Abstract
The regiospecific 1,4-Michael addition of phenylacetonitrile to (2E,4E)-1,5-diarylpenta-2,4-dien-1-ones produced 12 novel (E)-3-(2-oxo-2-arylethyl)-2,5-diarylpent-4-enenitriles in 77-88% yield. The advantages of the method are broad substrate scope, mild conditions, good to high yields and high selectivity. The method can also be extended to a gram scale.
References
1.
Cao D.D.
,
Fang G.S.
,
Zhang J.X.
,
Wang H.Y.
,
Zheng C.W.
, and
Zhao G.
, J. Org. Chem. , 2016 , 81 , 9973 .
2.
Zhang S.Y.
,
Ruan G.Y.
,
Geng Z.C.
,
Li N.K.
,
Lv M.
,
Wang Y.
, and
Wang X.W.
, Org. Biomol. Chem. , 2015 , 13 , 5698 .
3.
Nayak S.
,
Chakroborty S.
,
Bhakta S.
,
Panda P.
, and
Mohapatra S.
, Res. Chem. Intermed. , 2016 , 42 , 2731 .
4.
Fernandez G.
,
de Troconiz A.
,
Ochoa de Retana
,
Pascual S.
,
Ezpeleta J.M.
, and
Palacios F.
, Eur. J. Org. Chem. , 2013 , 2013 , 5614 .
5.
Surowiec M.
,
Belekos D.
,
Makosza M.
, and
Varvounis G.
, Eur. J. Org. Chem. , 2010 , 2010 , 3501 .
6.
Xing F.
,
Feng Z.N.
,
Wang Y.
,
Du G.F.
,
Gu C.Z.
,
Dai B.
, and
He L.
, Adv. Synth. Catal. , 2018 , 360 , 1704 .
7.
Liu C.H.
,
Xu Y.L.
,
Niu S.Y.
,
Wei L.Q.
,
Liu Y.
,
Wang Y.B.
,
Zhu J.Y.
,
Fu J.Y.
, and
Yuan J.F.
, Chin. J. Chem. , 2017 , 35 , 1231 .
8.
Li X.
,
Yang C.
,
Jin J.L.
,
Xue X.S.
, and
Cheng J.P.
, Chem. Asian J. , 2013 , 8 , 997 .
9.
Luo X.Y.
,
Wang L.L.
,
Peng L.
,
Bai J.F.
,
Jia L.N.
,
Tian F.
,
Xu X.Y.
, and
Wang L.X.
, Chin. J. Chem. , 2012 , 30 , 2703 .
10.
Wu B.
,
Liu G.G.
,
Li M.Q.
,
Zhang Y.
,
Zhang S.Y.
,
Qiu J.R.
,
Xu X.P.
,
Ji S.J.
, and
Wang X.W.
, Chem. Commun. , 2011 , 47 , 3992 .
11.
Li Z.
,
Li J.S.
,
Fu R.G.
,
Xie D.M.
,
Song G.Y.
,
Song W.L.
, and
Yang J.Y.
, J. Heterocycl. Chem. , 2017 , 54 , 3410 .
12.
Moulia A.
,
Teo J.
,
Johannes C.W.
, and
Richard J.A.
, RSC Adv. , 2013 , 3 , 22882 .
13.
Song G.Y.
, and
Li Z.
, Chem. Pap. , 2018 , 72 , 1379 .
14.
Gu X.D.
,
Guo T.T.
,
Dai Y.Y.
,
Franchino A.
,
Fei J.
,
Zou C.C.
,
Dixon D.J.
, and
Ye J.X.
, Angew. Chem. Int. Ed. , 2015 , 54 , 10249 .
15.
Oliva C.G.
,
Silva A.M.S.
,
Paz F.A.A.
, and
Cavaleiro J.A.S.
, Synlett , 2010 , 2010 , 1123 .
16.
Kowalczyk R.
, and
Boratynski P.J.
, Adv. Synth. Catal. , 2016 , 358 , 1289 .
17.
Brocchini S.J.
, and
Lawton R.G.
, Tetrahedron Lett. , 1997 , 38 , 6319 .
18.
Li Z.
,
Li T.P.
,
Fu R.G.
, and
Yang J.Y.
, Heterocycl. Commun. , 2017 , 23 , 287 .
19.
Lear M.J.
, and
Hayashi Y.
, ChemCatChem , 2013 , 5 , 3499 .
20.
Xin Y.
,
Zang Z.H.
, and
Chen F.L.
, Synth. Commun. , 2009 , 39 , 4062 .
