Abstract
The published data on the Biginelli reaction are generalised and systematised. The major attention is focused on the publications of the last seven years. Possible reaction mechanisms and its application for the synthesis of 3,4-dihydropyrimidin-2(1H)-one derivatives are considered. Examples of rare versions of this reaction are given.
References
1.
Biginelli P.
Berichte der deutschen chemischen Gesellschaft ,
1891
2.
Rovnyak G.C., Kimball S.D., Beyer B., Cucinotta G., DiMarco J.D., Gougoutas J., Hedberg A., Malley M., McCarthy J.P.
Journal of Medicinal Chemistry ,
1995
3.
Brands M., Endermann R., Gahlmann R., Krüger J., Raddatz S.
Bioorganic and Medicinal Chemistry Letters ,
2003
4.
Snider B.B., Shi Z.
Journal of Organic Chemistry ,
1993
5.
Folkers K., Johnson T.B.
Journal of the American Chemical Society ,
1933
6.
Steele T.G., Coburn C.A., Patane M.A., Bock M.G.
Tetrahedron Letters ,
1998
7.
Kappe C.O., Falsone S.F.
Synlett ,
1998
8.
Jauk B., Belaj F., Kappe C.O.
Journal of the Chemical Society Perkin Transactions 1 ,
1999
9.
Mirzaei Y.R., Azamat H., Namazi H.
Journal of Heterocyclic Chemistry ,
2001
10.
Bose D.S., Fatima L., Mereyala H.B.
Journal of Organic Chemistry ,
2002
11.
12.
Kappe C.O., Shishkin O.V., Uray G., Verdino P.
Tetrahedron ,
2000
13.
Schnell B., Krenn W., Faber K., Kappe C.O.
Journal of the Chemical Society Perkin Transactions 1 ,
2000
14.
Bigi F., Carloni S., Frullanti B., Maggi R., Sartori G.
Tetrahedron Letters ,
1999
15.
Lin H., Ding J., Chen X., Zhang Z.
Molecules ,
2000
16.
17.
Bhosale R.S., Bhosale S.V., Bhosale S.V., Wang T., Zubaidha P.K.
Tetrahedron Letters ,
2004
18.
19.
Bose A.K., Manhas M.S., Pednekar S., Ganguly S.N., Dang H., He W., Mandadi A.
Tetrahedron Letters ,
2005
20.
Salehi P., Dabiri M., Zolfigol M.A., Bodaghi Fard M.A.
Tetrahedron Letters ,
2003
21.
Hu E.H., Sidler D.R., Dolling U.
Journal of Organic Chemistry ,
1998
22.
23.
24.
Zorkun İ.S., Saraç S., Çelebi S., Erol K.
Bioorganic and Medicinal Chemistry ,
2006
25.
Jenner G.
Tetrahedron Letters ,
2004
26.
Ranu B.C., Hajra A., Jana U.
Journal of Organic Chemistry ,
2000
27.
Stadler A., Kappe C.O.
Journal of Combinatorial Chemistry ,
2001
28.
Yadav J.S., Subba Reddy B.V., Srinivas R., Venugopal C., Ramalingam T.
Synthesis ,
2001
29.
Ananda Kumar K., Kasthuraiah M., Suresh Reddy C., Devendranath Reddy C.
Tetrahedron Letters ,
2001
30.
31.
31
A. A. Krasnovskii
Biokhimiya ,
1960
32.
33.
Putilova E.S., Troitskii N.A., Zlotin S.G., Khudina O.G., Burgart Y.V., Saloutin V.I., Chupakhin O.N.
Russian Journal of Organic Chemistry ,
2006
34.
Putilova E.S., Kryshtal’ G.V., Zhdankina G.M., Troitskii N.A., Zlotin S.G.
Russian Journal of Organic Chemistry ,
2005
35.
Yadav J.S., Reddy B.V., Bhaskar Reddy K., Sarita Raj K., Prasad A.R.
Journal of the Chemical Society Perkin Transactions 1 ,
2001
36.
Ranu B.C., Hajra A., Dey S.S.
Organic Process Research and Development ,
2002
37.
Stefani H.A., Oliveira C.B., Almeida R.B., Pereira C.M., Braga R.C., Cella R., Borges V.C., Savegnago L., Nogueira C.W.
