Abstract
A number of 2-aryl-2H-chromene-4-carbonitriles were synthesised by cyanation of 2-aryl-3-nitro-2H-chromenes using trimethylsilyl cyanide (TMSCN) in the presence of tetrabutylammonium fluoride (TBAF) in moderate yields via a Michael addition/elimination pathway. The structures of all the products were characterised thoroughly by NMR, IR and HRMS spectroscopy and X-ray crystallographic analysis.
References
1.
Kitamura R.O.S.
,
Romoff P.
,
Young M.C.M.
,
Kato M.J.
, and
Lago J.H.G.
, Phytochemistry , 2006 , 67 , 2398 .
2.
Khafagy M.M.
,
El-Wahab A.H.F.A.
,
Eid F.A.
, and
El-Agrody A.M.
, Farmaco , 2002 , 57 , 715 .
3.
Liu H.-C.
,
Du L.
,
Zhu T.-J.
,
Li D.-H.
,
Geng M.-Y.
, and
Gu Q.-Q.
, Helv. Chim. Acta , 2010 , 93 , 2224 .
4.
Shaabani A.
,
Ghadari R.
,
Sarvary A.
, and
Rezayan A.H.
, J. Org. Chem. , 2009 , 74 , 4372 .
5.
Migani A.
,
Gentili P.L.
,
Negri F.
,
Olivucci M.
,
Romani A.
,
Favaro G.
, and
Becker R.S.
, J. Phys. Chem. A , 2005 , 109 , 8684 .
6.
Pina F.
,
Melo M.J.
,
Laia C.A.T.
,
Parola A.J.
, and
Lima J.C.
, Chem. Soc. Rev. , 2012 , 41 , 869 .
7.
Majumdar N.
,
Paul N.D.
,
Mandal S.
,
Bruin B.
, and
Wulff W.D.
, ACS Catal. , 2015 , 5 , 2329 .
8.
Rappoport Z.
, The chemistry of the cyano group. Wiley , New York , 1971 .
9.
Lindley J.
, Tetrahedron , 1984 , 40 , 1433 .
10.
Fontaine P.
,
Chiaroni A.
,
Masson G.
, and
Zhu J.P.
, Org. Lett. , 2008 , 10 , 1509 .
11.
Zang Y.
,
Zhang S.W.
,
Fu X.L.
,
Hu X.L.
,
Ren D.M.
, and
Li X.F.
, J. Chem. Res. , 2017 , 41 , 614 .
12.
Zhang S.W.
,
Fu X.L.
,
Ren D.M.
,
Li X.F.
,
Yang L.L.
, and
Yu X.Y.
, J. Chem. Res. , 2017 , 41 , 517 .
13.
Fu X.L.
,
Ren D.M.
,
Li X.F.
, and
Hu X.L.
, J. Chem. Res. , 2017 , 41 , 420 .
14.
Fu X.L.
,
Li H.T.
,
Ren D.M.
, and
Li X.F.
, J. Chem. Res. , 2017 , 41 , 709 .
15.
Yan M.C.
,
Jang Y.J.
,
Kuo W.Y.
,
Tu Z.
,
Shen K.H.
,
Cuo T.S.
,
Ueng C.H.
, and
Yao C.F.
, Heterocycles , 2002 , 57 , 1033 .
16.
Galano J.J.
,
Alias M.
,
Perez R.
,
Velázquez-Campoy A.
,
Hoffman P.S.
, and
Sancho J.R.
, J. Med. Chem. , 2013 , 56 , 6248 .
17.
Liu S.X.
,
Jia C.M.
,
Yao B.Y.
,
Chen X.L.
, and
Zhang Q.
, Synthesis , 2016 , 48 , 407 .
18.
Fu Z.K.
,
Pan J.Y.
,
Xu D.C.
, and
Xie J.W.
, RSC Adv. , 2014 , 4 , 51548 .
19.
Jiang W.
,
Sun J.
, and
Yan C. G.
, RSC Adv. , 2017 , 7 , 42387 .
20.
Samira R.N.
,
Maliheh S.
,
Mahboobeh P.
,
Kabudanian A.S.
,
Leila K.
,
Yaghoub P.
,
Mohammad M.
,
Saeed E.
,
Alireza F.
, and
Abbas S.
, Eur. J. Med. Chem. , 2014 , 86 , 562 .
