Abstract
1,4-Phenylenediamine reacted readily with chloroacetone to give 1,4-bis[(2-oxopropyl)amino]benzene which was used to prepare 1-(4-(1H-pyrrol-1-yl)phenyl)-1H-pyrrole derivatives in a one pot reaction with dimethylformamide dimethylacetal or triethyl orthoformate and an active methylene nitrile, an active methylene ketone or an ylidene-malononitrile. Reaction of 1,4-bis[(2-oxopropyl)amino]benzene with arene diazonium salts afforded the hydrazone derivatives which readily cyclised when reacted with malononitrile to give bispyrrole derivatives. The antibacterial activity of some of the products was determined.
References
1.
Minoshima M.
,
Chou J.C.
,
Lefebvre S.
,
Bando T.
,
Shinohara K.-i
,
Gottesfeld J.M.
, and
Sugiyama H.
, Bioorg. Med. Chem. , 2010 , 18 , 168 .
2.
Bennasroune A.
,
Gardin A.
,
Aunis D.
,
Cremel G.
, and
Hubert P.
, Crit. Rev. Oncol. Hematol. , 2004 , 50 , 23 .
3.
Moriarty K.J.
,
Koblish H.K.
,
Garrabrant T.
,
Maisuria J.
,
Khalil E.
,
Ali F.
,
Petrounia I.P.
,
Crysler C.S.
,
Maroney A.C.
,
Johnson D.L.
, and
Galemmo R.A.
, Bioorg. Med. Chem. Lett. , 2006 , 16 , 5778 .
4.
Ghorab M.M.
,
Ragab F.A.
,
Heiba H.I.
,
Youssef H.A.
, and
El-Gazzar M.G.
, Bioorg. Med. Chem. Lett. , 2010 , 20 , 6316
5.
Rosowsky A.
,
Chen H.
,
Fu H.
, and
Queener S. F
, Bioorg. Med. Chem. , 2003 , 11 , 59 .
6.
Choi H.S.
,
Wang Z.
,
Richmond W.
,
He X.
,
Yang K.
,
Jiang T.
,
Karanewsky D.
,
Gu X.J.
,
Zhou V.
,
Liu Y.
,
Che J.
,
Lee C.C.
,
Caldwell J.
,
Kanazawa T.
,
Umemura I.
,
Matsuura N.
,
Ohmori O.
,
Honda T.
,
Gray N.
, and
He Y.
, Bioorg. Med. Chem. Lett. , 2006 , 16 , 2689 .
7.
Morgan D.O.
, Can. J. Sci. Am. , 1998 , 4 , 1081 .
8.
Stefanachi A.
,
Nicolotti O.
,
Leonetti F.
,
Cellamare S.
,
Campagna F.
,
Loza M.I.
,
Brea J.M.
,
Mazza F.
,
Gavuzzo E.
, and
Carotti A.
, Bioorg. Med. Chem. , 2008 , 16 , 9780 .
9.
Sbardella G.
,
Mai A.
,
Artico M.
,
Loddo R.
,
Setzu M.G.
, and
Colla P.L.
, Bioorg. Med. Chem. Lett. , 2004 , 14 , 1537 .
10.
Padrón J.M.
,
Tejedor D.
,
Santos-Exposito A.
,
Garcia-Tellado F.
,
Martinc V.S.
, and
Villara J.
, Bioorg. Med. Chem. Lett. , 2005 , 15 , 2487 .
11.
Watanabe T.
,
Umezawa Y.
,
Takahashi Y.
, and
Akamatsu Y.
, Bioorg. Med. Chem. Lett. , 2010 , 20 , 5807 .
12.
Lee H.
,
Lee J.
,
Lee S.
,
Shin Y.
,
Jung W.
,
Kim J.-H.
,
Park K.
,
Kim K.
,
Cho H.S.
,
Ro S.
,
Lee S.
,
Jeong S.W.
,
Choi T.
,
Chung H.-H
, and
Koh J.S.
, Bioorg. Med. Chem. Lett. , 2001 , 11 , 3069 .
13.
Jiang C.
,
Yan J.
, and
Lin Y.
, Faming Zhuanli Shenqing Gongkai Shuomingshu , 2009 , [CN 101407486 A 20090415] http://worldwide.espacenet.com/publicationDetails/biblio?DB=EPODOC&II=0&ND=3&adjacent=true&locale=en_EP&FT=D&date=20090415&CC=CN&NR=101407486A&KC=A
14.
Al-Omran F.
,
Elassar A.A.
, and
El-khair A.A.
, J. Heterocycl. Chem. , 2003 , 40 , 249 .
15.
Fan A.-L.
,
Lin W.-H
, and
Jia Y.-X.
, J. Chin. Pharm. Sci. , 2011 , 20 , 425 .
16.
He-Ping L.
, Bioorg. Med. Chem. Lett. , 2006 , 16 , 6298 .
17.
Schweitzer B.A.
,
Loida P.J.
,
CaJacob C.A.
,
Chott R.C.
,
Collantes E.M.
,
Hegde S.G.
,
Mosier P.D.
, and
Profeta S.
, Bioorg. Med. Chem. Lett. , 2002 , 12 , 1743 .
18.
Umasankar Y.
,
Kumar S.A.
, and
Chen S.-M.
, Nanostruct. Mater. Electrochem. Biosen. , 2009 , 239 –259 .
19.
Yasui E.
,
Wada M.
, and
Takamura N.
, Tetrahedron Lett. , 2009 , 50 , 4762 .
20.
Rossi R.
, and
Bellina F.
, Tetrahedron , 2006 , 62 , 7213 .