Abstract
A synthesis in good to excellent yields of 23 4H-benzo[d][1,3]oxazin-4-ones, 18 of which are novel, from monosubstituted anthranilic acids and variously substituted phenyl isoselenocyanates without using any harsh reagents has been developed. The Se powder precipitated during the reaction could be efficiently recycled for the preparation of the aryl isoselenocyanates.
References
1.
Krantz A.
,
Spencer R.W.
,
Tam T.F.
,
Liak T.J.
,
Copp L.J.
,
Tomas E.M.
, and
Rafferty S.P.
, J. Med. Chem. , 1990 , 33 , 464 .
2.
Kakuta H.
,
Koiso Y.
,
Takahashi H.
,
Nagasawa K.
, and
Hashimoto Y.
, Heterocycles , 2001 , 55 , 1433 .
3.
Abdel Fattah M.E.
,
Abdel Gawad I.I.
, and
Mina S.M.
, Egypt. J. Chem. , 2006 , 49 , 651 .
4.
Kakuta H.
,
Tanatani A.
,
Nagasawa K.
, and
Hashimoto Y.
, Chem. Pharm. Bull. , 2003 , 51 , 1273 .
5.
Kashaw S.K.
,
Kashaw V.
,
Mishra P.
,
Jain N.K.
, and
Stables J.P.
, Eur. J. Med. Chem. , 2009 , 44 , 4335 .
6.
Rotas G.
,
Kimbaris A.
, and
Varvounis G.
, Tetrahedron , 2011 , 67 , 7805 .
7.
Shreder K.R.
,
Cajica J.
,
Du L.L.
,
Fraster A.
,
Hu Y.
,
Kohno Y.
,
Lin E.C.K.
,
Liu S.J.
,
Okerberg E.
,
Pham L.
,
Wu J.Y.
, and
Kozarich J.W.
, Bioorg. Med. Chem. Lett. , 2009 , 19 , 4743 .
8.
Kalusa A.
,
Chessum N.
, and
Jones K.
, Tetrahedron. Lett. , 2008 , 49 , 5840 .
9.
Garin J.
,
Melendez E.
,
Merchan F.L.
,
Tejero T.
, and
Villarroya E.
, Synthesis , 1983 , 406 .
10.
Molina P.
,
Aller E.
,
Ecija M.
, and
Lorenzo A.
, Synthesis , 1996 , 690 .
11.
Fernández-Bolaños J.G.
,
López Ó.
,
Ulgar V.
,
Maya I.
, and
Fuentes J.
, Tetrahedron Lett. , 2004 , 45 , 4081 .
12.
Sommen G.L.
,
Linden A.
, and
Heimgartner H.
, Eur. J. Org. Chem. , 2005 , 3128 .
13.
Garud D.R.
,
Makimura M.
,
Ando H.
,
Ishihara H.
, and
Koketsu M.
, Tetrahedron Lett. , 2007 , 48 , 7764 .
14.
Garud D.R.
, and
Koketsu M.
, Org. Lett. , 2008 , 10 , 3319 .
15.
Garud D.R.
,
Toyoda Y.
, and
Koketsu M.
, Tetrahedron Lett. , 2009 , 50 , 3035 .
16.
Sommen G.L.
,
Linden A.
, and
Heimgartner H.
, Tetrahedron , 2006 , 62 , 3344 .
17.
Garud D.R.
,
Koketsu M.
, Org. Lett. , 2008 , 10 , 3319 .
18.
Xie Y. Y.
,
Liu J.L.
,
Yang P.
,
Shi X.J.
, and
Li J.J.
, Tetrahedron , 2011 , 67 , 5369 .
19.
Papadopoulos E.P.
, and
Torres C.D.
, J. Heterocycl. Chem. , 1982 , 19 , 269 .
20.
Jung S.H.
,
Ahn J.H.
,
Park S.K.
, and
Choi J.K.
, Bull. Korean Chem. Soc. , 2002 , 23 , 149 .
21.
Su W.K.
, and
Liang X.R.
, J. Indian Chem. Soc. , 2003 , 80 , 645 .