过渡金属催化合成胍类衍生物研究进展
收稿日期: 2016-04-18
修回日期: 2016-05-16
网络出版日期: 2016-06-20
基金资助
海南省自然科学基金（Nos.20162015，20152027）、海南省国际科技合作专项（No.KJHZ2014-02）、教育部高等学校博士学科点专项科研基金（No.20134601110004）资助项目.
Recent Advances in Transition Metal-Catalyzed Synthesis of Guanidines
Received date: 2016-04-18
Revised date: 2016-05-16
Online published: 2016-06-20
Supported by
Project supported by the Natural Science Fundation of Hainan Province (Nos.20162015, 20152027), the Hainan Province International Science and Technology Specific (No.KJHZ2014-02) and the Research Fund for the Doctoral Program of Higher Education of China (No.20134601110004).
胍（R1NHC（=NR2）NHR3）为一类独特的三氮化合物，其结构单元广泛存在于天然产物和药物分子中.他们具有多样性生物活性，在药物和农药领域都有广泛应用；此外，其在有机合成和功能材料领域也有很高的应用价值.由于胍独特的结构和广泛的应用价值，其合成方法的研究已成为有机合成研究的一个热点.近年来不断有胍的新合成方法涌现，特别是高效的过渡金属催化合成方法.本文主要对近20年来发展的过渡金属催化构筑C-N键反应合成胍类化合物的方法进行综述，全面介绍各类胍化合物合成方法的研究现状，总结归纳不同过渡金属催化合成方法的规律、特点及不足，为过渡金属催化合成胍类化合物的研究提供帮助.
徐树英 , 陈小佳 , 黎吉辉 , 许文茸 , 张玉苍 . 过渡金属催化合成胍类衍生物研究进展[J]. 有机化学, 2016 , 36(9) : 1985 -1993 . DOI: 10.6023/cjoc201604036
Guanidines are a unique class of tri-nitrogen compounds having various bioactivities, which are wildly presented in natural products and drug molecules, and they are wildly used in pharmacy and pesticide fields. Moreover, they have high application value in organic synthesis and functional materials. The synthesis of guanidines has received much attention due to their unique structures and widespread application value. Recently, lots of new synthetic methods of guanidines, especially the synthetic methods based on highly efficient transition metal-catalyzed reactions, have been developed. The recent progress in transition metal-catalyzed reactions developed for the synthesis of guanidines in the past twenty years is summarized. The synthetic methods for various guanidines are introduced comprehensively, and the characteristics and disadvantages of these methods are also discussed, thus it may be helpful for the research on transition metal-catalyzed synthesis of guanidines.
[1] Tapiero,H.;Mathé,G.;Couvreur,P.;Tew,K.D.Biomed.Pharmacother.2002,56,439.
[2] (a) Heys,L.;Moore,C.G.;Murphy,P.J.Chem.Soc.Rev.2000,29,57. (b) Urban,S.;Leone,P.A.;Carroll,A.R.;Fechner,G.A.;Smith,J.;Hooper,J.N.A.;Quinn,R.J.J.Org.Chem.1999,64,731. (c) Hensler,M.E.;Bernstein,G.;Nizeta,V.;Nefzi,A.Bioorg.Med.Chem.Lett.2006,16,5073. (d) Masuda,T.;Shibuya,S.;Arai,M.;Yoshida,S.;Tomozawa,T.;Ohno,A.;Yamashitab,M.;Honda,T.Bioorg.Med.Chem.Lett.2003,13,669.
[3] Selig,P.Synthesis 2013,45,703.
[4] Karmel,I.S.R.;Fridman,N.;Tamm,M.;Eisen,M.S.J.Am.Chem.Soc.2014,136,17180.
[5] (a) Cao,Y.-J.;Gao,H.-X.;Lu,R.-H.Chin.J.Synth.Chem.2003,11,193(in Chinese). (曹玉娟,高海翔,鲁润华,合成化学,2003,11,19.) (b) Shen,Z.-X.;Wang,Y.-L.;Zhang,Y.-W.Chin.J.Org.Chem.2002,22,388(in Chinese). (沈宗旋,王亚玲,张雅文,有机化学,2002,22,388.) (c) Ma,Y.;De,S.;Chen,C.Tetrahedron 2015,71,1145.
[6] (a) Ni,C.;Zhu,L.;Hu,J.Acta Chem.Sinica 2015,73,90(in Chinese). (倪传法,朱林桂,胡金波,化学学报,2015,73,90.) (b) Zhang,W.;Dai,J.;Xu,H.Chin.J.Org.Chem.2015,35,1820(in Chinese). (张文曼,戴建军,许华建,有机化学,2015,35,1820.)
