Abstract
A facile one-pot, four-component reaction for the synthesis of pyrrolo[1,2-a]quinolines is described. Knoevenagel condensation reaction of malononitrile and aromatic aldehydes gave 2-arylmethylidenemalononitriles which on treatment with quinoline and cyclohexyl isocyanide under solvent-free conditions afforded 1-(cyclohexylamino)-2-arylpyrrolo[1,2-a]quinoline-3-carbonitriles in good yields.
References
1.
Brandi A.
, and
Cicchi S.
, Comprehensive heterocyclic chemistry III , eds
Katritzky A.R.
,
Ramsden C.A.
,
Scriven E.F.V.
, and
Taylor R.J.K.
Elsevier Science , Oxford , 2008 , Vol. 11 , pp. 368 –401 .
2.
Flitsch W.
, in: Comprehensive heterocyclic chemistry II , eds
Katritzky A.R.
,
Rees C.W.
, and
Scriven E.F.V.
Pergamon Press , New York , 1996 , Vol. 8 , pp. 237 –248 .
3.
El-Sayed I.I.
, and
El-Sayed H.E.A.
, Adv. Heterocycl. Chem. , 2003 , 84 , 71 .
4.
Wei L.L.
,
Hsung R.P.
,
Sklenicka H.M.
, and
Gerasyuto A.I.
, Angew. Chem., Int. Ed. Engl. , 2001 , 40 , 1516 .
5.
Santarem M.
,
Vanucci-Bacqué C.
, and
Lhommet G.
, J. Org. Chem. , 2008 , 73 , 6466 .
6.
Bertram H.J.
,
Fisher R.
,
Hagemarm H.
,
Krueger B.W.
,
Shenke T.
,
Erdelen C.
,
Krauskopf B.
,
Luerssen K.
, and
Santel H.J.
, Ger. Pat. , 4,032,090 A1, 1991 .
7.
Duerr H.
,
Joensson H.P.
,
Spang P.
,
Muenzmay T.
, and
Scheihauer P.
, Ger. Pat. , 3,521,432 Al, 1986 .
8.
Oguchi Y.
,
Katagiri K.
, and
Takasu Y.
, Jap. Pat. , 61,108,593, 1986 .
9.
Katagiri K.
,
Ognchi Y.
,
Otake T.
,
Arao K.
, and
Takasu Y.
, Jap. Pat. , 6,115,148, 1986 .
10.Mitsubishi Paper Mills Ltd. , Jap. Pat. , 60,121,440, 1985 .
11.
Tanaka A.
,
Nakatani M.
, and
Yoshida A.
, US Pat. , 77,120,824, 1979 .
12.
Hazra A.
,
Mondal S.
,
Maity A.
,
Naskar S.
,
Saha P.
,
Paira R.
,
Sahu K.B.
,
Paira P.
,
Ghosh S.
,
Sinha C.
,
Samanta A.
,
Banerjee S.
, and
Mondal N.B.
, Eur. J. Med. Chem. , 2011 , 46 , 2132 .
13.
Chernyak D.
,
Gadamsetty S.B.
, and
Gevorgyan V.
, Org. Lett. , 2008 , 10 , 2307 .
14.
Liu Y.
,
Song Z.
, and
Yan B.
, Org. Lett. , 2007 , 9 , 409 .
15.
Hulcoop D.G.
, and
Lautens M.
, Org. Lett. , 2007 , 9 , 1761 .
16.
Mironov M.A.
,
Mokrushin V.S.
, and
Maltsev S.S.
, Synlett , 2003 , 943 .
17.
Li M.
,
Qiu Z.X.
,
Wen L.R.
, and
Zhou Z.M.
, Tetrahedron , 2011 , 67 , 3638 .
18.
Li M.
,
Lv X.L.
,
Wen L.R.
, and
Hu Z.Q.
, Org. Lett. , 2013 , 15 , 1262 .
19.
Marandi G.
,
Habibi-Khorassani S.M.
,
Hazeri N.
,
Maghsoodlou M.T.
,
Akbarzadeh Torbati N.
,
Rostami-Charati F.
,
Makha M.
, and
Skelton B.W.
, J. Heterocycl. Chem. , 2013 , 50 , 568 .
20.
Yavari I.
,
Aminkhani A.
, and
Skoulika S.
, J. Iran. Chem. Soc. , 2013 , 10 , 107 .
21.
Aminkhani A.
, Heterocycl. Commun. , 2013 , 19 , 109 .
22.
Adib M.
,
Sheikhi E.
,
Bijanzadeh H.R.
, and
Zhu L.G.
, Tetrahedron , 2012 , 68 , 3377 .
23.
Adib M.
,
Sheikhi E.
,
Bagheri M.
,
Bijanzadeh H.R.
, and
Amanlou M.
, Tetrahedron , 2012 , 68 , 3237 .
24.
Adib M.
,
Sheikhi E.
, and
Rezaei N.
, Tetrahedron Lett. , 2011 , 52 , 3191 .
25.
Adib M.
,
Ansari S.
, and
Bijanzadeh H.R.
, Synlett , 2011 , 619 .
