Abstract
Bi(NO3)3.5H2O, Bi(TFA)3 and Bi(OTf)3 were found to be highly powerful and practical catalysts for the synthesis of azalactones under solvent free conditions with excellent yields. In addition, high chemoselectivity for this synthesis has been achieved. Selective condensation of aryl aldehydes in the presence of aliphatic aldehydes, is another advantage of this procedure.
References
1.
(a)
Konkel J.T.
,
Fan J.
,
Jayachandran B.
, and
Kirk K. L.
, J. Fluorine Chem. , 2002 , 115 , 27 .
2.
Gootwald K.
, and
Seebach D.
, Tetrahedron , 1999 , 55 , 723 .
3.
Meiwes J.
,
Schudock M.
, and
Kretzschmar G.
, Tetrahedron Asymmetry , 1997 , 8 , 527 .
4.
Seebach D.
,
Jaeschke G.
,
Gottwald K.
,
Matsuda K.
,
Breuning M.
, and
Bringmann G.
, Tetrahedron , 1997 , 22 , 7359 .
5.
Cativela C.
,
Diaz-de-Villegas M. D.
,
Garcia J. I.
,
Jimenez A. I.
, Tetrahedron , 1997 , 53 , 4479 .
6.
Bautista F.M.
,
Campelo J. M.
,
Garcia D. L.
, and
Marinas J. M.
, Amino Acids , 1992 , 2 , 87 .
7.
(a)
Mitra S.N.
,
Dey S.
,
Karthikeyan S.
, and
Singh T. P.
, Biopolymers , 1997 , 41 , 1997 .
8.
Cavalier F.
, and
Verducci J.
, Tetrahedron Lett. , 1995 , 36 , 4425 .
9.
(a)
Avenoza A.
,
Busto J. H.
,
Cativiela C.
, and
Peregrina J. M.
, Tetrahedron Lett. , 2002 , 43 , 4167 .
10.
Cannella R.
,
Clerici F.
,
Gelmi M. L.
,
Penso M.
, and
Pocar D.
, J. Org. Chem. , 1996 , 61 , 1854 .
11.
Croce P.D.
,
Ferraccioli R.
, and
La-Rosa C.
, J. Chem. Soc. Perkin Trans. 1 , 1994 , 2499 .
12.
Bossio R.
,
Marcaccini S.
,
Pepino R.
, and
Paoli P.
, J. Heterocycl. Chem. , 1994 , 31 , 729 .
13.
(a)
Chikere A.C.
,
Galunsky B.
,
Schünemann V.
, and
Kasche V.
, Enzyme. Microb. Technol. , 2001 , 28 , 168 .
14.
Penalba J.
,
Puchades R.
,
Maquieira A.
,
Gee S.
, and
Hammock B. D.
, Biosens. Bioelectron. , 2000 , 15 , 99 .
15.
Gonzalez-Martinez M.A.
,
Puchades R.
,
Maquieira A.
,
Ferrer I.
,
Marco M. P.
, and
Barceló D.
, Anal. Chim. Acta. , 1999 , 386 , 201 .
16.
Kojima S.
,
Ohkawa H.
,
Hirano T.
,
Maki S.
,
Niwa H.
,
Ohashi M.
,
Inouye S.
, and
Tsuji F. I.
, Tetrahedron Lett. , 1998 , 39 , 5242 .
17.
(a)
Gelmi M.L.
,
Clerici F.
,
Melis A.
, Tetrahedron , 1997 , 53 , 1843 .
18.
Abd-el-Rahm A.H.
,
Kandeel E. M.
,
Abdel-Razik E. A.
,
El-Ghamry I. A.
, An. Quim. , 1993 , 89 , 237 .
19.
(a)
Kitazawa M.
,
Higuchi R.
,
Takahashi M.
,
Wada T.
, and
Sasabe H.
, J. Phys. Chem. , 1995 , 99 , 14784 .
20.
Icli S.
,
Icil H.
,
Alp S.
,
Koc H.
,
McKillop A.
, Spectrosc. Lett. , 1994 , 27 , 1115 .
21.
Patra A.
,
Ghosh G.
,
Mukhopadhyay P. K.
, J. Ind. Chem. Soc. , 1987 , 64 , 414 .
22.
Dhoubhadel S.P.
, J. Ind. Chem. Soc. , 1986 , 63 , 757 .
23.
Filler R.
, Advances in Heterocyclic Chemistry , Academic Press , New York , 1954 , 75 .
24.
(a)
Cativiela C.
,
Diaz-de-villegas M. D.
, and
Galvez J. A.
, Tetrahedron Lett. , 1999 , 40 , 1027 .
25.
Cativiela C.
, and
Melendez E.
, Synthesis. 1978 , 832 .
26.
Baltazzi E.
, and
Davis E. A.
, Chemy Ind. (Lond.) 1962 , 929 .
27.
Rao Y.S.
, J. Org. Chem. , 1976 , 41 , 722 .
28.
(a)
Kashyap J.
,
Chetry A. B.
,
Das P. J.
, Synth. Commun. , 1998 , 28 , 4187 .
29.
