Abstract
2-Cyano-3-nitroporphyrin derivatives were synthesised by the reaction of 2-nitroporphyrin with trimethylsilyl cyanide in the presence of tetrabutylammonium fluoride with moderate yields. The reaction took place regioselectively on the 3-position carbon of the porphyrins, which was confirmed by X-ray analysis.
References
1.
Giraudeau A.
,
Callot H.J.
,
Jordan J.
,
Ezhar I.
, and
Gross M.
, J. Am. Chem. Soc. , 1979 , 101 , 3857 .
2.
Baldwin J.E.
,
Crossley M.J.
, and
DeBernardis J.
, Tetrahedron , 1982 , 38 , 685 .
3.
Crossley M.J.
,
Harding M.M.
, and
Tansey C.W.
, J. Org. Chem. , 1994 , 59 , 4433 .
4.
Crossley M.J.
,
King L.G.
, and
Simpson J.L.
, J. Chem. Soc., Perkin Trans. 1 , 1997 , 3087 .
5.
Giuntini F.
,
Faustino M.A.F.
,
Neves M.G.P.M.S.
,
Tomé A.C.
,
Silva A.M.S.
, and
Cavaleiro J.A.S.
, Tetrahedron , 2005 , 61 , 10454 .
6.
Lacerda P.S.S.
,
Silva A.M.G.
,
Tomé A.C.
,
Neves M.G.P.M.S.
,
Silva A.M.S.
,
Cavaleiro J.A.S.
, and
Llamas-Saiz A.L.
, Angew. Chem., Int. Ed. , 2006 , 45 , 5487 .
7.
Yang L.L.
,
Li X.F.
,
Hu X.L.
, and
Yu X.Y.
, Tetrahetron. Lett. , 2016 , 57 , 1265 .
8.
Yang L.L.
,
Hu X.L.
,
Tang Z.Q.
, and
Li X.F.
, Chem. Lett. , 2015 , 44 , 1515 .
9.
Wang C.-H.
, and
Kingsbury C.A.
, J. Org. Chem. , 1975 , 40 , 3811 .
10.
Murahashi S.
,
Naota T.
, and
Saito E.
, J. Am. Chem. Soc. , 1986 , 108 , 7846 .
11.
Aizencang G.
,
Frydman R.B.
,
Giorgieri S.
,
Guerra L.
, and
Frydman B.
, J. Med. Chem. , 1995 , 38 , 4337 .
12.
Soli E.D.
,
Manoso A.S.
,
Patterson M.C.
, and
DeShong P.
, J. Org. Chem. , 1999 , 64 , 3171 .
13.
Li X.F.
,
Meng Y.K.
,
Yi P.G.
,
Stępień M.
, and
Chmielewski P.J.
, Angew. Chem. Int. Ed. , 2017 , 56 , 10810 .
14.
Liu B.
,
Yoshida T.
,
Li X.F.
,
Stepien M.
,
Shinokubo H.
, and
Chmielewski P.J.
, Angew. Chem. Int. Ed. , 2016 , 55 , 13142 .
15.
Li X.F.
,
Liu B.
,
Yi P.G.
,
Yi R.Q.
,
Yu X.Y.
, and
Chmielewski P.J.
, J. Org. Chem. , 2011 , 76 , 2345 .
16.
Liu B.
,
Li X.F.
,
Stępień M.
, and
Chmielewski P.J.
, Chem. Eur. J. , 2015 , 21 , 7790 .
17.
Liu B.
,
Fang H.Y.
,
Li X.F.
,
Cai W.T.
,
Bao L.P.
,
Rudolf M.
,
Plass F.
,
Fan L.Z.
,
Lu X.
, and
Guldi D.M.
, Chem. Eur. J. , 2015 , 21 , 746 .
18.
Liu B.
,
Li X.F.
,
Maciołek J.
,
Stępień M.
, and
Chmielewski P.J.
, J. Org. Chem. , 2014 , 79 , 3129 .
19.
Deng Z.H.
,
Li X.F.
,
Stępień M.
, and
Chmielewski P.J.
, Chem. Eur. J. , 2016 , 22 , 4231 .
20.
Liu B.
,
Li X.F.
,
Xu X.
,
Stępień M.
, and
Chmielewski P.J.
, J. Org. Chem. , 2013 , 78 , 1354 .
