.
Reddy BVS.
Srinivas R.
Venugopal C.
Ramalingam T.
Synthesis
2001,
1341
4k Kumar KA.
Kasthuraiah M.
Reddy CS.
Reddy CD.
Tetrahedron Lett.
2001,
42:
7873
4l Yadav JS.
Reddy BVS.
Reddy KB.
Raj KS.
Prasad AR.
J. Chem. Soc., Perkin Trans. 1
2001,
1939
4m Jun L.
Yinjuan B.
Synthesis
2002,
466
4n Salehi P.
Dabiri M.
Zolfigol MA.
Fard MAB.
Tetrahedron Lett.
2003,
44:
2889
4o Sabitha G.
Reddy GSKK.
Reddy KB.
Yadav JS.
Tetrahedron Lett.
2003,
44:
6497
4p De S K.
Gibbs RA.
Synthesis
2005,
1748
4q Han X.
Xu F.
Luo Y.
Shen Q.
Eur. J. Org. Chem.
2005,
1500
5a Stadler A.
Kappe CO.
J. Chem. Soc., Perkin Trans. 1
2000,
1363
5b Stefani HA.
Gatti PM.
Synth. Commun.
2000,
30:
2165
5c Kappe CO.
Kumar D.
Varma RS.
Synthesis
1999,
1799
6a Lewandowski K.
Murer P.
Svec F.
Frechet JMJ.
Chem. Commun.
1998,
2237
6b Lewandowski K.
Murer P.
Svec F.
Frechet JMJ.
J. Comb. Chem.
1999,
1:
105
6c Wipf P.
Cunningham AA.
Tetrahedron Lett.
1995,
36:
7819
6d Kappe CO.
Bioorg. Med. Chem. Lett.
2000,
10:
49
6e Studer A.
Jeger P.
Wipf P.
Curran DP.
J. Org. Chem.
1997,
62:
2917
7a Shaabani A.
Bazgir A.
Teimouri F.
Tetrahedron Lett.
2003,
44:
857
7b Shaabani A.
Bazgir A.
Tetrahedron Lett.
2004,
45:
2575
7c Byk G.
Gottlieb H.
Herscovici J.
Mirkin F.
J. Comb. Chem.
2000,
2:
732
7d Abelman M.
Smith S.
James D.
Tetrahedron Lett.
2003,
44:
4559
7e Gong D.
Zhang L.
Yuan C.
Heteroat. Chem.
2003,
1:
13
7f Chiba T.
Sato H.
Kato T.
Heterocycles
1984,
22:
493
7g Sadanandam YS.
Shetty MM.
Diwan PV.
Eur. J. Med. Chem.
1992,
27:
87
8 Namazi H.
Mirzaei YR.
Azamat H.
J. Heterocycl. Chem.
2001,
38:
1051
9a Khanina EL.
Mutsenietse DK.
Kadysh VP.
Dubur GY.
Chem. Heterocycl. Compd.
1986,
22:
990
9b Kastron VV.
Vitolin’ RO.
Khanina EL.
Dubur GY.
Kimenis AA.
Pharm. Chem. J.
1987,
21:
571
10 Dallinger D.
Kappe CO.
Synlett
2002,
1901 ; and references cited therein
11 N ,N ′-dimethylurea in the Biginelli reaction, see: Jenner G.
Tetrahedron Lett.
2004,
45:
6195
12 Schnell B.
Krenn W.
Faber K.
Kappe CO.
J. Chem. Soc., Perkin Trans. 1
2000,
4382
13 Wannberg J.
Dallinger D.
Kappe CO.
Larhed M.
J. Comb. Chem.
2005,
7:
574
14a Vovk MV.
Sukach VA.
Russ. J. Org. Chem.
2005,
41:
1240
14b Sukach VA.
Bol’but AV.
Sinitsa AD.
Vovk MV.
Synlett
2006,
375
15a Ryabukhin SV.
Plaskon AS.
Tverdokhlebov AV.
Tolmachev AA.
Synth. Commun.
2004,
34:
1483
15b Ryabukhin SV.
Plaskon AS.
Volochnyuk DM.
Tolmachev AA.
Synlett
2004,
2287
15c Terechenko AD.
Sysoev DA.
Tverdokhlebov AV.
Tolmachev AA.
Synthesis
2006,
349
15d Ryabukhin SV.
Plaskon AS.
Volochnyuk DM.
Tolmachev AA.
Synthesis
2006,
3715
16a Zhu Y.-L.
Huang S.-L.
Pan Y.-J.
Eur. J. Org. Chem.
2005,
2354
16b Zhu Y.-L.
Pan Y.-J.
Huang S.-L.
Synth. Commun.
2004,
34:
3167
16c Zhu Y.-L.
Pan Y.-J.
Huang S.-L.
Heterocycles
2005,
65:
113
16d Zavyalov SI.
Kulikova LB.
Khim. Farm. Zh.
1992,
26:
116
16e Sabitha G.
Reddy GSKK.
Reddy CS.
Yadav JS.
Synlett
2003,
858
16f Bose DS.
Kumar RK.
Fatima L.
Synlett
2004,
279
17 Ryabukhin, S. V.; Mironets, R. V.; Plaskon, A. S.; Tolmachev, A. A. 10th Blue Danube Symposium on Heterocyclic Chemistry, Vienna, Austria, September 3-6 2003; PO-156.
18a Ciszewski L.
Xu D.
Li T.
Repic O.
Blacklock TJ.
Tetrahedron Lett.
1998,
39:
1107
18b Xu D.
Ciszewski L.
Li T.
Repic O.
Blacklock TJ.
Tetrahedron Lett.
2004,
45:
8091
19a Jahn U.
Schroth W.
Tetrahedron Lett.
1993,
34:
5863
19b Schroth W.
Jahn U.
Stroehl D.
Chem. Ber.
1994,
127:
2013
20 Huang S.
Pan Y.
Zhu Y.
Wu A.
Org. Lett.
2005,
7:
3797
