Abstract
A novel way to synthesise 2-aryl-4H-benzo[d][1,3]oxazin-4-ones has been developed by the cyclisation of Schiff bases with (diacetoxyiodo)benzene. The salient features of this new protocol which starts from an anthranilic acid and an aromatic aldehyde, are short reaction time, mild reaction conditions and good yields.
References
1.
Hsieh P.W.
,
Yu H.P.
,
Chang Y.J.
, and
Hwang T.L.
, Eur. J. Med. Chem. , 2010 , 45 , 3111 .
2.
Shreder K.R.
,
Cajica J.
,
Du L.
,
Fraser A.
,
Hu Y.
,
Kohno Y.
,
Lin E.C.K.
,
Liu S.J.
,
Okerberg E.
,
Pham L.
,
Wu J.
, and
Kozarich J.W.
, Bioorg. Med. Chem. Lett. , 2009 , 19 , 4743 .
3.
Hsieh P.W.
,
Hwang T.L.
,
Wu C.C.
,
Chang F.R.
,
Wang T.W.
, and
Wu Y.C.
, Bioorg. Med. Chem. Lett. , 2005 , 15 , 2786 .
4.
Powers J.C.
,
Asgian J.L.
,
Ekici O.D.
, and
James K.E.
, Chem. Rev. , 2002 , 102 , 4639 .
5.
Teshima T.
,
Griffin J.C.
, and
Powers J.C.
, J. Biol. Chem. , 1982 , 257 , 5085 .
6.
Kalusa A.
,
Chessum N.
, and
Jones K.
, Tetrahedron Lett. , 2008 , 49 , 5840 .
7.
Kashaw S.K.
,
Kashaw V.
,
Mishra P.
,
Jain N.K.
, and
Stables J.P.
, Eur. J. Med. Chem. , 2009 , 44 , 4335 .
8.
Georgios R.
,
Athanasios K.
, and
George V.
, Tetrahedron , 2011 , 67 , 7805 .
9.
Salvadori J.
,
Balducci E.
,
Zaza S.
,
Petricci E.
, and
Taddei M.
, J. Org. Chem. , 2010 , 75 , 1841 .
10.
Zhdankin V.V.
, and
Stang P.J.
, Chem. Rev. , 2008 , 108 , 5299 .
11.
Svensson P.H.
, and
Kloo L.
, Chem. Rev. , 2003 , 103 , 1649 .
12.
Fujioka H.
,
Komatsu H.
,
Miyoshi A.
,
Murai K.
, and
Kita Y.
, Tetrahedron Lett. , 2011 , 52 , 973 .
13.
Katrun P.
,
Chiampanichayakul S.
,
Korworapan K.
,
Pohmakotr M.
,
Reutrakul V.
,
Jaipetch T.
, and
Kuhakarn C.
, Eur. J. Org. Chem. , 2010 , 5633 .
14.
Hiromichi F.
,
Hideyuki K.
,
Taeko N.
,
Akihito M.
,
Kayoko H.
,
Jnashuara G.
,
Kenichi M.
, and
Yasuyuki K.
, Chem. Commun. , 2010 , 46 , 4113 .
15.
Qian W.X.
,
Erlei J.
,
Bao W.L.
, and
Zhang Y.M.
, Tetrahedron , 2006 , 62 , 556 .
16.
Singh S.
, and
Tripathi O.P.
, Acta Cienc. Indica, Chem. , 2006 , 32 , 249 .
17.
Papadopoulos E.P.
, and
Torres C.D.
, Heterocycles , 1982 , 19 , 1039 .
18.
Yadav M.R.
,
Shirude S.T.
,
Parmar A.
,
Balaraman R.
, and
Giridhar R.
, Chem. Heterocycl. Compd , 2006 , 42 , 1038 .
19.
Arfan M.
,
Khan R.
,
Imran M.
,
Khan H.
, and
Mehmood J.
, J. Chem. Soc. Pa k. , 2008 , 30 , 299 .
20.
Desai D.R.
,
Patel V.S.
, and
Patel S.R.
, J. Indian Chem. Soc. , 1966 , 43 , 351 .