Abstract
A facile synthesis of novel 7-alkynylindazole derivatives involving the Pd/C–PPh3–CuI catalysed Sonogashira coupling of 7-iodoindazole with a wide range of terminal alkynes in aqueous medium is reported. An X-ray crystallographic study established the molecular structure of 7-(pent-1-ynyl)-1H-indazole.
References
1.
Upadhyay A.
,
Srivastava S.K.
,
Srivastava S.D.
, and
Yadav R.
, Ind. J. Chem. , 2011 , 50-B , 89 .
2.
Minami M.
,
Endo T.
,
Tamakai H.
,
Ogawa T.
,
Hamaue N.
,
Hirafuji M.
,
Monma Y.
,
Yoshioka M.
, and
Hagihara K.
, Eur. J. Pharmaco. , 1997 , 321 (3 ), 333 .
3.
Maggio B.
,
Raimondi M.V.
,
Raffa D.
,
Plescia F.
,
Casscioferro S.
,
Plescia S.
,
Tolomeo M.
,
Cristina A.D.
,
Pipitone R.M.
,
Grimaudo S.
, and
Daidone G.
, Eur. J. Med. Chem. , 2011 , 46 , 168 .
4.
Lee F.Y.
,
Lien J.C.
,
Huang L.J.
,
Huang T.M.
,
Tsai S.C.
,
Teng C.M.
,
Wu C.C.
,
Cheng F.C.
, and
Kuo S.C.
, J. Med. Chem. , 2001 , 44 , 3746 .
5.
Silverstrini B.
, and
Baiocchi L.
, UK patent GB2110532.
6.
Salvatore P.
,
Demetrio R.
,
Fabiana P.
, and
Giovanni C.
,
Benedetta M.
,
Giuseppe D.
,
Maria V.R.
,
Maria G.C.
,
Gabriella B.
, and
Fiorella M.
, ARKIVOC , 2010 , X , 163 .
7.
Fludzinski P.
,
Evrard D.A.
,
Bloomquist W.E.
,
Lacefield W.B.
,
Pfeifer W.
,
Jones N.D.
,
Deeter J.B.
, and
Cohen M.L.
, J. Med. Chem. , 1987 , 30 , 1535 .
8.
Cottyn B.
,
Vichard D.
,
Terrier F.
,
Nioche P.
, and
Raman C.S.
, Synlett , 2007 , 8 , 1203 .
9.
Cottyn B.
,
Acher F.
,
Ramassamy B.
,
Alvey L.
,
Lepoivre M.
,
Frapart Y.
,
Stuehr D.
,
Mansuy D.
,
Boucher J.
, and
Vichard D.
, Bioorg. Med. Chem. , 2008 , 16 , 5962 .
10.
Bouissane L.
,
Kazzouli S.E.
,
Léonce S.
,
Peiffer B.
,
Rakib E.M.
,
Khouili M.
, and
Gullaumet G.
, Bioorg. Med. Chem. , 2006 , 14 , 1078 .
11.
Soodamani V.
,
Patel D.
,
Nayakanti D.
, and
Josyula R.
, J. Heterocycl. Chem. , in press.
12.
Robert F.
WO2010127855.
13.
MaheshKumar P.
,
Sivakumar K.
,
SrinivasReddy P.
,
Mohakhud P.K.
,
Mukkanti K.
, and
Pal M.
, Tetrahedron Lett. , 2011 , 52 , 1187 .