Abstract
A variety of semicarbazones are transformed to their carbonyl compounds with quinolinium fluorochromate (QFC) in high yields under mild and non-aqueous conditions. Selective deprotection of semicarbazones and oximes in the presence of p-nitrophenylhydrazones or 2,4-dinitrophenylhydrazones is noteworthy advantage of this reagent.
References
1.
(a)
Gillam A.E.
, and
West T. F.
, J. Chem. Soc. , 1945 , 95 .
2.
Hershberg E.B.
, J. Org. Chem. , 1948 , 542 .
3.
Eisenbraun E.J.
,
Wesley R. P.
,
Budhram R. S.
, and
Dewprasad B.
, Chem. Ind. (London) 1989 , 549 .
4.
Greene T.W.
, and
Wuts P. G. M.
, Protective Groups in Organic Synthesis , 2nd edn., John Willey , New York , 1991 , pp. 172 –223 .
5.
Kirk D.N.
, and
Slade C. J.
, Tetrahedron Lett. , 1980 , 21 , 651 .
6.
Mcguckin W.F.
, and
Kendall E. C.
, J. Am. Chem. Soc. , 1952 , 74 , 5811 .
7.
Butler R.N.
,
Morris G. J.
, and
O'Donohue A. M.
, J. Chem. Res. (S) , 1981 , 61 .
8.
Ram R.N.
, and
Varsha K.
, Tetrahedron Lett. , 1991 , 32 , 5829 .
9.
Ranu B.C.
, and
Sarkar D. C.
, J. Org. Chem. , 1988 , 53 , 878 .
10.
Laszlo P.
, and
Polla E.
, Synthesis , 1985 , 439 .
11.
Narayanan S.
, and
Srinivasan V. S.
, J. Chem. Soc. Perkin Trans. 2 , 1986 , 1557 .
12.
Curini M.
,
Rosati O.
,
Pisani E.
, and
Costantino U.
, Synlett. , 1996 , 333 .
13.
Firozabadi H.
,
Seddighi M.
,
Ahmadi Z. A.
, and
Sardarian A. R.
, Synth. Commun. , 1989 , 19 , 3358 .
14.
Salmon M.
,
Miranda R.
, and
Angeles E.
, Synth. Commun. , 1986 , 16 , 1 .
15.
Zhang G.S.
,
Yang D. H.
,
Chen M. F.
, and
Cai K.
, Synth. Commun. , 1998 , 28 , 607 .
16.
Varma R.S.
, and
Meshram H. M.
, Tetrahedron Lett. , 1997 , 38 , 7973 .
17.
Gong H.
, and
Zhang G. S.
, Synth. Commun. , 1999 , 29 , 2591 .
18.
Mohammadpoor-Baltork I.
, and
Pourranshirvani S.
, Synth. Commun. , 1996 , 26 , 1 .
19.
Mohammadpoor-Baltork I.
,
Hajipour A. R.
, and
Haddadi R.
, J. Chem. Res. (S) , 1999 , 102 .
20.
Hajipour A.R.
,
Mallakpour S. E.
,
Mohammadpoor-Baltork I.
, and
Khoee S.
, Synth. Commun. , 2001 , 31 , 1187 .
21.
Zhang G.S.
,
Gong H.
,
Yang D. H.
, and
Chen M. F.
, Synth. Commun. , 1999 , 29 , 1165 .
22.
Cava M.P.
,
Little R. L.
, and
Napier D. R.
, J. Am. Chem. Soc. , 1958 , 80 , 2257 .
23.
Herzog H.L.
,
Payne C. C.
,
Jevnik M. A.
,
Gould D.
,
Shapiro E. L.
,
Oliveto E. P.
, and
Hershberg E. B.
, J. Am. Chem. Soc. , 1955 , 77 , 4781 .
24.
Minghu W.
,
Guichun Y.
, and
Zuxing C.
, Synth. Commun. , 2000 , 30 , 3127 .
25.
Ranu B.C.
, and
Sarkar D. C.
, J. Org. Chem. , 1988 , 53 , 878 .
26.
Ballini R.
, and
Petrini M.
, J. Chem. Soc. Perkin. Trans. 1 , 1988 , 2563 .
27.
Pines S.H.
,
Chemerda J. M.
, and
Kolowski M. A.
, J. Org. Chem. , 1966 , 31 , 3446 .
28.
(a)
Tajbakhsh M.
,
Mohammadpoor-baltork I.
, and
Alimohammadi S. K.
, Ind. J. Chem. , 2003 , 2638 .
29.
Tajbakhsh M.
,
Mohammadpoor-baltork I.
, and
Alimohammadi K.
, Monatsh. Chem. , 2003 , 134 , 1571 .
30.
Tajbakhsh M.
,
Mohammadpoorbaltork I.
, and
Ramzanian-lehmali F.
, Phosphorus, Sulfur, and Silicon , 2003 , 178 , 2620 .
31.
Tajbakhsh M.
,
Mohammadpoorbaltork I.
, and
Ramzanian-lehmali F.
, J. Chem. Res. (S) , 2003 , 710 .
32.
Tajbakhsh M.
,
Ghaemi M.
,
Sarabi S.
,
Ghassemzadeh M.
, and
Heravi M. M.
, Monatsh. Chem. , 2000 , 131 , 1213 .
33.
Tajbakhsh M.
,
Heravi M. M.
,
Mohanazadeh F.
,
Sarabi S.
, and
Ghassemzadeh M.
, Monatsh. Chem. , 2001 , 132 , 1229 .
34.
Tajbakhsh M.
,
Hosseinzadeh R.
, and
Niaki M. Y.
, J. Chem. Res. (S) , 2002 , 508 .
35.
Hosseinzadeh R.
,
Tajbakhsh M.
, and
Niaki M. Y.
, Tetrahedron Lett. , 2002 , 43 , 9413 .
36.
Tajbakhsh M.
,
Hosseinzadeh R.
, and
Shakoori A.
, Tetrahedron Lett. , 2004 , 45 , 1889 .
37.
Hosseinzadeh R.
,
Tajbakhsh M.
,
Shakoori A.
, and
Niaki M. Y.
, Monatsh. Chem. , 2004 , published online June 30.
38.
Vogel A.I.
, A Text Book of Practical Organic Chemistry , 4th edn., Longman , London , 1980 , pp. 1112 .
39.
Murugesan V.
, and
Pandurrangan A.
, Ind. Jo. Chem. , 1992 , 31 , 377 .