European Journal of Medicinal Chemistry ,
2006
38.
Dandia A., Saha M., Taneja H.
Journal of Fluorine Chemistry ,
1998
39.
Wannberg J., Dallinger D., Kappe C.O., Larhed M.
Journal of Combinatorial Chemistry ,
2005
40.
Lengar A., Kappe C.O.
Organic Letters ,
2004
41.
Desai B., Dallinger D., Kappe C.O.
Tetrahedron ,
2006
42.
Kidwai M., Saxena S., Mohan R., Venkataramanan R.
Journal of the Chemical Society Perkin Transactions 1 ,
2002
43.
44.
44
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1953
45.
Osnaya R., Arroyo G.A., Parada L., Delgado F., Trujillo J., Salmón M., Miranda R.
Arkivoc ,
2003
46.
46
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1955
47.
Syamala M.
Organic Preparations and Procedures International ,
2005
48.
Oliver Kappe C.
Tetrahedron ,
1993
49.
Kappe C.O.
Accounts of Chemical Research ,
2000
50.
Sweet F., Fissekis J.D.
Journal of the American Chemical Society ,
1973
51.
Kappe C.O.
Journal of Organic Chemistry ,
1997
52.
Xia M., Wang Y.
Tetrahedron Letters ,
2002
53.
54.
Wipf P., Cunningham A.
Tetrahedron Letters ,
1995
55.
Lusch M.J., Tallarico J.A.
Organic Letters ,
2004
56.
Valverde M.G., Dallinger D., Kappe C.O.
Synlett ,
2001
57.
Zhang L., Rana T.M.
Journal of Combinatorial Chemistry ,
2004
58.
Gross G.A., Wurziger H., Schober A.
Journal of Combinatorial Chemistry ,
2005
59.
Pérez R., Beryozkina T., Zbruyev O.I., Haas W., Kappe C.O.
Journal of Combinatorial Chemistry ,
2002
60.
Legeay J., Vanden Eynde J.J., Bazureau J.P.
Tetrahedron ,
2005
61.
Atwal K.S., Rovnyak G.C., O'Reilly B.C., Schwartz J.
Journal of Organic Chemistry ,
1989
62.
Ma Y., Qian C., Wang L., Yang M.
Journal of Organic Chemistry ,
2000
63.
Lu J., Bai Y., Wang Z., Yang B., Ma H.
Tetrahedron Letters ,
2000
64.
64
Chem. Zentr. II ,
1931
65.
Martı́nez S., Meseguer M., Casas L., Rodrı́guez E., Molins E., Moreno-Mañas M., Roig A., Sebastián R.M., Vallribera A.
Tetrahedron ,
2003
66.
Fu N., Yuan Y., Cao Z., Wang S., Wang J., Peppe C.
Tetrahedron ,
2002
67.
Sabitha G., Kumar Reddy G.S., Reddy C.S., Yadav J.S.
Synlett ,
2003
68.
Maiti G., Kundu P., Guin C.
Tetrahedron Letters ,
2003
69.
Li J., Han J., Yang J., Li T.
Ultrasonics Sonochemistry ,
2003
70.
Paraskar A.S., Dewkar G.K., Sudalai A.
Tetrahedron Letters ,
2003
71.
Shaabani A., Bazgir A., Teimouri F.
Tetrahedron Letters ,
2003
72.
Manhas M.S., Ganguly S.N., Mukherjee S., Jain A.K., Bose A.K.
Tetrahedron Letters ,
2006
73.
73
T. Skwarski
Chem. Abs. ,
1957
74.
Tu S., Fang F., Miao C., Jiang H., Feng Y., Shi D., Wang X.
Tetrahedron Letters ,
2003
75.
75
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1950
76.
76
A. N. Terenin
"Fotokhimiya Krasitelei" (The Photochemistry of Dyes) ,
1947
77.
Nagaiah K., Narsaiah A.V., Basak A.K.
Synthesis ,
2004
78.
Suzuki I., Suzumura Y., Takeda K.
Tetrahedron Letters ,
2006
79.
Zheng L., Wang T., Wei Z., Xiang J., Bai X.
Tetrahedron Letters ,
2005
80.
Cepanec I., Litvić M., Bartolinčić A., Lovrić M.
Tetrahedron ,
2005
81.
