在含水介质中钯高效催化咪唑并[1,2-a]吡啶类化合物与芳基氯代物的碳氢芳基化反应（英文）
|
摘要
3-芳基咪唑并[1,2-a]吡啶骨架广泛存在于药物结构中,在药物学方面具有重要的地位及在材料化学、有机化学等方面也具有潜在的应用价值.在含水介质中,利用醋酸钯催化咪唑并[1,2-a]吡啶及其衍生物与芳基/杂芳基氯代物的碳氢芳基化反应,简便、高效地合成系列3-芳基咪唑并[1,2-a]吡啶类化合物,并以较好至优秀的收率获得芳基化产品.该方法采用廉价易得的芳基/杂芳基氯代物和咪唑并[1,2-a]吡啶类化合物为偶联反应的底物,且底物的范围能够拓展至缺电子、富电子的芳基氯代物和杂芳基氯代物及多种基团取代的咪唑并[1,2-a]吡啶类化合物.
An efficient and practical protocol for palladium-catalyzed direct C—H bond arylation of imidazo[1,2-a]pyridines with cheap aryl/heteroaryl chlorides has been developed. Various imidazo[1,2-a]pyridines with electron-neutral, electron-poor, electron-rich, even sterically hindered aryl chlorides and heteroaryl chlorides were successfully applied to the reaction in aqueous medium to achieve the 3-arylimidazo[1,2-a]pyridines in mostly good to excellent yields, thus representing a significant advancement in the implementation of the direct C—H bond arylation of imidazo[1,2-a]pyridines with aryl chlorides.
An efficient and practical protocol for palladium-catalyzed direct C—H bond arylation of imidazo[1,2-a]pyridines with cheap aryl/heteroaryl chlorides has been developed. Various imidazo[1,2-a]pyridines with electron-neutral, electron-poor, electron-rich, even sterically hindered aryl chlorides and heteroaryl chlorides were successfully applied to the reaction in aqueous medium to achieve the 3-arylimidazo[1,2-a]pyridines in mostly good to excellent yields, thus representing a significant advancement in the implementation of the direct C—H bond arylation of imidazo[1,2-a]pyridines with aryl chlorides.
引文
[1]Bagdi,A.K.;Santra,S.;Monir,K.;Hajra,A.Chem.Commun.2015,51,1555.
[2]Moraski,G.C.;Markley,L.D.;Hipskind,P.A.;Boshoff,H.;Cho,S.;Franzblau,S.G.;Miller,M.J.ACS Med.Chem.Lett.2011,2,466.
[3]Egner,U.;Gerbling,K.P.;Hoyer,G.A.;Krüger,G.;Wegner,P.Pestic.Sci.1996,47,145.
[4]Bae,J.S.;Lee,D.W.;Lee,D.H.;Jeong,D.S.WO 2007011163,2007[Chem.Abstr.2007,146,193485].
[5]El-Sayed,W.M.;Hussin,W.A.;Al-Faiyz,Y.S.;Ismail,M.A.Eur.J.Pharmacol.2013,715,212.
[6]Lacerda,R.B.;de Lima,C.K.F.;da Silva,L.L.;Romeiro,N.C.;Miranda,A.L.P.;Barreiro,E.J.;Fraga,C.A.M.Bioorg.Med.Chem.2009,17,74.
[7]Shukla,N.M.;Salunke,D.B.;Yoo,E.;Mutz,C.A.;Balakrishna,R.;David,S.A.Bioorg.Med.Chem.2012,20,5850.
[8]Ismail,M.A.;Arafa,R.K.;Wenzler,T.;Brun,R.;Tanious,F.A.;Wilson,W.D.;Boykin,D.W.Bioorg.Med.Chem.2008,16,683.
[9]Véron,J.B.;Allouchi,H.;Enguehard-Gueiffier,C.;Snoeck,R.;Andrei,G.;De Clercq,E.;Gueiffier,A.Bioorg.Med.Chem.2008,16,9536.
[10]Kaminski,J.J.;Doweyko,A.M.J.Med.Chem.1997,40,427.
[11]Rival,Y.;Grassy,G.;Taudon,A.;Ecalle,R.Eur.J.Med.Chem.1991,26,13.
[12]Enguehard-Gueiffier,C.;Musiu,S.;Henry,N.;Véron,J.B.;Mavel,S.;Neyts,J.;Leyssen,P.;Paeshuyse,J.;Gueiffier,A.Eur.J.Med.Chem.2013,64,448.
[13]Patel,H.S.;Linn,J.A.;Drewry,D.H.;Hillesheim,D.A.;Zuercher,W.J.;Hoekstra,W.J.Tetrahedron Lett.2003,44,4077.
[14]Liu,G.P.;Cong,X.F.;He,J.H.;Luo,S.Z.;Wu,D.;Lan,J.B.J.Chem.Res.2012,36,687.
[15]Wu,Z.Q.;Pan,Y.Y.;Zhou,X.G.Synthesis 2011,2255.