[7] Lu,B.;Li,X.;Lin,Y.Chin.J.Org.Chem.2015,35,2275(in Chinese). (卢贝丽,李现艳,林咏梅,有机化学,2015,35,2275.)
[8] Tan,M.;Gu,Y.;Luo,X.;Zhang,P.Chin.J.Org.Chem.2015,35,781(in Chinese). (谭明雄,顾运琼,罗旭健,张培,有机化学,2015,35,781.)
[9] Qin,Y.;Peng,Q.Chin.J.Org.Chem.2011,31,1169(in Chinese). (秦元成,彭强,有机化学,2011,31,1169.)
[10] (a) Xie,J.;Zhou,Q.Acta Chem.Sinica 2012,70,1427(in Chinese). (谢建华,周其林,化学学报,2012,70,1427.) (b) Zhao,Y.;Guo,C.;Wu,H.Prog.Chem.2014,26,345(in Chinese). (赵艳,郭彩红,武海顺,化学进展,2014,26,345.)
[11] (a) Zhuo,Z.;Wang,T.;Zhou,X.;Zhang,H.Chin.J.Org.Chem.2014,34,1471(in Chinese). (卓庆德,王铜道,周小茜,张弘,有机化学,2014,34,1471.) (b) Liao,G.;Shi,B.Acta Chim.Sinica 2015,73,1283(in Chinese). (廖港,史炳锋,化学学报,2015,73,1283.)
[12] Cortes-Salva,M.;Nguyen,B.-L.;Cuevas,J.;Pennypacker,K.R.;Antilla,J.C.Org.Lett.2010,12,1316.
[13] Xing,H.;Zhang,Y.;Lai,Y.;Jiang,Y.;Ma,D.J.Org.Chem.2012,77,5449.
[14] Miyabe,H.;Yoshida,K.;Reddy,V.K.;Takemoto,Y.J.Org.Chem.2009,74,305.
[15] (a) Zhong,M.;Bui,M.;Shen,W.;Baskaran,S.;Allen,D.A.;Elling,R.A.;Flanagan,W.M.;Fung,A.D.;Hanan,E.J.;Harris,S.O.;Heumann,S.A.;Hoch,U.;Ivy,S.N.;Jacobs,J.W.;Lam,S.;Lee,H.;McDowell,R.S.;Oslob,J.D.;Purkey,H.E.;Romanowski,M.J.;Silverman,J.A.;Tangonan,B.T.;Taverna,P.;Yang,W.;Yoburn,J.C.;Yu,C.H.;Zimmerman,K.M.;O'Brien,T.;Lew,W.Biol.Med.Chem.Lett.2009,19,5158. (b) Moriya,M.;Kishino,H.;Sakuraba,S.;Sakamoto,T.;Suga,T.;Takahashi,H.;Suzuki,T.;Ito,M.;Ito,J.;Moriya,R.;Takenaga,N.;Iwaasa,H.;Ishihara,A.;Kanatani,A.;Fukami,T.Biol.Med.Chem.Lett.2009,19,3568. (c) Lo,H.Y.;Bentzien,J.;Fleck,R.W.;Pullen,S.S.Biol.Med.Chem.Lett.2008,18,6218. (d) Xuan,G.;Han,J.;Li X.Eur.J.Med.Chem.2006,41,1080. (e) Pérez-Villanueva,J.;Hernández-Campos,A.;Yépez-Mulia,L.Biol.Med.Chem.2013,21,4221. (f) Chen,J.;Gao,L.-X.;Gong,J.-X.;Jiang,C.-S.;Yao,L.-G.;Li,J.-Y.;Li,J.;Xiao,W.;Guo,Y.-W.Biol.Med.Chem.2015,23,2211.
[16] (a) Ueda,S.;Buchwald,S.L.Angew.Chem.,Int.Ed.2012,51,10364. (b) Alma?i,D.;Alonso,D.A.;Gómez-Bengoa,E.;Nájera,C.J.Org.Chem.2009,74,6163. (c) Zhang,L.;Lee,M.-M.;Lee,S.-M.;Lee J.;Cheng,M.;Jeong,B.-S.;Park,H.-G.;Jew,S.-S.Adv.Synth.Catal.2009,351,3063. (d) Gómez-Torres,E.;Alonso,D.A.;Gómez-Bengoa,E.;Nájera,C.Org.Lett.2011,13,6106.
