Abstract
A mild and efficient method for the synthesis of 7-aryl-9-methyl-3H- pyrazolo[4,3-f]quinoline derivatives via a three-component reaction of an aromatic aldehyde, 1H-indazol-5-amine and acetone catalysed by iodine is described. This new procedure has the advantages of mild reaction conditions, high yields and a metal-free catalyst.
References
1.
Danel A.
,
Gondek E.
, and
Kityk I.
, Opt. Mater. , 2009 , 32 , 267 .
2.
Khachatryan K.
,
Boszczyk W.
, and
Tomasik P.
, Polish J. Chem. , 2005 , 79 , 1645 .
3.
Luszczynska B.
,
Dobruchowska E.
,
Glowacki I.
,
Ulanski J.
,
Jaiser F.
,
Yang X.
,
Neher D.
, and
Danel A.
, J. Appl. Phy. , 2006 , 99 , 024505/1.
4.
Gondek E.
,
Kityk I.V.
,
Sanetra J.
,
Szlachcic P.
,
Armatys P.
,
Wisla A.
, and
Danel A.
, Opt. Laser Technol. , 2006 , 38 , 487 .
5.
Gondek E.
,
Kityk I.V.
,
Danel A.
,
Wisla A.
, and
Sanetra J.
, Synth. Metals , 2006 , 156 , 1348 .
6.
Al-Qahtani A.
,
Siddiqui Y.M.
,
Bekhit A.A.
,
El-Sayed O.A.
,
Aboul-Enein H.Y.
, and
Al-Ahdal M.N.
, Arch. Pharm. 2005 , 338 , 484 .
7.
Vartale S.P.
,
Jadhav J.S.
,
Kale M.A.
, and
Kuberkar S.V.
, Indian J. Heterocycl. Chem. , 2006 , 16 , 163 .
8.
Hays D.S.
,
Prince R.B.
,
Haraldson C.A.
, and
Bonk J.D.
, PCT Int. Appl. WO 2006107851 A1 12 Oct 2006, 152pp. Chem. Abstr. , 2006 , 145 , 419133 .
9.
Merrill B.A.
,
Danielson M.E.
,
Hays D.S.
,
Amos D.T.
,
Heppner P.D.
,
Kshirsagar T.A.
,
Lundquist G.D.
, and
Moser W.H.
, PCT Int. Appl. WO 2006107771 A2 12 Oct 2006, 135pp. Chem. Abstr. , 2006 , 145 , 419140 .
10.
Colotta V.
,
Catarzi D.
,
Varano F.
,
Capelli F.
,
Lenzi O.
,
Filacchioni G.
,
Martini C.
,
Trincavelli L.
,
Ciampi O.
,
Pugliese A.M.
,
Pedata F.
,
Schiesaro A.
,
Morizzo E.
, and
Moro S.
, J. Med. Chem. , 2007 , 50 , 4061 .
11.
Colotta V.
,
Capelli F.
,
Lenzi O.
,
Catarzi D.
,
Varano F.
,
Poli D.
,
Vincenzi F.
,
Varani K.
,
Borea P.A.
,
Dal Ben D.
,
Volpini R.
,
Cristalli G.
, and
Filacchioni G.
, Bioorg. Med. Chem. , 2009 , 17 , 401 .
12.
Malleshwar D.
,
Gautami K.
, and
Jayashree A.
, Org. Chem: An Indian J. , 2009 , 5 , 344 .
13.
Mali J.R.
,
Pratap U.R.
,
Jawale D.V.
, and
Mane R.A.
, Tetrahedron Lett. , 2010 , 51 , 3980 .
14.
Tu S.-J.
,
Wu S.-S.
,
Zhang X.-H.
,
Han Z.-G.
,
Cao X.-D.
, and
Hao W.-J.
, Synth. Commun. , 2010 , 40 , 1057 .
15.
Duggineni S.
,
Sawant D.
,
Saha B.
, and
Kundu B.
, Tetrahedron , 2006 , 62 , 3228 .
16.
Jachak M.N.
,
Avhale A.B.
,
Medhane V.J.
, and
Toche R.B.
, J. Heterocycl. Chem. , 2006 , 43 , 1169 .
17.
Cho C.-H.
,
Neuenswander B.
,
Lushington G.H.
, and
Larock R.C.
, J. Comb. Chem. , 2009 , 11 , 900 .
18.
Zeng L-H.
, and
Cai C.
, J. Comb. Chem. , 2010 , 12 , 35 .
19.
Das B.
,
Balasubramanyam P.
,
Krishnaiah M.
,
Veeranjaneyulu B.
, and
Reddy G.C.
, J. Org. Chem. , 2009 , 74 , 4393 .
20.
Wang G.-W.
, and
Gao J.
, Org. Lett. , 2009 , 11 , 2385 .
21.
Mal D.
, and
De S.R.
, Org. Lett. , 2009 , 11 , 4398 .
22.
Parvatkar P.T.
,
Parameswaran P.S.
, and
Tilve S.G.
, J. Org. Chem. , 2009 , 74 , 8369 .
23.
Wang X.S.
,
Li Q.
,
Wu J.R.
, and
Tu S.J.
, J. Comb. Chem. , 2009 , 11 , 433 .
24.
Wang X.S.
,
Li Q.
,
Yao C.S.
, and
Tu S.J.
, Eur. J. Org. Chem. , 2008 , 3513 .
25.
Povarov L.S.
, Russ. Chem. Rev. , 1967 , 36 , 656 .
26.
Kouznetsov V.V.
, Tetrahedron , 2009 , 65 , 2721 .
27.
Lin X.F.
,
Cui S.L.
, and
Wang Y.G.
, Tetrahedron Lett. , 2006 , 47 , 3127 .
