English
往期目录
新闻公告
More
化学进展 2009, Vol. 21 Issue (05): 997-1007 前一篇   后一篇

• 综述与评论 •

丙二腈在多组分反应中的应用*

王琦芳; 宋肖锴; 颜朝国**   

  1. (扬州大学化学化工学院 扬州 225002)
  • 收稿日期:2008-05-28 修回日期:2008-07-04 出版日期:2009-05-24 发布日期:2009-05-05
  • 通讯作者: 颜朝国 E-mail:cgyan@yzu.edu.cn
  • 基金资助:

    国家自然科学基金

下载PDF ( 4473 ) 引用
导出

Application of Malononitrile in Multicomponent Reactions

Wang Qifang ;  Song Xiaokai ;  Yan Chaoguo**   

  1.  (College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002, China)
  • Received:2008-05-28 Revised:2008-07-04 Online:2009-05-24 Published:2009-05-05
  • Contact: Yan Chaoguo E-mail:cgyan@yzu.edu.cn

丙二腈分子中的氰基作为强吸电子基团活化亚甲基，也是良好的离去基团，以及氰基的碳氮三键可进行加成反应，使得丙二腈是一种非常特别的化合物。它具有非常丰富的反应性质，可以发生Knoevenagel缩合、Michael加成、环化和消去等反应，是进行多组分合成反应的优良试剂。由其参加的多组分合成反应已经成为合成众多碳环和杂环化合物的重要方法。本文综述了丙二腈在多组分反应中的研究进展，介绍了近年来丙二腈参加的多组分反应合成环状化合物的成功事例，展望了丙二腈反应的发展方向。

关键词： 多组分反应, 丙二腈, 缩合反应, Michael加成, 环化反应, 消去反应

Malononitrile is a particularly versatile compound, since the strongly electron-withdrawing cyano groups activate the methylene group, the polar multiple bond is suitable for nucleophilic addition and is also a good leaving group for substitution. The methylene group and one or both cyano groups can take part in condensation reactions to give a variety of addition products and heterocyclic compounds. This unique reactivity makes malononitrile an important candidate for multicomponent reactions. There have been a lot of multicomponent reactions with malononitrile for preparing carbocyclic and heterocyclic compounds. We reviews potential applications of malononitrile in multicomponent reactions, especially the recent representative examples for preparing heterocyclic compounds. The perspective for future development in this field is also briefly discussed.

Contents
1 Knoevenagel condensations
1.1 Reactions of aldehyde with malononitrile
1.2 Reactions of ketones with malononitrile
1.3 Synthesis of cyclopropanes
2 Michael additions
3 Elimination reactions

Key words: multicomponent reactions, malononitrile, Knoevenagel condensation, Michael addition, cyclization, elimination

中图分类号: 

()

