Abstract
An iodobenzene-catalysed domino route to quinoxalines from ketones and o-phenylenediamines in one pot has been developed. This transformation consisted of the generation of Koser's generation, α-tosyloxylation of ketones, nucleophilic substitution and intramolecular dehydration with o-phenylenediamines, and dehydrogenation.
References
1.
Lindsley C.W.
,
Zhao Z.J.
,
Leister W.H.
,
Robinson R.G.
,
Barnett S.F.
,
Defeo-Jones D.
,
Jones R.E.
,
Hartman G.D.
,
Huff J.R.
,
Huber H.E.
, and
Duggan M.E.
, Bioorg. Med. Chem. Lett. , 2005 , 15 , 761 .
2.
Jaso A.
,
Zarranz B.
,
Aldana I.
, and
Monge A.
, Chem. J. Med. Chem. , 2005 , 48 , 2019 .
3.
Thomas K.R.J.
,
Velusamy M.
,
Lin J.T.
,
Chuen C.H.
, and
Tao Y.T.
, Chem. Mater. , 2005 , 17 , 1860 .
4.
Dailey S.
,
Feast J.W.
,
Peace R.J.
,
Age I.C.
,
Till S.
, and
Wood E.L.J.
, Mater. Chem. , 2001 , 11 , 2238 .
5.
Cho C.S.
, and
Oh S.G.
, J. Mol. Catal., A: Chem. , 2007 , 276 , 205 .
6.
Meshram H.M.
,
Ramesh P.
,
Santosh G.K.
, and
Reddy B.C.
, Tetrahedron Lett. , 2010 . 51 , 4313 .
7.
Huang T.Q.
,
Zhang Q.
,
Chena J.X.
,
Gao W.X.
,
Ding J.C.
, and
Wu H.Y.
, J. Chem. Res. , 2009 . 12 , 761 .
8.
Krishnakumar B.
,
Velmurugan R.
,
Jothivel S.
, and
Swaminathan M.
, Catal. Commun. , 2010 , 11 , 997 .
9.
Venkatesh C.
,
Singh B.
,
Mahata P.K.
, and
Junjappa H.
, Org. Lett. , 2005 , 7 , 2169 .
10.
More S.V.
,
Sastry M.N.V.
,
Wang C.C.
, and
Yao C.F.
, Tetrahedron Lett. , 2005 , 46 , 6345 .
11.
Bhosale R.S.
,
Sarda S.R.
,
Ardhapure S.S.
,
Jadhav W.N.
,
Bhusare S.R.
, and
Pawar R.P.
, Tetrahedron Lett. , 2005 , 46 , 7183 .
12.
Chung C.L.
,
Han C.H.
,
Wang H.M.
,
Hou R.S.
, and
Chen L.C.
, J. Chinese Chem. Soc. (Taiwan) , 2009 , 56 , 683 .
13.
Padmavathy K.
,
Nagendrappa Gopalpur
, and
Geetha K.V.
, Tetrahedron Lett. , 2011 , 52 , 544 .
14.
Xu X.S.
,
Deng Y.
,
Li X.Q.
,
Zhao Z.T.
,
Fang W.Y.
, and
Yan X.H.
, J. Chem. Res. , 2011 , 10 , 605 .
15.
Yamamoto Y.
, and
Togo H.
, Synlett. , 2006 , 798 .
16.
Rodriguez A.
, and
Moran W.J.
, Org. Lett. , 2011 , 13 , 2220 .
17.
Yamamoto Y.
,
Kawano Y.
,
Toy P.H.
, and
Togo H.
, Tetrahedron , 2007 , 63 , 4680 .
18.
Zhang C.
,
Xu Z.J.
,
Zhang L.G.
, and
N. J
, Tetrahedron , 2012 , 68 , 5258 .
19.
Kumar B.S.P.A.
,
Madhav B.
,
Reddy K.H.V.
, and
Nageswar Y.V.D.
, Tetrahedron Lett. , 2011 , 52 , 2862 .