碘催化色酮与吡啶乙酸乙酯[3+2]环化合成结构新颖的中氮茚类化合物
Iodine-catalyzed [3+2] cyclization for the synthesis of structurally novel indolizines with chromones and 2-pyridylacetates
作者：董凯凯;黄强;易东;姬建新;付强;
Author：
收稿日期： 年卷（期）页码：2020,35(01):-16-23
期刊名称：华西药学杂志
Journal Name：WEST CHINA JOURNAL OF PHARMACEUTICAL SCIENCES
关键字：中氮茚;环加成;色酮;吡啶乙酸乙酯;单质碘;合成;结构新颖;自由基反应
Key words：
基金项目：
中文摘要
目的建立简单、绿色、高效合成结构新颖的中氮茚类化合物的方法。方法以色酮和吡啶乙酸乙酯为底物、1,4-二氯苯为溶剂、二叔丁基过氧化物为氧化剂,在单质碘的催化下,制备中氮茚类化合物。结果与讨论发展了一种操作简单、绿色的方法,合成了一系列结构新颖的中氮茚类化合物,产物结构经~1HNMR、~(13)CNMR、~(19)FNMR和HR-MS表征。该反应具有底物适用范围广、收率高和条件温和的优点。初步的机理研究表明反应产生了自由基中间体。
参考文献
[1] Smith SC,Clarke ED,Ridley SM,et al.Herbicidal indolizine-5,8-diones:Photosystem I redox mediators[J].Pest Manag Sci,2005,61(1):16-24.
[2] De Bolle L,Andrei G,Snoeck R,et al.Potent,selective and cell-mediated inhibition of human herpesvirus 6 at an early stage of viral replication by the non-nucleoside compound CMV423[J].Biochem Pharmacol,2004,67(2):325-336.
[3] Hagishita S,Yamada M,Shirahase K,et al.Potent inhibitors of secretory phospholipase A2:Synthesis and inhibitory activities of indolizine and indene derivatives[J].J Med Chem,1996,39(19):3636-3658.
[4] Chernyak D,Gadamsetty SB,Gevorgyan V.Low temperature organocopper-mediated two-component cross coupling/cycloisomerization approach toward N-fused heterocycles[J].Org Lett,2008,10(11):2307-2310.
[5] Kim M,Jung Y,Kim I.Domino knoevenagel condensation/intramolecular aldol cyclization route to diverse indolizines with densely functionalized pyridine units[J].J Org Chem,2013,78(20):10395-10404.
[6] Shi F,Zhang Y,Lu Z,et al.Transition-metal-free synthesis of indolizines from electron-deficient alkenes via one-pot reaction using TEMPO as an oxidant[J].Synthesis,2016,48(3):413-420.
[7] Li H,Li X,Yu Y,et al.Synthesis of indolizines via reaction of 2-substitued azaarenes with enals by an amine-NHC relay catalysis[J].Org Lett,2017,19(8):2010-2013.
[8] Reddy NNK,Mohan DC,Adimurthy S.Metal-free synthesis of indolizines through oxidative C-C and C-N bond formations of C(sp3)-H bonds[J].Tetrahedron Lett,2016,57(10):1074-1078.
[9] Chen Z,Liang P,Ma X,et al.Catalyst-free annulation of 2-pyridylacetates and ynals with molecular oxygen:An access to 3-acylated indolizines[J].J Org Chem,2019,84(3):1630-1639.
[10] Hu DY,Li MS,Zhong WW,et al.Direct synthesis of α-hydroxyketone phosphates from terminal alkynes and H-phosphine oxides in the presence of PhI(OAc)2 and H2O [J].Chin Chem Lett,2016,27(11):1691-1695.
[11] Li MS,Zhang Q,Hu DY,et al.Catalyst-free direct difunctionalization of alkenes with H-phosphine oxides and dioxygen:A facile and green approach to β-hydroxyphosphine oxides[J].Tetrahedron Lett,2016,57(24):2642-2646.
[12] 何华玲,张强,姬建新,等.CuBr2/Ag2CO3催化苄胺氧化酰胺化合成N-苄基苯甲酰胺[J].华西药学杂志,2017,32(3):223-227.
[13] 杨路,陈粟源,易东,等.Dess-Martin试剂促进吲哚硫醚合成反应的研究[J].华西药学杂志,2018,33(1):8-12.
[14] 高明,王华斌,黄强,等.铜铁共催化2-芳基丙烯酸酯的脱酯氧膦化反应[J].华西药学杂志,2019,34(1):15-21.
[15] Reddy NNK,Donthiri RR,Ravi C,et al.Iodine-catalyzed[3+2]cyclization of 2-pyridylesters and chalcones:Metal-free approach for the synthesis of substituted indolizines[J].Tetrahedron Lett,2016,57(16):3243-3246.
【关闭】
