Abstract
The reaction of (Z)-2-amino-N‘-arylbenzamidines with both 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and 2,3,5,6-tetrachloro-1,4-benzoquinone have been studied. The reactions were carried at room temperature overnight in dry ethyl acetate and proceed via a charge transfer complexe to give dibenzo[b,e][1,4]diazepine derivatives in 35–44% yield. Benzodiazepine derivatives have anti-inflammatory, antiviral, antimicrobial, antileukaemic, antiplatelet, anticonvulsant, antianxiety, antidepressive and antitumour activities. The products were fully characterised according to their spectral analyses.
References
1.
Ramajazam R.
,
Giridhar R.
,
Yadav M.R.
,
Balaraman R.
,
Djaballah H.
,
Shum D.
, and
Radu C.
, Eur. J. Med. Chem. , 2008 , 43 , 2004 .
2.
Narayana B.
,
Vijaya Raj K.K.
,
Ashalatha B.V.
, and
Suchetha Kumari N.
, Eur. J. Med. Chem. , 2006 , 41 , 417 .
3.
DiBraccio M.
,
Grossi G.C.
,
Roma G.
,
Vargiu L.
,
Mura M.
, and
Marongiu M.E.
, Eur. J. Med. Chem. , 2001 , 36 , 935 .
4.
Kumar R.
, and
Joshi Y.C.
, Arkivoc , 2007 , xiii , 142 .
5.
Kamal A.
,
Shankaraiah N.
,
Prabhakar S.
,
Reddy C.R.
,
Markandeya N.
,
Laxma K.
, and
Devaiah X.
, Bioorg. Med. Chem. Lett. , 2008 , 18 , 2434 .
6.
Kosychova L.
,
Sumbrevicute Z.
,
Pleckaitiene L.
,
Janciene R.
, and
Puodziunaite B.D.
, Chem. Heterocycl. Comp. , 2004 , 40 , 811 .
7.
Janciene R.
,
Vektariene A.
,
Stumbreviciute Z.
,
Kochychova L.
, and
Klimavicius A.A.
, Heteroatom Chem. , 2004 , 15 , 363 .
8.
El-Shaieb K.M.
,
Hopf H.
, and
Jones P.G.
, Z. Naturforsch., Teil B , 2009 , 64 , 858 .
9.
El-Shaieb K.M.
, and
Jones P.G.
, Z. Naturforsch., Teil B. , 2009 , 64 , 945 .
10.
El-Shaieb K.M.
,
Hopf H.
, and
Jones P.G.
, Arkivoc , 2009 , x , 146 .
11.
El-Shaieb K.M.
,
Hopf H.
, and
Jones P.G.
, Arkivoc , 2010 , x , 98 .
12.
El-Shaieb K.M.
, J. Chem., Res. , 2010 , 137 .
13.
Abdel-latif F.F.
,
El-Shaieb K.M.
, and
El-Deen A.G.
, J. Chem. Res. , 2010 , 449 .
14.
Abdel-latif F.F.
,
El-Shaieb K.M.
, and
El-Deen A.G.
, J. Chem. Res. , 2010 , 699 .
15.
Abdel-latif F.F.
,
El-Shaieb K.M.
, and
El-Deen A.G.
, Z. Naturforsch., Teil B , 2011 , 66 , 965 .
16.
El-Shaieb K.M.
,
Hassan A.A.
, and
Mourad A.E.
, Heteroatom Chem. , 2004 , 15 , 63 .
17.
Aly A.A.
, and
El-Shaieb K.M.
, Tetrahedron , 2004 , 60 , 3797 .
18.
Aly A.A.
, and
El-Shaieb K.M.
, J. Chem. Res. , 2007 , 4 , 207 .
19.
Kalinowski H.-O.
,
Berger S.
, and
Braun S.
, 13C NMR Spektroskopie , Thieme ; Stuttgart , 1984 , 121 .
20.
Silverstein R.M.
, Spectrometric identification of organic compounds , John Wiley and Sons, Inc , New York , 1974 .
21.
Szczepankiewicz W.
, and
Suwin'ski J.
, Tetrahedron Lett. , 1998 , 39 , 1785 .
22.
Szczepankiewicz W.
,
Suwin'ski J.
, and
Bujok R.
, Tetrahedron , 2000 , 56 , 9343 .
23.
Gaber H.M.
,
Bagley M.C.
, and
Sherif S.M.
, Eur. J. Chem. , 2010 , 115 .
24.
Hassan A.A.
,
Mourad A.E.
,
El-Shaieb K.M.
,
Abou-Zied A.H.
, and
Döpp D.
, Heteroatom Chem. , 2003 , 14 , 535 .