[ 1 ] 　Freeman F. Chem. Rev. , 1969 , 69 : 591 —624
[ 2 ] 　Bigi F , Conforti M L , Maggi R , Piccinno A , Sartori G. Green Chem. , 2000 , 2 : 101 —103
[ 3 ] 　Wang X S , Zeng Z S , Li YL , et al . Synth. Commun. , 2005 , 35 :1915 —1920
[ 4 ] 　王官武(Wang G W) , 王宝亮(Wang B L) . 有机化学(Chin.J . Org. Chem. ) , 2004 , 24 (1) : 85 —87
[ 5 ] 　Kambe S , Sarro K. Synth. Commun. , 1980 , 366 —368
[ 6 ] 　Ren ZJ , Cao W G, Tong WQ. Synth. Commun. , 2002 , 32 (22) :3475 —3479
[ 7 ] 　高原(Gao Y) , 史达清(Shi D Q) , 周龙虎(Zhou L H) . 有机化学(Chin. J . Org. Chem. ) , 1996 , 13 (6) : 548 —551
[ 8 ] 　屠树江(Tu S J ) , 荣良策(Rong L C) , 高原(Gao Y) , 郭苏闵(Guo S M) , 鲁水华(Lu S H) , 杨晓洁(Yang XJ ) . 有机化学(Chin. J . Org. Chem. ) , 2002 , 22 (5) : 364 —366
[ 9 ] 　王香善(Wang X S) , 曾兆森(Zeng Z S) , 史达清(Shi D Q) ,魏贤勇(Wei X Y) , 宗志敏(Zong Z M) . 有机化学(Chin. J .Org. Chem. ) , 2005 , 25 (9) : 1138 —1141
[10 ] 　王香善(Wang X S) , 曾兆森(Zeng Z S) , 李玉玲(Li YL) , 史达清(Shi D Q) , 魏贤勇(Wei X Y) , 宗志敏(Zong ZM) . 有机化学(Chin. J . Org. Chem. ) , 2005 , 25 (9) : 1107 —1109
[11 ] 　史达清(Shi D Q) , 张姝(Zhang Z) , 庄启亚(Zhuang Q Y) , 屠树江(Tu S J ) , 胡宏纹(Hu H W) . 有机化学(Chin. J . Org.Chem. ) , 2003 , 23 (11) : 1314 —1316
[12 ] 　Hassanien MA , Zahran S A , EI2Glaby S A. J . Indian Chem. Soc. ,1999 , 76 : 350 —354
[13 ] 　Guo S B , Wang S X, Li J T. Syn. Commun. , 2007 , 37 (13) :2111 —2120
[14 ] 　Wang X S , Shi D Q , Tu S J . Chin. J . Chem. , 2003 , 21 : 1114 —1117
[15 ] 　王香善(Wang X S) , 史达清(Shi D Q) , 魏贤勇(Wei X Y) ,宗志敏(Zong ZM) . 有机化学(Chin. J . Org. Chem. ) , 2004 ,24 (11) : 1454 —1457
[16 ] 　Tu S J , Gao Y, Guo C , Shi D Q , Lu Z S. Synth. Commun. , 2002 ,32 (14) : 2137 —2141
[17 ] 　屠树江(Tu SJ ) , 蒋虹(Jiang H) , 庄启亚(Zhuang Q Y) , 缪春宝(Miao C B) , 史达清(Shi D Q) , 王香善(Wang X S) , 高原(Gao Y) . 有机化学(Chin. J . Org. Chem. ) , 2003 , 23 (5) :488 —490
[18 ] 　Saeed B , Morteza B , Masoumeh S A , Shohreh H , Peyman S. Syn.Commun. , 2007 , 37 (7) : 1097 —1108
[19 ] 　Elinson M N , Dorofeev A S , Feducovich S K, Gorbunov S V ,Nasybullin R F , Miloserdov F M, Nikishin G I. Eur. J . Org.Chem. , 2006 , 4335 —4339
[20 ] 　Elinson M N , Vereshchagin A N , Feducovich S K, Zaimovskaya T A , Starikova Z A , Belyakov P A , Nikishin G I. Tetrahedron Lett . ,2007 , 48 (38) : 6614 —6619
[21 ] 　Heber D , Stoyanov E V. Synthesis , 2003 , 2 : 227 —232
[22 ] 　Saikia A. Synlett , 2004 , 12 : 2247 —2248
[23 ] 　Fotouhi L , Heravi MM, Fatehi A , Bakhtiari K. Tetrahedron Lett . ,2007 , 48 (31) : 5379 —5381
[24 ] 　靳通收(Jin T S) , 王爱卿(Wang A Q) , 张建设(Zhang J S) ,张伏生(Zhang F S) , 李同双(Li T S) . 有机化学(Chin. J .Org. Chem. ) , 2004 , 24 (12) : 1598 —1600
[25 ] 　Jin T S , Wang A Q , Wang X, Zhang J S , Li T S. Synlett , 2004 , 5 :871 —873
[26 ] 　Balalaie S , Bararjanian M, Amani A M, Movassagh B. Synlett ,2006 , 2 : 263 —266
[27 ] 　Ballini R , Bosica G, Conforti ML , Maggi R , Mazzacani A , Righi P , Sartori G. Tetrahedron , 2001 , 57 : 1395 —1398