[17] (a) Rastogi,R.;Sharma,S.Synthesis 1983,861. (b) Cee,V.J.;Downing,N.S.Tetrahedron Lett.2006,47,3747. (c) Xie,Y.;Zhang,F.;Li,J.;Shi,X.Synlett 2010,901. (d) Deasy,R.E.;Slattery,C.N.;Maguire,A.R.;Kjell,D.P.;Hawk,M.K.N.;Joo,J.M.;Gu,R.L.;Moynihan,H.J.Org.Chem.2014,45,3688. (e) Artman,G.D.Ⅲ;Solovay,C.F.;Adams,C.M.;Diaz,B.;Dimitroff,M.;Ehara,T.;Gu,D.;Ma,F.;Liu,D.;Miller,B.R.;Pick,T.E.;Poon,D.J.;Ryckman,D.;Siesel,D.A.;Stillwell,B.S.;Swiftney,T.;Dyck,J.P.;Zhang,C.;Ji,N.Tetrahedron Lett.2010,51,5319. (f) Pollock,J.A.;Kim,S.H.;Katzenellenbogen,J.A.Tetrahedron Lett.2015,56,6097.
[18] Evindar,G.;Batey,R.A.Org.Lett.2003,5,133.
[19] Chi,Y.;Zhang,W.-X.;Xi,Z.Org.Lett.2014,16,6274.
[20] Ueda,S.;Buchwald,S.L.Angew.Chem.,Int.Ed.2012,51,10364.
[21] Kim,M.;Mulcahy,J.V.;Espino,C.G.;Bois,J.D.Org.Lett.2006,8,1073.
[22] Muñiz,K.;Martínez,C.J.Org.Chem.2013,78,2168.
[23] (a) Schultz,D.M.;Wolfe,J.P.Synthesis (Stuttg)2012,44,351. (b) Wolfe,J.P.Synlett 2008,2913. (c) Wolfe,J.P.Synlett 2006,571.
[24] Gainer,M.J.;Bennett,N.R.;Takahashi,Y.;Looper,R.E.Angew.Chem.,Int.Ed.2011,50,684.
[25] Hövelmann,C.H.;Streuff,J.;Brelot,L.;Muñiz,K.Chem.Commun.2008,28,2334.
[26] Zavesky,B.P.;Babij,N.R.;Fritz,J.A.;Wolfe,J.P.Org.Lett.2013,15,5420.
[27] Zavesky,B.P.;Babij,N.R.;Wolfe,J.P.Org.Lett.2014,16,4952.
[28] Li,J.;Neuville,L.Org.Lett.2013,15,6124.
[29] Li,J.;Wang,H.;Hou,Y.;Yu,W.;Xu,S.;Zhang,Y.Eur.J.Org.Chem.2016,2388.
[30] Wang,F.;Cai,S.;Liao,Q.;Xi,C.J.Org.Chem.2011,76,3174.
[31] Yu,H.;Liu,Q.;Li,Y.;Ni,C.Tetrahedron Lett.2012,53,5253.
[32] He,H.-F.;Wang,Z.-J.;Bao,W.Adv.Synth.Catal.2010,352,2905.
[33] Tran,L.Q.;Li,J.;Neuville,L.J.Org.Chem.2015,80,6102.
[34] Wang,Q.;Schreiber,S.L.Org.Lett.2009,11,5178.
[35] (a) Cohen,F.;Overman,L.E.J.Am.Chem.Soc.2001,123,10782. (b) Arnold,M.A.;Day,K.A.;Duron,S.G.;Gin,D.Y.J.Am.Chem.Soc.2006,128,13255. (c) Evans,P.A.;Qin,J.;Robinson,J.E.;Bazin,B.Angew.Chem.,Int.Ed.2007,46,7417. (d) Ishiwata,T.;Hino,T.;Koshino,H.;Hashimoto,Y.;Nakata,T.;Nagasawa,K.Org.Lett.2002,4,2921. (e) Rodriguez,R.A.;Steed,D.B.;Kawamata,Y.;Su,S.;Smith,T.C.;Steed,P.A.;Romesberg,F.E.;Baran,P.S.J.Am.Chem.Soc.2014,136,15403. (f) Ma,Z.;Wang,X.;Ma,Y.;Chen,C.Angew.Chem.,Int.Ed.2016,55,4763.
[36] Babij,N.R.;Wolfe,J.P.Angew.Chem.,Int.Ed.2012,51,4128.
[37] Babij,N.R.;Wolfe,J.P.Angew.Chem.,Int.Ed.2013,52,9247.
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