Abstract
2,6-Bis[1-(pyridin-2-yl)-1H-benzo[d]-imidazol-2-yl]pyridine (bpbp), which has been synthesised by intramolecular thermocyclisation of N2,N6-bis[2-(pyridin-2-ylamino)phenyl]pyridine-2,6-dicarboxamide, reacts with sodium pyridine-2,6-dicarboxylate (pydic) and RuCl3 to give [Ru(bpbp)(pydic)] which can catalyse the oxidation of (1H-benzo[d]imidazol-2-yl)methanol to 1H-benzo[d]imidazole-2-carbaldehyde by H2O2. The optimal reaction conditions were: molar ratios of catalyst to substrate to H2O2 set at 1: 1000: 3000; reaction temperature 50 °C; reaction time 5 h. The yield of (1H-benzo[d]imidazol-2-yl) methanol was 70%.
Keywords
References
1.
Kim M.K.
,
Shin H.
,
Park K.
,
Kim H.
,
Park J.
,
Kim K.
,
Nam J.
,
Choo H.
, and
Chong Y.
, J. Med. Chem. , 2015 , 58 , 7596 .
2.
Lombardy R.L.
,
Tanious F.A.
,
Ramachandran K.
,
Tidwell R.R.
, and
Wilson W. Da.
, J. Med. Chem. , 1996 , 39 , 1452 .
3.
Yan W.
,
Wang X.
,
Dai Y.
,
Zhao B.
,
Yang X.
,
Fan J.
,
Gao Y.
,
Meng F.
,
Wang Y.
,
Luo C.
,
Ai J.
,
Geng M.
, and
Duan W.
, J. Med. Chem. , 2016 , 59 , 6690 .
4.
Han W.
,
Ding Y.
,
Xu Y.
,
Pfister K.
,
Zhu S.
,
Warne B.
,
Doyle M.
,
Aikawa M.
,
Amiri P.
,
Appleton B.
,
Stuart D.D.
,
Fanidi A.
, and
Shafer C.M.
, J. Med. Chem. , 2016 , 59 , 3034 .
5.
Chen B.T.
,
Morlanés N.
,
Adogla E.
,
Takanabe K.
, and
Rodionov V.O.
, ACS Catal. , 2016 , 6 , 4647 .
6.
Semwal S.
, and
Choudhury J.
, ACS Catal. , 2016 , 6 , 2424 .
7.
Yellol J.
,
Pérez S.A.
,
Buceta A.
,
Yellol G.
,
Donaire A.
,
Szumlas P.
,
Bednarski P.J.
,
Makhloufi G.
,
Janiak C.
,
Espinosa A.
, and
Ruiz J.
, J. Med. Chem. , 2015 , 58 , 7310 .
8.
Islamoglu T.
,
Behera S.
,
Kahveci Z.
,
Tessema T.D.
,
Jena P.
, and
El-Kaderi H.M.
, ACS Appl. Mater. Interfaces , 2016 , 8 , 14648 .
9.
Dubey K.C. Ravi
, and
Balaji B.
, Indian J. Chem., Sect B , 2003 , 42 , 3128 .
10.
Li J.
,
Hu Q.
,
Yu X.
,
Zeng Y.
,
Cao C.
,
Liu X.
,
Guo J.
, and
Pan Z.
, J. Fluoresc. , 2011 , 21 , 2005 .
11.
Ramaiah K.
,
Dubey P.K.
,
Ramaniham J.
,
Kumar C.R.
, and
Grossert J.S.
, Indian J. Chem., Sect. B , 2003 , 42 , 1765 .
12.
Hong Chin O.
, and
Hans S.
, J. Chem. Soc., Perkin Trans. I , 1982 , 12 , 2871 .
13.
Bahrini C.
,
Herbinet O.
,
Glaude P.A.
,
Schoemaecker C.
,
Fittschen C.
, and
Battin-Leclerc F.
, J. Am. Chem. Soc. , 2012 , 134 , 11944 .
14.
Le Maux P.
, and
Simonneaux G.
, Chem. Commun. , 2011 , 47 , 6957 .
15.
Kotlewska A.J.
,
van Rantwijk F.
,
Sheldon R.A.
, and
Arends I.W.C.E.
, Green Chem. , 2011 , 13 , 2154 .
16.
Egami H.
,
Oguma T.
, and
Katsuki T.
, J. Am. Chem. Soc. , 2010 , 132 , 5886 .
17.
Murahashi S.I.
, Ruthenium in organic synthesis , Wiley-VCH , Weinheim , 2004 .
18.
Liu S.G.
,
Zuo J.L.
,
Li Y. Z
, and
You X.Z.
, J. Mol. Struct. , 2004 , 705 , 153 .
19.
Liu S.G.
,
Zuo J.L.
,
Wang Y.
,
Li Y.Z.
, and
You X.Z.
, J. Phys. Chem. Solids , 2005 , 66 , 735 .
20.
Liu S.G.
,
Zhang L.P.
,
Liu J.
,
Su W.Y.
, and
Shi X. B.
, Spectrochim. Acta A : 2012 , 97 , 464 .
21.
Liu S.G.
,
Cao W.Q.
,
Yu L.L.
,
Zheng W.J.
,
Li L.L.
,
Fan C.D.
, and
Chen T.F.
, Dalton Trans. , 2013 , 42 , 5932 .
22.
Liu S.G.
,
Zhou X.T.
, and
Ji H.B.
, Catal. Commun. , 2013 , 37 , 60 .
23.
Zhou X.T.
,
Ji H.B.
, and
Liu S.G.
, Tetrahedron Lett. , 2013 , 543882 .
24.
Tse M.K.
,
Bhor S.
,
Klawonn M.
,
Anilkumar G.
,
Jiao H.
,
Döber C.
,
Spannenberg A.
,
Mägerlein W.
,
Hugl H.
, and
Beller M.
, Chem. Eur. J. , 2006 , 12 , 1855 .
25.
Stephenson A.
, and
Warburton W.K.
, J. Chem. Soc. C , 1970 , 1355 .
26.
Liu S.G.
,
Liu W.
,
Li Y.Z.
, and
You X.Z.
, Chin. J. Inorg. Chem. , 2005 , 21 , 543 .
27.
Takizawa S.
,
Montes V.A.
, and
Anzenbacher P.
Jr.
, Chem. Mater. , 2009 , 21 , 2452 .
