期刊信息

  • 刊名: 河北师范大学学报(自然科学版)Journal of Hebei Normal University (Natural Science)
  • 主办: 河北师范大学
  • ISSN: 1000-5854
  • CN: 13-1061/N
  • 中国科技核心期刊
  • 中国期刊方阵入选期刊
  • 中国高校优秀科技期刊
  • 华北优秀期刊
  • 河北省优秀科技期刊

醋酸铵促进烯胺酮的双 Michael 加成反应研究

  • (1.滁州城市职业学院 医学院,安徽 滁州 239000; 2.安徽师范大学 化学与材料科学学院,安徽 芜湖 241002)
  • DOI: 10.13763/j.cnki.jhebnu.nse.202403002

NH4OAc-promoted Double Michael Addition Reactions of Enaminones

摘要/Abstract

摘要:

在醋酸铵作用下实现取代的 1,3-环己二酮对取代的N,N-二甲基烯胺酮的连续Michael加成反应,发展了一种合成结构新颖的3,3-二环己烯基-1-苯基丙酮类化合物的新方法.该反应在1,2-二氯乙烷中回流搅拌 40 min 即可得到目标产物,且具有较高的收率和优异的官能团兼容性.该方法具有原料廉价易得、实验操作简单的特点,为结构多样的烷基芳基酮类化合物的合成提供了一种新颖、实用的策略.

Abstract:

A new method for the synthesis of 3,3-dicyclohexenyl-1-phenylacetone compounds with novel structures was developed through the NH4OAc-promoted sequential Michael addition reactions of substituted 1,3-cyclohexanedione with substituted N,N-dimethylenaminone.This reaction proceeded in 1,2-dichloroethane under reflux and stir for 40 min,affording the desired compounds with good yields and functional group tolerance.This method has the characteristics of cheap and easily available raw materials,and simple experimental operations,providing a novel and practical strategy for the synthesis of structurally diverse alkylphenone derivatives.

