Abstract
Sodium selenite in dimethylsulfoxide is a highly efficient reagent for dehydrogenation reactions and can be used under both thermal as well as microwave irradiation conditions. Using this reagent benzoins have been dehydrogenated to benzils, flavanones to flavones and 2′-hydroxy chalcones have been converted into flavones by cyclodehydrogenation.
References
1.
Doyle M.P.
,
Zuidema L.J.
, and
Bade T.R.
, J. Org. Chem. , 1975 , 40 , 1454 .
2.
Chakarvathi D.
, and
Dutta J.
, J. Indian Chem. Soc. , 1939 , 16 , 639 .
3.
Shirude S.T.
,
Patel P.
,
Giridhar R.
, and
Yadav M.R.
, Indian J. Chem. , 2006 , 45B , 1080 .
4.
Schoenberg G.
, and
Schuetz G.
, Chem. Ber. , 1960 , 93 , 1466 .
5.
Shanker G.
, and
Mallaiah B.V.
, Synthesis , 1984 , 310 .
6.
Bose P.K.
,
Chakrabarti P.
, and
Sanyal A.K.
, J. Indian Chem. Soc. , 1971 , 48 , 1163 .
7.
Bruke S.D.
, and
Danheiser R.L.
, Handbook of reagents for organic synthesis: oxidising and reducing agents , John Wiley & Sons : New York , 1999 , p. 90 .
8.
Gobbi S.
,
Rampa A.
,
Bisi A.
,
Belluti F.
,
Piazzi L.
,
Valent P.
,
Caputo A.
,
Zampiron A.
, and
Carrara M.
, J. Med. Chem. , 2003 , 46 , 3662 .
9.
Ahmed N.
,
Ali H.
, and
Van Lier J.E.
Tetrahedron Lett. , 2005 , 46 , 253 .
10.
Bruke S.D.
, and
Danheiser R.L.
, Handbook of reagents for organic synthesis: oxidising and reducing agents , John Wiley & Sons : New York , 1999 p. 358 .
11.
Material Safety Data Sheet available at http://ptcl.chem.ox.ac.uk/
12.
Ambramovich R.A.
, Org. Prep. Proced. Int. , 1991 , 23 .
13.
Caddick S.
, Tetrahedron , 1995 , 51 , 10403 .
14.
Rao K.V.
,
Chattopadhyay S.K.
, and
Reddy G.C.
, J. Agric. Food Chem. , 1990 , 38 , 1427 .
15.
Gee J.M.
, and
Johnson I.T.
, Curr, Med. Chem. , 2001 , 8 , 1245 .
16.
Pieta P.G.
, J. Nat. Prod , 2000 , 63 , 1035 .
17.
Zonali P.
,
Aallone R.
, and
Baraildi M.
, Filtoterapia , 2000 , 714 , 117 .
18.
Leu Y.I.
,
Cassady J.M.
, and
Cook V.M.
, J. Nat. Prod , 1992 , 55 , 357 .
19.
Fishkin R.J.
, and
Winslow J.T.
, Psychopharmacology (Berl.) , 1997 , 132 , 335 .
20.
Bannerjee N.R.
, and
Seshadri T.R.
, Current Sci. , 1956 , 25 , 143 .
21.
Hans N.
, and
Grover S.K.
, Synth. Commun. , 1993 , 102 .
22.
Doshi A.G.
,
Soni P.A.
, and
Ghiya B.G.
, Indian J. Chem. , 1986 , 25B , 759 .
23.
Mostahar S.
,
Alam S.
, and
Islam A.
, Indian J. Chem. , 2006 , 45B , 1478 .
24.
Massicot J.
, Compt. Rend. , 1955 , 240 , 94 .
25.
Kasahara A.
,
Izumi T.
, and
Ooshima M.
, Bull. Chem. Soc. Jpn. , 1974 , 47 , 2526 .
26.
Imafuku K.
, and
Honda K.
, Synthesis , 1987 , 199 .
27.
Hoshino Y.
,
Oohinata T.
, and
Takeno N.
, Bull. Chem. Soc. Jpn. , 1986 , 59 , 2351 .
28.
Klein B.
, J. Am. Chem. Soc. , 1941 , 63 , 1474 .
29.
Dann O.
, and
Mulius G.
, Liebigs Ann. Chem. , 1954 , 587 , 1 .
30.
Baker W.
, and
Glocking F.
, J. Chem. Soc. , 1950 , 2759 .
31.
Fitzgerald D.M.
,
O'Sullivan J.F.
,
Philbin E.M.
, and
Wheeler T.S.
, J. Chem. Soc. , 1955 , 860 .
32.
Narasimhachari N.
, and
Seshadri T.R.
, Proc Indian Acad. Sci. , 1949 , 30A , 151 .
33.
Mallik U.K.
,
Mallik A.K.
, and
Saha M.M.
, Indian J. Chem. , 1989 , 28B , 970 .
34.
Simonisn H.
, and
Danischewski D.
, Ber. , 1926 , 59 , 2914 .
35.
Dune A.T.M.
,
Gowan J.E.
,
Rocke M.M.
, and
Wheeler T.S.
, J. Chem. Soc. , 1950 , 1252 .