Abstract
(Z)-2-(4-Halogenophenyl)-3-(thiophen-3-yl)acrylonitrile can be prepared by condensation of thiophene-3-carbaldehyde with arylacetonitrile halides in the presence of catalytic amounts of NaOCH3 at room temperature. Secondary arylamines reacted with (Z)-2-(4-halogenophenyl)-3-(thiophen-3-yl)acrylonitriles to afford thiophenylacrylonitrile derivatives containing a triphenylamine moiety on catalysis by Pd(OAc)2/P(o-tolyl)3 at 120°C in toluene. The UV-Vis absorption and photoluminescent (PL) spectra of the products in CH2Cl2were investigated.
References
1.
Amaresh M.
,
Ma C. Q.
, and
Peter B.
, Chem. Rev. , 2009 , 109 , 1141 .
2.
Frølund B.
,
Jensen L. S.
,
Storustovu S. I.
,
Stensbøl T. B.
,
Ebert B.
, and
Kehler J.
, J. Med. Chem. , 2007 , 50 , 1988 .
3.
Krovat E.M.
,
Frühwirth K. H.
, and
Langer T. J.
, Chem. Inf. Model , 2005 , 45 , 146 .
4.
Carpino L.A.
,
Abdel-Maksoud A. A.
,
Ionescu D.
,
Mansour E. M. E.
, and
Zewail M. A.
, J. Org. Chem. , 2007 , 72 , 1729 .
5.
Yoshimura H.
,
Nagai M.
,
Hibi S.
,
Kikuchi K.
,
Abe S.
,
Hida T.
,
Higashi S.
,
Hishinum I.
, and
Yamanaka T.
, J. Med. Chem. , 1995 , 38 , 3163 .
6.
Lee J.
, USP , 2006 , 135 , 488 .
7.
Zhu H.
,
Huang M.
,
Yang F.
,
Chen Y.
,
Miao Z. H.
,
Qian X. H.
,
Xu Y. F.
,
Qin Y. X.
,
Luo H. B.
,
Shen X.
,
Geng M. Y.
,
Cai Y. J.
, and
Ding J.
, Mol. Cancer. Therap. , 2007 , 6 , 484 .
8.
Xu Y.
,
Qu B.
,
Qian X.
, and
Li Y.
, Bioorg. Med. Chem. Lett , 2005 , 15 , 1139 .
9.
Tang M.L.
,
Toshihiro O.
, and
Bao Z. N.
, J. Am. Chem. Soc. , 2006 , 128 , 16002 .
10.
Tania A.
,
Adam C.
,
Simon J. C.
, and
Anna K. C.
, Macromolecules , 2009 , 42 , 2505 .
11.
Anthony C.
, and
Mary T. P.
, Inorg Chem. , 2008 , 47 , 10980 –10990 .
12.
Yamamoto T.
,
Nishiyama M.
, and
Koie Y.
, Tetrahedron Lett. , 1998 , 39 , 2367 .
13.
Thayumanavan S.
,
Barlow S.
, and
Marder S. R.
, Chem. Mater. , 1997 , 9 , 3231 .
14.
Ranasinghe M.I.
,
Varnavski O. P.
,
Pawlas J.
,
Hauck S. I.
,
Louie J.
,
Hartwig J. F.
, and
Goodson T.
, J. Am. Chem. Soc. , 2002 , 124 , 6520 .
15.
Chen C.
,
Li Y. F.
, and
Yang L. M.
, J. Mol. Catal A: Chem. , 2007 , 269 , 158 .
16.
Shirota Y.
, J. Mater. Chem. , 2005 , 15 , 75 .
17.
Thelakkat M.
, Macromol. Mater. Eng. , 2002 , 287 , 442 .
18.
Yu M.X.
,
Duan J. P.
,
Lin C. H.
,
Cheng C. H.
, and
Tao Y. T.
, Chem. Mater , 2002 , 14 , 3958 .
19.
Yu M.X.
,
Wen W. J.
, and
Chen C. H.
, Chin. J. Org. Chem. , 2006 , 26 , 1239 .
20.
Yu M.X.
,
Chang L. C.
,
Lin C. H.
,
Duan J. P.
,
Wu F. I.
, and
Chen I. C.
, Adv. Funct. Mater. , 2007 , 17 , 369 .
21.
Yu M.X.
,
Kang J. H.
, and
Chen C. H.
, Chin. J. Org. Chem. , 2008 , 8 , 1393 .
22.
Yue Y.F.
,
Fang H. Y.
,
Wang M. J.
,
Wang Z. Y.
, and
Yu M. X.
, J. Chem. Res. , 2009 , 6 , 377 .
23.
Goodbrand H.B.
, and
Hu N. X.
, J. Org. Chem. , 1999 , 64 , 670 .
24.
Yasuhiro Y.
,
Osaka-fu N. S.
, and
Kazuyos S. K.
, E.P. 1018505/2000.
25.
Kataoka N.
,
Shelby Q.
,
Stambuli J. P.
, and
Hartwig J. F.
, J. Org. Chem. , 2002 , 67 , 5553 .
26.
Vaccaro W.
,
Amore C.
,
Berger J.
,
Burrier R.
,
Clader J.
, and
Davis H.
, J. Med. Chem. , 1996 , 39 , 877 .
