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机械化学条件下乙酰乙酸乙酯与查尔酮的Michael加成反应 被引量:3

Michael addition reactions of ethyl acetoacetate with chalcones under mechanochemical conditions
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摘要 研究了机械化学条件下乙酰乙酸乙酯与查尔酮及氮杂查尔酮的Michael加成反应。用该方法进行的反应不需要任何有机溶剂,仅10%当量的K2CO3就能使反应有效进行。在绝大多数情况下,通常的副反应被成功避免,因而产率较高,相应的Michael加成产物几乎能定量得到。对于加成产物中含有的一对非对映异构体(anti和syn)通过1H-NMR进行了归属指认。另外考察了其他催化剂对反应的影响。 Michael addition reactions of ethyl acetoacetate with chalcones and azachaleones were investigated under mechanochemical conditions. This protocol didn't require the use of any organic solvent during the reaction process and only 10% molar equivalent of K2 CO3 was enough to promote the reaction efficiently. In most cases, conventional side reactions were avoided and thus excellent yields were achieved;that was, almost all the Michael adducts could be obtained quantitatively. The desired Michael adducts consisting of two diastereoisomers anti and syn were determined and assigned by 1 H NMR analysis. And the influence of other catalysts on this Michael reaction was studied.
出处 《化学研究与应用》 CAS CSCD 北大核心 2013年第5期742-747,共6页 Chemical Research and Application
基金 国家自然科学基金项目(20902002 21242013)资助
关键词 机械化学 迈克尔加成 查尔酮 乙酰乙酸乙酯 绿色有机合成 mechanochemistry Michael addition chalcones ethyl acetoacetate green organic synthesis
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参考文献12

  • 1Bergman ED, Ginsberg D, Pappo R. The Michael reaction in organic reactions[MJ. New York:John Wiley&Sons Inc, 1959 :595-623.
  • 2Ganesh S, Sarkar A. Highly diastereoselective Michael ad?dition to 2-arylidene-I-tetralones complexed with Cr (CO)3[J]. Tetrahedron Lett ,1991 ,32(8):1085-1088.
  • 3Loupy A. Solvent-free reactions[J] . Top Curr Chern, 1999 , 206:153-207.
  • 4Tanaka K, Toda F. Solvent-free organic synthesis[J]. Chern Rev ,2000 ,100(3) :1025-1074.
  • 5Baig R B N , Varma R S. Alternative energy input: mecha?nochemical, microwave and ultrasound-assisted organic synthesis[J]. Chern Soc Rev ,2012 ,41 (4) :1559-1584.
  • 6Rodriguez B, Bruckmann A, Rantanen T ,et al. Solvent-free carbon-carbon bond formations in ball mills[J]. Adv Synth Catal,2oo7 ,349(14):2213-2233.
  • 7Zhang Z, Peng Z W, Hao M F, et al. Mechanochemical Diels-Alder cycloaddition reactions for straightforward syn- thesis of endo-norbornene derivatives[J]. Synlell,2010 (19):2895-2898.
  • 8Wang G W, GaoJ. Selective formation of spiro dihydro?furans and cyclopropanes through unexpected reaction of aldehydes with 1, 3-dicarbonyl compounds[J]. Org Lett, 2009,11 (11) :2 385-2 388.
  • 9Zhang Z, Dong Y W, Wang G W. Efficient and clean aldol condensation catalyzed by sodium carbonate in water[J] . Chern Lett,2oo3,32(1O) :966-967.
  • 10YamawakiJ ,Ando T ,Hanafusa T. N-Alkylation of amides and N-heterocycles with potassium fluoride on alumina[J]. Chern Lett, 1981,8: 1 143-1 146.

同被引文献23

  • 1韩荣弼,陈甡,吴学.2-硝基查尔酮类衍生物的合成[J].化学试剂,2006,28(4):243-244. 被引量:5
  • 2郭文龙,崔建兰,张漪,李育珍.Michael加成反应的研究进展[J].天津化工,2007,21(2):6-9. 被引量:5
  • 3Xie J W, Yue L, Chen W, et al. Highly enantioselective Michael addition of cyclic 1,3-dicarbonyl compounds to a ,/3-unsaturated ketones [ J ]. Org Lett,2007 ,9 :413-415.
  • 4Firouzabadi H, Iranpoor N. Silica gel catalyzed highly se- lective CS bond formation via Michael addition of thiols to a,/3-unsaturated ketones under solvent-free conditions [J]. J Mol Catal A : Chem,2006 ,249 :98-102.
  • 5Gao S, Tzeng T. Iodine catalyzed conjugate addition of mercaptans to ct,/3-unsaturated carboxylic acids under sol- vent-free condition [ J ]. Tetrahedron Lett. ,2006,47 : 1 889- 1 893.
  • 6Ahmed N, Lier J E V. Alumina supported-CeC13 "7H20- NaI:an efficient catalyst for the cyclization of 2'-aminoch- alcones to the corresponding 2-aryl-2,3-dihydroquinolin-4 (1H)-ones under solvent free conditions [ J]. Tetrahedron Lett,2007,48 : 13-15.
  • 7Bartoli G,Antonio G D, Giuli S, et al. The CeC13 .7H20/ NaI/SiO2 system as an efficient promoter for the Friedel- Crafts reaction of indoles to nitroalkenes under solvent-free conditions[ J]. Synthesis ,2008,2:320-324.
  • 8Yadav L D S, Kapoor R. An efficient protocol for multi- component stereoselective synthesis of 3-amino-2 (1H) - pyridinones using CeC13 -7HzO/NaI as a reaction promoter[ J]. Syrdett. ,2008,15:2 348-2 354.
  • 9Bartoli G, Giovannini R, Giuliani A et al. Solvent-free carbon-oxygen bond formation catalysed by CeC13~ 7H20/NaI : tetrahydropyranylation of gydroxy groups [ J ]. Eur J Org Chem,2006,1 476-1 482.
  • 10Silveira C C, Martins G M, Mendes S R. Regio-and stere- oselective synthesis of(Z)-2-arylsulfanyl allylic alcohols using anhydrous CeC13 as catalyst under solvent free con- ditions[ J]. Tetrahedron Lett ,2013,54:5 492-5 495.

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