参考文献 23

  • [1] BATES R W,KOÁW,BART V.The endo-aza-Michael Addition in the Synthesis of Piperidines and Pyrrolidines [J ].Organic & Biomolecular Chemistry,2020,18(5):810-829.doi:10.1039/c9ob02388g
  • [2] MIYANAGA A.Michael Additions in Polyketide Biosynthesis [J ].Natural Product Reports,2019,36(3):531-547.doi:10.1039/c8np00071a
  • [3] KRISHNA P R,SREESHAILAM A,SRINIVAS R.Recent Advances and Applications in Asymmetric aza-Michael Addition Chemistry [J ].Tetrahedron,2009,65(47):9657-9672.doi:10.1016/j.tet.2009.08.021
  • [4] JUSSEAU X,CHABAUD L,GUILLOU C.Synthesis of γ-butenolides and α,β-unsaturated γ-butyrolactams by Addition of Vinylogous Nucleophiles to Michael Acceptors [J ].Tetrahedron,2014,70(16):2595-2615.doi:10.1016/j.tet.2014.01.057
  • [5] VINOGRADOV M G,TUROVA O V,ZLOTIN S G.Recent Advances in the Asymmetric Synthesis of Pharmacology-relevant Nitrogen Heterocycles via Stereoselective aza-Michael Reactions [J ].Organic & Biomolecular Chemistry,2019,17(15):3670-3708.doi:10.1039/c8ob03034k
  • [6] ZHANG Y,WANG W.Recent Advances in Organocatalytic Asymmetric Michael Reactions [J ].Catalysis Science & Technology,2012,2(1):42-53.doi:10.1039/c1cy00334h
  • [7] YIN B Y,CROUTX-BARGHORN C,DELAITE C,et al.A New Synthetic Pathway Based on One-pot Sequential aza-Michael Addition and PhotoCuAAC Click Reactions [J ].RSC Advances,2019,9(9):4824-4831.doi:10.1039/c8ra10011j
  • [8] RAMELLA V,ROOSEN P C,VANDERWAL C D.Concise Formal Synthesis of the Pseudopterosins via Anionic Oxy-cope/transannular Michael Addition Cascade [J ].Organic Letters,2020,22(8):2883-2886.doi:10.1021/acs.orglett.0c00486
  • [9] REDDY R R,PANDA S,GHORAI P.Enantioselective Synthesis of Cyclohexadienone Containing Spiroketals via DyKat Ketalization/oxa-Michael Addition Cascade [J ].Journal of Organic Chemistry,2019,84(9):5357-5368.doi:10.1021/acs.joc.9b00371
  • [10] NAYAK S,PANDA P,BHAKTA S,et al.Current Advances of Organocatalytic Michael-Michael Cascade Reaction in the Synthesis of Highly Functionalized Cyclic Molecules [J ].RSC Advances,2016,6(98):96154-96175.doi:10.1039/c6ra21191g
  • [11] KAEWMEE B,RUKACHAISIRIKUL V,KAEOBAMRUNG J.Synthesis of Quinolines via Copper-catalyzed Domino Reactions of Enaminones [J ].Organic & Biomolecular Chemistry,2017,15(35):7387-7395.doi:10.1039/c7ob01867c
  • [12] ARSHADI S,VESSALLY E,EDJLALI L,et al.N-propargylic β-enaminocarbonyls:Powerful and Versatile Building Blocks in Organic Synthesis [J ].RSC Advances,2017,7(22):13198-13211.doi:10.1039/c7ra00746a
  • [13] ELASSAR A-Z A,EL-KHAIR A A.Recent Developments in the Chemistry of Enaminones [J ].Tetrahedron,2003,59(43):8463-8480.doi:10.1016/S0040-4020(03)01201-8
  • [14] AMAYE I J,HAYWOOD R D,MANDZO E M,et al.Enaminones as Building Blocks in Drug Development:Recent Advances in Their Chemistry,Synthesis,and Biological Properties [J ].Tetrahedron,2021,83:131984.doi:10.1016/j.tet.2021.131984
  • [15] XIA X F,NIU Y N.Recent Developments in the Synthesis of Nitrogen-containing Heterocycles from β-aminovinyl Esters/ketones as C—C—N Donors [J ].Organic & Biomolecular Chemistry,2022,20(2):282-295.doi:10.1039/d1ob01998h
  • [16] OBYDENNOV D L,EL-TANTAWY A I,SOSNOVSKIKH V Y.Synthesis of Multifunctionalized 2,3-dihydro-4-pyridones and 4-pyridones via the Reaction of Carbamoylated Enaminones with Aldehydes [J ].Journal of Organic Chemistry,2018,83(22):13776-13786.doi:10.1021/acs.joc.8b02075
  • [17] FANG G C,LIU J Q,FU J K,et al.Silver-catalyzed Cascade Reaction of β-enaminones and Isocyanoacetates to Construct Functionalized Pyrroles [J ].Organic Letters,2017,19(6):1346-1349.doi:10.1021/acs.orglett.7b00201
  • [18] CHEN X Y,ZHANG X T,WAN J P.Recent Advances in Transition Metal-free Annulation Toward Heterocycle Diversity Based on the C—N Bond Cleavage of Enaminone Platform [J ].Organic & Biomolecular Chemistry,2022,20(12):2356-2369.doi:10.1039/d2ob00126h
  • [19] GABER H M,BAGLEY M C,MUHAMMAD Z A,et al.Recent Developments in Chemical Reactivity of N,N-dimethylenamino Ketones as Synthons for Various Heterocycles [J ].RSC Advances,2017,7(24):14562-14610.doi:10.1039/c7ra00683g
  • [20] ZHANG C Y,WANG W,ZHU X C,et al.Synthesis of Indolizines via Tf2O-mediated Cascade Reaction of Pyridyl-enaminones with Thiophenols/thioalcohols [J ].Organic Letters,2023,25(7):1192-1197.doi:10.1021/acs.orglett.3c00177
  • [21] LU F L,ZHANG K,YAO Y X,et al.Electrochemical Oxidative Thiocyanation and Amination of Enaminones Towards the Synthesis of Multi-substituted Alkenes [J ].Green Chemistry,2021,23(2):763-766.doi:10.1039/d0gc03590d
  • [22] LUO T,WU H Z,LIAO L H,et al.Synthesis of 3,3-dihalogenated 2-aminochromanones via Tandem Dihalogenation and Cyclization of o-hydroxyarylenaminones with NXS(X=Cl or Br) [J ].Journal of Organic Chemistry,2021,86(21):15785-15791.doi:10.1021/acs.joc.1c01851
  • [23] LIU T,WEI L,ZHAO B L,et al.Copper-catalyzed Enaminone C(sp2)-N Bond Phosphonation for Stereoselective Synthesis of Alkenylphosphonates [J ].Journal of Organic Chemistry,2021,86(14):9861-9868.doi:10.1021/acs.joc.1c00862