Ringold H.J.
,
Loeken B.
,
Rosenkranz G.
, and
Sondheimer F.
, J. Am. Chem. Soc. , 1956 , 78 , 816 .
30.
Bautista F.M.
,
Campelo J. M.
,
Garcia A.
,
Luna D.
,
Marinas J. M.
, and
Romero A. A.
, J Chem. Soc. Perkin Trans. 2 , 2002 , 227 .
31.
Monk K.A.
,
Sarapa D.
, and
Mohan R. S.
, Synth. Commun. , 2000 , 30 , 3167 .
32.
Rao P.S.
, and
Venkatratnam R. V.
, Ind. J. Chem. , 1994 , 33B , 984 .
33.
Kidwai M.
,
Kumar R.
, and
Kumar P.
, Ind. J. Chem. , 1996 , 35B , 1004 .
34.
(a)
Cunha S.
,
Lima B. R.
, and
Souza A. R.
, Tetrahedron Lett. , 2002 , 43 , 49 .
35.
Keramane E.M.
,
Boyer B.
, and
Roque J. P.
, Tetrahedron , 2001 , 57 , 1909 .
36.
Keramane E.M.
,
Boyer B.
, and
Roque J. P.
, Tetrahedron Lett. , 2001 , 42 , 855 .
37.
Laurent-Robert H.
, and
Dubac J.
, Synlett , 1998 , 1138 .
38.
(a)
Suzuki H.
, and
Matano Y.
, Organobismuth Chemistry , Elsevier , Amsterdam , 2001 .
39.
Reglinski J.
, In Chemistry of Arsenic Antimony and Bismuth , Blacki Academic and Professional , New York , 1998 .
40.
Suzuki H.
,
Ikagami T.
,
Matano Y.
, Synthesis , 1997 , 249 .
41.
Marshall J.A.
, Chemtracts. , 1997 , 1064 .
42.
(a)
Mohammadpoor-Baltork I.
, and
Khosropour A. R.
, Monatshefte für Chemie , 2002 , 133 , 189 .
43.
Mohammadpoor-Baltork I.
,
Khodaei M. M.
, and
Nikoofar K.
, Tetrahedron Lett. , 2002 , 44 , 591 .
44.
Mohammadpoor-Baltork I.
,
Aliyan H.
, and
Khosropour A. R.
, Tetrahedron , 2001 , 57 , 5851 .
45.
Mohammadpoor-Baltork I.
, and
Khosropour A. R.
, Molecules , 2001 , 6 , 996 .
46.
Mohammadpoor-Baltork I.
,
Khosropour A. R.
, and
Aliyan H.
, J. Chem. Res.(S) , 2001 , 7 , 780 .
47.
Mohammadpoor-Baltork I.
,
Khosropour A. R.
, and
Aliyan H.
, Synth. Commun. , 2001 , 22 , 3411 .
48.
(a)
Répichet S.
,
Zwick A.
,
Vendier L.
,
Le Roux C.
, and
Dubac J.
, Tetrahedron Lett. , 2002 , 43 , 993 .
49.
Garner C.D.
, and
Hughes B.
, Advances in Inorganic Chemistry and Radiochemistry , Vol 17 . Academic Press , New York , 1975 .
50.
Singh S.
, and
Verma A. R. D.
, Indian J. Chem. , 1983 , 22A , 814 .
51.
(a)
Dakin H.D.
, J. Biol. Chem. , 1911 , 9 , 151 .
52.
Dakin H.D.
, J. Biol. Chem. , 1911 , 9 , 11 .
53.
Pschorr V. R.
Justus Liebig's Annalen der Chimie , 1912 , 391 , 40 .
54.
Douglas R.L.
, and
Gulland J. M.
, J. Chem. Soc. , 1931 , 2893 .
55.
Crawford M.
, and
Little W. T.
, J. Chem. Soc. , 1959 , 729 .
56.
Shueler F.W.
, and
Wang S. C.
, J. Am. Chem. Soc. , 1950 , 72 , 2220 .
57.for entry 4 : IR (KBr) 3026, 1776, 1744 cm−1, 1H NMR (200 MHz, CDCl3) δ 7.37 (1H, s); 7.4-7.78 (10H, m); 8.24 (2H, d, J =10.5 Hz); 8.31(2H, d, J = 9.5 Hz), 13C NMR (CDCl3) δ 125.3(C), 126(CH); 126.8(C); 127.5(CH); 127.7(CH); 127.9(CH); 128.2(CH); 128.5(CH); 128.8(CH); 128.2(CH); 129.4(CH); 130.2(C); 131,7(CH); 132.9(C); 133.4(CH); 133.6(CH); 133.7(CH); 140.5(CH); 144.2(C); 163.9(CH); 168.1(C); 169.2(C); MS (EI): 325 (M+). Anal. Calcd for C22H15NO2: C, 81.23%; H, 4.61%; N, 4.31%. found: C, 81.47%; H, 4.83%; N, 4.71%.
58.
This product was prepared by established method using Erlenmeyer procedure in the presence of Ac2O and NaOAc and melting point of the product compared with that obtained by this new method.