Abstract
A green and efficient synthesis of [1,3]oxazines has been achieved via a three-component, one-pot condensation of 4-hydroxycoumarin, potassium selenocyanate and acyl chlorides in the presence of N-methylimidazole under solvent-free conditions at ambient temperature.
Keywords
References
1.
Wirth T.
, Organoselenium chemistry: synthesis and reactions. Wiley-VCH , Weinheim , 2012 .
2.
Sydnes M.O.
, and
Isobe M.
, Monatsh. Chem. , 2015 , 146 , 351 .
3.
Razus A.C.
,
Birzan L.
,
Hanganu A.
,
Cristea M.
,
Ungureanu E.-M.
,
Soare M.-L.
, and
Buica G.-O.
, Monatsh. Chem. , 2014 , 145 , 1999 .
4.
Rvović M.D.
,
Divac V. M.
,
Janković N.Ž.
, and
Bugarčić Z. M.
, Monatsh. Chem. , 2013 , 144 , 1227 .
5.
Filipović N.
,
Polović N.
,
Rašković B.
,
Misirlić-Denćić S.
,
Dulović M.
,
Savić M.
,
Nikšić M.
,
Mitić D.
,
Andelković K.
, and
Todorović T.
, Monatsh. Chem. , 2014 , 145 , 1089 .
6.
Banert K.
, and
Toth C.
, Angew. Chem. Int. Ed. , 1995 , 34 , 1627 .
7.
Douglas I.B.
, J. Am. Chem. Soc. , 1937 , 59 , 740 .
8.
Krantz A.
,
Spencer W. R.
,
Tam F. T.
,
Liak J. T.
,
Copp J. L.
,
Thomas M. E.
, and
Rafferty P. S.
, J. Med. Chem. , 1990 , 33 , 464 .
9.
Gutschow M.
,
Kuerschner L.
,
Neumann U.
,
Pietsch M.
,
Loser R.
,
Koglin N.
, and
Eger K.
, J. Med. Chem. , 1999 , 42 , 5437 .
10.
Hsieh W.P.
,
Chang R. F.
,
Chang H. C.
,
Cheng W. P.
,
Chiang C. L.
,
Zeng L. F.
,
Lin K. H.
, and
Wu C. Y.
, Bioorg. Med. Chem. Lett. , 2004 , 14 , 4751 .
11.
Gutschow M.
, and
Neumann U.
, Bioorg. Med. Chem. , 1997 , 5 , 1935 .
12.
Brown D.A.
, and
Powers C. J.
, Bioorg. Med. Chem. , 1995 , 3 , 1091 .
13.
Davis S.J.
, and
Elvidge J. A.
, J. Chem. Soc. , 1962 , 3553 .
14.
Butt M.A.
,
Elvidge J. A.
, and
Foster A. B.
, J. Chem. Soc. , 1963 , 3069 .
15.
Al-Rawi J.M. A.
, and
Elvidge J. A.
, J. Chem. Soc. Perkin Trans. 1 , 1973 , 2432 .
16.
Al-Ajely M.S.
,
Busheer H. A.
, and
Abdul Ghnni A.
, National J. Chem. , 2007 , 26 , 348 .
17.
Khalilzadeh M.A.
,
Yavari I.
,
Hossaini Z.
, and
Sadeghifar H.
, Monatsh. Chem. , 2009 , 140 , 467 .
