Abstract
N1-substituted octahydro-1H-pyrano[2,3-d]pyrimidines derivatives were prepared in moderate yield by the reaction of methyl [(4aRS,5SR,10aRS)-5-aryl-2-oxo-3,4,4a,10a-tetrahydro-2H,5H-pyrano[3,2-e][1,3]thiazolo[3,2-a]pyrimidin-8(9H)-ylidene]acetate and 2,6-dichorobenzonitrile oxide via a domino 1,3-dipolar cycloaddition/ring-opening/dethionation process. The structures of the products were characterised by spectroscopic and X-ray crystallographic analysis.
References
1.
Gangjee A.
,
Vasudevan A.
,
Queener S.F.
, and
Kisliuk R.L.
, J. Med. Chem. , 1996 , 39 , 1438 .
2.
Kappe O.
, Tetrahedron , 1993 , 49 , 6937 .
3.
Vuppalapati S.V.N.
,
Lingaiah R.B.
, and
Kantevari S.
, J. Heterocyclic Chem. , 2010 , 47 , 687 .
4.
Zhu Y.L.
,
Huang S.L.
,
Wan J.P.
,
Yan L.
,
Pan Y.J.
, and
Wu A.X.
, Org. Lett. , 2006 , 8 , 2599 .
5.
Bhattacharya R.N.
,
Kundu P.
, and
Maiti G.
, Tetrahedron Lett. , 2011 , 52 , 26 .
6.
Yu G.J.
,
Iwamoto S.
,
Robins L.I.
,
Fettinger J.C.
,
Sparks T.C.
,
Lorsbach B.A.
, and
Kurth M.J.
, J. Agric. Food Chem. , 2009 , 57 , 7422 .
7.
Sun R.F.
,
Li Y.Q.
,
Xiong L.X.
,
Liu Y.X.
, and
Wang Q.M.
, J. Agric. Food Chem. , 2011 , 59 , 4851 .
8.
Poutiainen P.K.
,
Oravilahti T.
,
Peräkylä M.
,
Palvimo J.J.
,
Ihalainen J.A.
,
Laatikainen R.
, and
Pulkkinen J.T.
, J. Med. Chem. , 2012 , 55 , 6316 .
9.
Li X.F.
,
Yi R.
,
Liu B.
,
Zheng A.T.
,
Yu X.Y.
, and
Yi P.G.
, J. Heterocyclic Chem. , 2014 , 51 , 274 .
10.
Li X.F.
,
Yu X.Y.
, and
Yi P.G.
, Chin J. Chem. , 2010 , 28 , 434 .
11.
Kozurkova M.
,
Sabolova D.
,
Janovec L.
,
Mikes J.
,
Koval J.
,
Ungvarsky J.
,
Stefanisinova M.
,
Fedorocko P.
,
Kristian P.
, and
Imrich J.
, Bioorg. Med. Chem. , 2008 , 16 , 3976 .
12.
Ling Y.L.
,
Liu H.C.
,
Zheng A.T.
,
Li G.B.
, and
Li X.F.
, J. Heterocyclic Chem. , 2013 , 50 , 1009 .
13.
Yao F.
,
Zeng R.J.
,
Wang H.
, and
Shen P.F.
, J. Hunan Univ. Sci. & Technol. (Nat. Sci. Ed.) , 2011 , 26 . 101 .
14.
Grundmann C.
, and
Dean J.M.
, J. Org. Chem. , 1965 , 30 , 2809 .