De S.K., Gibbs R.A.
Synthesis ,
2005
82.
Yu Y., Liu D., Liu C., Luo G.
Bioorganic and Medicinal Chemistry Letters ,
2007
83.
Rafiee E., Jafari H.
Bioorganic and Medicinal Chemistry Letters ,
2006
84.
Singh K., Arora D., Singh S.
Tetrahedron Letters ,
2006
85.
Debache A., Boumoud B., Amimour M., Belfaitah A., Rhouati S., Carboni B.
Tetrahedron Letters ,
2006
86.
Sabitha G., Reddy G.S., Reddy K.B., Yadav J.S.
Tetrahedron Letters ,
2003
87.
Peng J., Deng Y.
Tetrahedron Letters ,
2001
88.
Sabitha G., Reddy K.B., Yadav J.S., Shailaja D., Sivudu K.S.
Tetrahedron Letters ,
2005
89.
Huang Y., Yang F., Zhu C.
Journal of the American Chemical Society ,
2005
90.
Rosi Reddy K., Venkateshwar Reddy C., Mahesh M., Raju P.V., Narayana Reddy V.V.
Tetrahedron Letters ,
2003
91.
Zumpe F.L., Flüß M., Schmitz K., Lender A.
Tetrahedron Letters ,
2007
92.
Tu S., Fang F., Zhu S., Li T., Zhang X., Zhuang Q.
Synlett ,
2004
93.
93
V. B. Evstigneev
Dokl. Akad. Nauk SSSR ,
1956
94.
Stadler A., Kappe C.O.
Journal of the Chemical Society Perkin Transactions 2 ,
2000
95.
Mabry J., Ganem B.
Tetrahedron Letters ,
2006
96.
Abdel-Fattah A.A.
Synthesis ,
2003
97.
Salehi P., Dabiri M., Ali Zolfigol M., Baghbanzadeh M.
Heterocycles ,
2005
98.
Reddy C.V., Mahesh M., Raju P.V., Babu T.R., Reddy V.V.
Tetrahedron Letters ,
2002
99.
Fu N., Yuan Y., Pang M., Wang J., Peppe C.
Journal of Organometallic Chemistry ,
2003
100.
Abelman M.M., Smith S.C., James D.R.
Tetrahedron Letters ,
2003
101.
102.
Hassani Z., Islami M.R., Kalantari M.
Bioorganic and Medicinal Chemistry Letters ,
2006
103.
Zhidovinova M.S., Fedorova O.V., Rusinov G.L., Ovchinnikova I.G.
Molecular Diversity ,
2000
104.
Vdovina S.V., Mustakimova L.V., Mamedov V.A.
Russian Journal of Organic Chemistry ,
2008
105.
105
F. F. Litvin
Dokl. Akad. Nauk SSSR ,
1958
106.
Guillon J., Grellier P., Labaied M., Sonnet P., Léger J., Déprez-Poulain R., Forfar-Bares I., Dallemagne P., Lemaître N., Péhourcq F., Rochette J., Sergheraert C., Jarry C.
Journal of Medicinal Chemistry ,
2004
107.
Raines S., Chai S.Y., Palopoli F.P.
Journal of Heterocyclic Chemistry ,
1976
108.
Saloutin V.I., Burgart Y.V., Kuzueva O.G., Kappe C.O., Chupakhin O.N.
Journal of Fluorine Chemistry ,
2000
109.
Martins M.A., Teixeira M.V., Cunico W., Scapin E., Mayer R., Pereira C.M., Zanatta N., Bonacorso H.G., Peppe C., Yuan Y.
Tetrahedron Letters ,
2004
110.
110
M. F. Shostakovskii
Dokl. Akad. Nauk SSSR ,
1960
111.
Byk G., Gottlieb H.E., Herscovici J., Mirkin F.
Journal of Combinatorial Chemistry ,
2000
112.
Shaabani A., Bazgir A., Bijanzadeh H.R.
Molecular Diversity ,
2004
113.
Wang Z., Xu L., Xia C., Wang H.
Tetrahedron Letters ,
2004
114.
Liang B., Wang X., Wang J., Du Z.
Tetrahedron ,
2007
115.
Singh K., Singh J., Deb P.K., Singh H.
Tetrahedron ,
1999