[16]Dixon,L.I.;Carroll,M.A.;Gregson,T.J.;Ellames,G.J.;Harrington,R.W.;Clegg,W.Org.Biomol.Chem.2013,11,5877.
[17]Collins,M.R.;Huang,Q.;Ornelas,M.A.;Scales,S.A.Tetrahedron Lett.2010,51,3528.
[18]Monir,K.;Bagdi,A.K.;Ghosh,M.;Hajra,A.Org.Lett.2014,16,4630.
[19]Enguehard,C.;Renou,J.L.;Collot,V.;Hervet,M.;Rault,S.;Gueiffier,A.J.Org.Chem.2000,65,6572.
[20]Marhadour,S.;Bazin,M.A.;Marchand,P.Tetrahedron Lett.2012,53,297.
[21]Nandi,D.;Jhou,Y.M.;Lee,J.Y.;Kuo,B.C.;Liu,C.Y.;Huang,P.W.;Lee,H.M.J.Org.Chem.2012,77,9384.
[22]Karale,U.B.;Kalari,S.;Shivakumar,J.;Makane,V.B.;Babar,D.A.;Thakare,R.P.;Nagendra Babu,B.;Chopra,S.;Rode,H.B.RSC Adv.2016,6,65095.
[23]Mu,B.;Wu,Y.S.;Li,J.Y.;Zou,D.P.;Chang,J.B.;Wu,Y.J.Org.Biomol.Chem.2016,14,246.
[24]Lee,J.;Chung,J.;Byun,S.M.;Kim,B.M.;Lee,C.Tetrahedron2013,69,5660.
[25]Fu,H.Y.;Chen,L.;Doucet,H.J.Org.Chem.2012,77,4473.
[26]Nandi,D.;Siwal,S.S.;Mallick,K.Chemistry Select 2017,2,1747.
[27]Cao,H.;Zhan,H.Y.;Lin,Y.G.;Lin,X.L.;Du,Z.D.;Jiang,H.F.Org.Lett.2012,14,1688.
[28]Kalari,S.;Babar,D.A.;Karale,U.B.;Makane,V.B.;Rode,H.B.Tetrahedron Lett.2017,58,2818.
[29]Choy,P.Y.;Luk,K.C.;Wu,Y.N.;So,C.M.;Wang,L.L.;Kwong,F.Y.J.Org.Chem.2015,80,1457.
[30]Cao,H.;Lin,Y.G.;Zhan,H.Y.;Du,Z.D.;Lin,X.L.;Liang,Q.M.;Zhang,H.RSC Adv.2012,2,5972.
[31]Liu,Q.X.;He,B.Y.;Qian,P.C.;Shao,L.X.Org.Biomol.Chem.2017,15,1151.
[32]Zhao,G.K.;Zhang,K.N.;Wang,L.;Li,J.Y.;Zou,D.P.;Wu,Y.J.;Wu,Y.S.Tetrahedron Lett.2015,56,6700.
[33]Ke,C.H.;Kuo,B.C.;Nandi,D.;Lee,H.M.Organometallics2013,32,4775.
[34]Frett,B.;Mc Connell,N.;Smith,C.C.;Wang,Y.X.;Shah,N.P.;Li,H.Y.Eur.J.Med.Chem.2015,94,123.
[35]Hiebel,M.A.;Fall,Y.;Scherrmann,M.C.;Berteina-Raboin,S.Eur.J.Org.Chem.2014,2014,4643.
[36]Cooper,K.;Fray,M.J.;Parry,M.J.;Richardson,K.;Steele,J.J.Med.Chem.1992,35,3115.
[2]Moraski,G.C.;Markley,L.D.;Hipskind,P.A.;Boshoff,H.;Cho,S.;Franzblau,S.G.;Miller,M.J.ACS Med.Chem.Lett.2011,2,466.
[3]Egner,U.;Gerbling,K.P.;Hoyer,G.A.;Krüger,G.;Wegner,P.Pestic.Sci.1996,47,145.
[4]Bae,J.S.;Lee,D.W.;Lee,D.H.;Jeong,D.S.WO 2007011163,2007[Chem.Abstr.2007,146,193485].
[5]El-Sayed,W.M.;Hussin,W.A.;Al-Faiyz,Y.S.;Ismail,M.A.Eur.J.Pharmacol.2013,715,212.
[6]Lacerda,R.B.;de Lima,C.K.F.;da Silva,L.L.;Romeiro,N.C.;Miranda,A.L.P.;Barreiro,E.J.;Fraga,C.A.M.Bioorg.Med.Chem.2009,17,74.
[7]Shukla,N.M.;Salunke,D.B.;Yoo,E.;Mutz,C.A.;Balakrishna,R.;David,S.A.Bioorg.Med.Chem.2012,20,5850.
[8]Ismail,M.A.;Arafa,R.K.;Wenzler,T.;Brun,R.;Tanious,F.A.;Wilson,W.D.;Boykin,D.W.Bioorg.Med.Chem.2008,16,683.
