Abstract
An efficient and facile one-pot, three-component protocol for the synthesis of pyrimido[4,5-b]quinoline-4-amines from the condensation of 2-aminoquinoline-3-carbonitrile, N,N-dimethylformamide dimethyl acetal and primary amines under microwave irradiation is reported. This efficient, straightforward procedure led to the desired products in high yields without the need for a catalyst or for a tandem addition–elimination–cyclisation reaction.
Keywords
References
1.
Zishiri V.K.
,
Joshi M.C.
,
Hunter R.
,
Chibale K.
,
Smith P.J.
,
Summers R.L.
,
Martin R.E.
, and
Egan T.J.
, J. Med. Chem. , 2011 , 54 , 6956 .
2.
Lilienkampf A.
,
Mao J.
,
Wan B.
,
Wang Y.H.
,
Franzblau S.G.
, and
Kozikowski A.P.
, J. Med. Chem. , 2009 , 52 , 2109 .
3.
Daoud R.
,
Desneves J.
,
Deady L.W.
,
Tilley L.
,
Scheper R.J.
,
Gros P.
, and
Georges E.
, Biochemistry , 2000 , 39 , 6094 .
4.
Rousseaux S.
,
Liégault B.
, and
Fagnou K.
, Chem. Sci. , 2012 , 3 , 244 .
5.
Huang H.
,
Jiang H.
,
Chen K.
, and
Liu H.
, J. Org. Chem. , 2009 , 74 , 5476 .
6.
Khalafi-Nezhad A.
,
Sarikhani S.
,
Shahidzadeh E.S.
, and
Panahi F.
, Green Chem. , 2012 , 14 , 2876 .
7.
Batey R.A.
, and
Powell D.A.
, Chem. Commun. , 2001 , 2362 .
8.
Bharate J.B.
,
Vishwakarma R.A.
, and
Bharate S.B.
, RSC Adv. , 2015 , 5 , 42020 .
9.
El-Gazzar A.B.A.
,
Hafez H.N.
, and
Nawwar G.A.M.
, Eur. J. Med. Chem. , 2009 , 44 , 1427 .
10.
Ali H.I.
,
Ashidab N.
, and
Nagamatsu T.
, Bioorg. Med. Chem. , 2008 , 16 , 922 .
11.
Joshi A.A.
, and
Viswanathan C.L.
, Bioorg. Med. Chem. Lett. , 2006 , 16 , 2613 .
12.
Tao Y.T.
,
Chuen C.H.
,
Ko C.W.
, and
Peng J.W.
, Chem. Mater. , 2002 , 14 , 4256 .
13.
Zhang X.Y.
,
Guo X.J.
, and
Fan X.S.
, Chem. Asian J. , 2015 , 10 , 106 .
14.
Singh R.M.
,
Sharma N.
,
Kumar R.
,
Asthana M.
, and
Upadhyay S.
, Tetrahedron , 2012 , 68 , 10318 .
15.
Wang K.
,
Herdtweck E.
, and
Dömling A.
, ACS Comb. Sci. , 2012 , 14 , 316 .
16.
Chandra A.
,
Upadhyay S.
,
Singh B.
,
Sharma N.
, and
Singh R.M.
, Tetrahedron , 2011 , 67 , 9219 .
17.
Boschelli D.H.
,
Powell D.
,
Golas J.M.
, and
Boschelli F.
, Bioorg. Med. Chem. Lett. , 2003 , 13 , 2977 .
18.
Wang D.L.
,
Zhou T.
,
Xing J.J.
,
Qian J.H.
, and
Liu L.
, Heterocycles , 2016 , 92 , 733 .
19.
Wang D.L.
,
Wang Y.Y.
,
Shi X.C.
, and
Ma J.
, Chin. Chem. Lett. , 2015 , 26 , 1109 .
20.
Wang D.L.
,
Wu J. Y.
,
Wu D.
, and
Wang Y.Y.
, Chin. Chem. Lett. , 2014 , 25 , 1555 .
21.
Rane B. S.
,
Kazi M.A.
,
Bagul S.M.
,
Shelar D.P.
,
Toche R.B.
, and
Jachak M.N.
, J. Fluoresc. , 2010 , 20 , 415 .