Abstract
An efficient and environment-friendly method for the synthesis of 1,3-oxazine derivatives has been developed using the ultrasound-mediated condensation of 2-naphthol with formaldehyde and primary amines under solvent-free condition at room temperature in the presence of BF3-SiO2 to give the desired product in good to excellent yield. This procedure provides several advantages over current methods including a simple work-up, cost effectiveness, a reusable catalyst and shorter reaction times.
References
1.
Cravotto G.
, and
Cintas P.
, Chem. Soc. Rev. , 2006 , 35 , 180 .
2.
Arcadi A.
,
Alfonsi M.
, and
Mannelli F.
, Tetrahedron Lett. , 2009 , 50 , 2060 .
3.
Bretanha L.C.
,
Teixeira V.E.
,
Ritter M.
,
Siqueira G.M.
,
Cunico W.
,
Pereira C.M.P.
, and
Freitag R.A.
, Ultrason Sonochem. , 2011 , 18 , 704 .
4.
Wang S.X.
,
Li Z.Y.
,
Zhang J.C.
, and
Li J.T.
, Ultrason Sonochem. , 2008 , 15 , 677 .
5.
Wang Q.
, and
Pei W.
, J. Iran. Chem. Soc. , 2010 , 7 , 318 .
6.
Adib M.
,
Sheibani E.
, and
Mostofi M.
, Tetrahedron , 2006 , 62 , 3435 .
7.
Poel H.V.
,
Guilaumet G.
, and
Viaud-Massuard M.
, Tetrahedron Lett. , 2002 , 43 , 1205 .
8.
Buckman B.O.
,
Mohan R.
, and
Koovakkat S.
, Bioorg. Med. Chem. Lett. , 1998 , 8 , 2235 .
9.
Katsura Y.
,
Nishino S.
, and
Takasugi H.
, Chem. Pharm. Bull. , 1991 , 11 , 2937 .
10.
Joyce J.N.
,
Presgraves S.
, and
Renish L.
, Exp. Neurol. , 2003 , 184 , 393 .
11.
Higham C.S.
,
Dowling D.P.
,
Shaw J.L.
,
Cetin A.
,
Ziegler C.J.
, and
Farrell J.R.
, Tetrahedron Lett. , 2006 , 47 , 4419 .
12.
Burke W.J.
,
Glennie E.L.M.
, and
Weatherbee C.
, J. Org. Chem. , 1964 , 29 , 909 .
13.
Bijoy P.M.
,
Awanit K.
,
Satyasheel S.
,
Shukla P.K.
, and
Mahendra N.
, Eur. J. Med. Chem. , 2010 , 45 , 1502 .
14.
Bijoy P.M.
, and
Mahendra N.
, J. Heterocyclic Chem. , 2009 , 46 , 1003 .
15.
Suryakant B.S.
,
Kiran F.S.
,
Bapurao B.S.
, and
Murlidhar S.S.
, J. Korean Chem. Soci. , 2010 , 54 , 437 .
16.
Sadeghi B.
,
Mirjalili B.F.
, and
Hashemi M.M.
, Tetrahedron Lett. , 2008 , 49 , 2575 .
17.
Ramachandran R.
,
Jayanthi S.
, and
Jeong Y.T.
, Tetrahedron , 2011 , 68 , 363 .
18.
Dindulkar S.D.
,
Paramasivam P.
, and
Jeong Y.T.
, Monatsh Chem. , 2011 , 143 , 113 .
19.
Veeranarayana Reddy M.
,
Dindulkar S.D.
, and
Jeong Y.T.
, Tetrahedron Lett. , 2011 , 52 , 4764 .
20.
Veeranarayana Reddy M.
,
Jongsik K.
, and
Jeong Y.T.
J. Fluorine Chem. , 2012 , 135 , 155 .