[9]Véron,J.B.;Allouchi,H.;Enguehard-Gueiffier,C.;Snoeck,R.;Andrei,G.;De Clercq,E.;Gueiffier,A.Bioorg.Med.Chem.2008,16,9536.
[10]Kaminski,J.J.;Doweyko,A.M.J.Med.Chem.1997,40,427.
[11]Rival,Y.;Grassy,G.;Taudon,A.;Ecalle,R.Eur.J.Med.Chem.1991,26,13.
[12]Enguehard-Gueiffier,C.;Musiu,S.;Henry,N.;Véron,J.B.;Mavel,S.;Neyts,J.;Leyssen,P.;Paeshuyse,J.;Gueiffier,A.Eur.J.Med.Chem.2013,64,448.
[13]Patel,H.S.;Linn,J.A.;Drewry,D.H.;Hillesheim,D.A.;Zuercher,W.J.;Hoekstra,W.J.Tetrahedron Lett.2003,44,4077.
[14]Liu,G.P.;Cong,X.F.;He,J.H.;Luo,S.Z.;Wu,D.;Lan,J.B.J.Chem.Res.2012,36,687.
[15]Wu,Z.Q.;Pan,Y.Y.;Zhou,X.G.Synthesis 2011,2255.
[16]Dixon,L.I.;Carroll,M.A.;Gregson,T.J.;Ellames,G.J.;Harrington,R.W.;Clegg,W.Org.Biomol.Chem.2013,11,5877.
[17]Collins,M.R.;Huang,Q.;Ornelas,M.A.;Scales,S.A.Tetrahedron Lett.2010,51,3528.
[18]Monir,K.;Bagdi,A.K.;Ghosh,M.;Hajra,A.Org.Lett.2014,16,4630.
[19]Enguehard,C.;Renou,J.L.;Collot,V.;Hervet,M.;Rault,S.;Gueiffier,A.J.Org.Chem.2000,65,6572.
[20]Marhadour,S.;Bazin,M.A.;Marchand,P.Tetrahedron Lett.2012,53,297.
[21]Nandi,D.;Jhou,Y.M.;Lee,J.Y.;Kuo,B.C.;Liu,C.Y.;Huang,P.W.;Lee,H.M.J.Org.Chem.2012,77,9384.
[22]Karale,U.B.;Kalari,S.;Shivakumar,J.;Makane,V.B.;Babar,D.A.;Thakare,R.P.;Nagendra Babu,B.;Chopra,S.;Rode,H.B.RSC Adv.2016,6,65095.
[23]Mu,B.;Wu,Y.S.;Li,J.Y.;Zou,D.P.;Chang,J.B.;Wu,Y.J.Org.Biomol.Chem.2016,14,246.
[24]Lee,J.;Chung,J.;Byun,S.M.;Kim,B.M.;Lee,C.Tetrahedron2013,69,5660.
[25]Fu,H.Y.;Chen,L.;Doucet,H.J.Org.Chem.2012,77,4473.
[26]Nandi,D.;Siwal,S.S.;Mallick,K.Chemistry Select 2017,2,1747.
[27]Cao,H.;Zhan,H.Y.;Lin,Y.G.;Lin,X.L.;Du,Z.D.;Jiang,H.F.Org.Lett.2012,14,1688.
[28]Kalari,S.;Babar,D.A.;Karale,U.B.;Makane,V.B.;Rode,H.B.Tetrahedron Lett.2017,58,2818.
[29]Choy,P.Y.;Luk,K.C.;Wu,Y.N.;So,C.M.;Wang,L.L.;Kwong,F.Y.J.Org.Chem.2015,80,1457.
[30]Cao,H.;Lin,Y.G.;Zhan,H.Y.;Du,Z.D.;Lin,X.L.;Liang,Q.M.;Zhang,H.RSC Adv.2012,2,5972.
[31]Liu,Q.X.;He,B.Y.;Qian,P.C.;Shao,L.X.Org.Biomol.Chem.2017,15,1151.
[32]Zhao,G.K.;Zhang,K.N.;Wang,L.;Li,J.Y.;Zou,D.P.;Wu,Y.J.;Wu,Y.S.Tetrahedron Lett.2015,56,6700.
[33]Ke,C.H.;Kuo,B.C.;Nandi,D.;Lee,H.M.Organometallics2013,32,4775.
[34]Frett,B.;Mc Connell,N.;Smith,C.C.;Wang,Y.X.;Shah,N.P.;Li,H.Y.Eur.J.Med.Chem.2015,94,123.
[35]Hiebel,M.A.;Fall,Y.;Scherrmann,M.C.;Berteina-Raboin,S.Eur.J.Org.Chem.2014,2014,4643.
[36]Cooper,K.;Fray,M.J.;Parry,M.J.;Richardson,K.;Steele,J.J.Med.Chem.1992,35,3115.