[28 ] 　Jin T S , Xiao J C , Wang S J , Li T S , Song X R. Synlett , 2003 ,13 : 2001 —2004
[29 ] 　Kidwai M, Saxena S , Khan M K R , Thukral S S. Bioorg. Med.Chem. Lett . , 2005 , 15 : 4295 —4298
[30 ] 　Kumar D , Reddy V B , Mishra B G, Rana R K, Nadagoudac M N ,Varmac R S. Tetrahedron , 2007 , 63 : 3093 —3097
[31 ] 　Shanthi G, Perumal P T. Tetrahedron Lett . , 2007 , 48 (38) : 6785 —6789
[32 ] 　王香善(Wang X S) , 史达清(Shi D Q) , 屠树江(Tu S J ) . 有机化学(Chin. J . Org. Chem. ) , 2003 , 23 (2) : 203 —206
[33 ] 　Kumar D , Reddy V B , Mishra B G, Rana R K, Nadagouda M N ,Varma R S. Tetrahedron , 2007 , 63 (15) : 3093 —3097
[34 ] 　Fringuelli F , Piermatti O , Pizzo F. Synthesis , 2003 , 15 : 2331 —2334
[35 ] 　Costa M, Areias F , Proenaca F , et al . J . Org. Chem. , 2008 , 73(5) : 1954 —1962
[36 ] 　Rodinovskaya L , Shestopalov A , Gromova A , Shestopalov A.Synthesis , 2006 , 14 : 2357 —2370
[37 ] 　Abdolmohammadi S , Balalaie S. Tetrahedron Lett . , 2007 , 48 :3299 —3303
[38 ] 　张雪利(Zhang XL) , 黄毅(Huang Y) , 李卓宁(Li ZN) , 吕玉娟(LüY J ) , 高原( Gao Y) . 有机化学( Chin. J . Org.Chem. ) , 2006 , 26 (10) : 1434 —1436
[39 ] 　王香善(Wang X S) , 曾兆森(Zeng Z S) , 史达清(Shi D Q) ,屠树江(Tu S J ) , 魏贤勇(Wei X Y) , 宗志敏(Zong ZM) . 有机化学(Chin. J . Org. Chem. ) 2004 , 24 (12) : 1595 —1597
[40 ] 　王香善(Wang X S) , 曾兆森(Zeng Z S) , 李玉玲(Li YL) , 史达清(Shi D Q) , 屠树江(Tu SJ ) , 魏贤勇(Wei X Y) , 宗志敏(Zong ZM) . 有机化学(Chin. J . Org. Chem. ) , 2006 , 26 (2) :228 —232
[41 ] 　史达清(Shi D Q) , 王静(Wang J ) , 庄启亚(Zhuang Q Y) , 王香善(Wang X S) . 有机化学(Chin. J . Org. Chem. ) , 2006 , 26(5) : 643 —647
[42 ] 　Ahmad S , Sima S , Abbas R. Syn. Commun. , 2007 , 37 ( 3 ) :491 —499
[43 ] 　Magedov I V , Manpadi M, Evdokimov N M, Elias E M, Rozhkova E , et al . Bioorg. Med. Chem. Lett . , 2007 , 17 : 3872 —3876
[44 ] 　Quiroga J , Alvarado M, Insuasty B , Moreno R , Ravina E , Esterez L , De Almerida R H T. J . Heterocycl . Chem. , 1999 , 36 : 1311 —1316
[45 ] 　Evdokimov N M, Magedov I V , Kireev A S , Kornienko A. Org.Lett . , 2006 , 8 (5) : 899 —902
[46 ] 　Evdokimov N M, Kireev A S , Yakovenko A A , Antipin M Y,Magedov I V , Kornienko A. J . Org. Chem. , 2007 , 72 : 3443 —3453
[47 ] 　Evdokimov N M, Kireev A S , Yakovenko A A , Antipin M Y,Magedov I V , Kornienko A. Tetrahedron Lett . , 2006 , 47 : 9309 —9312
[48 ] 　Tu S J , Jiang B , Jiang H , et al . Tetrahedron , 2007 , 63 : 5406 —5414
[49 ] 　Guo K, Mutter R , Heal W, et al . Eur. J . Med. Chem. , 2008 ,43 : 93 —106
[50 ] 　Guo K, Thompson M J , Reddy T R K, Mutter R , Chen B.Tetrahedron , 2007 , 63 : 5300 —5311
[51 ] 　Brindaban C , Ranu B C , Jana R , Sowmiah S. J . Org. Chem. ,2007 , 72 : 3152 —3154
[52 ] 　王香善(Wang X S) , 曾兆森(Zeng Z S) , 史达清(Shi D Q) ,屠树江(Tu S J ) , 魏贤勇(Wei X Y) , 宗志敏(Zong ZM) . 有机化学(Chin. J . Org. Chem. ) , 2006 , 26 (2) : 256 —259
[53 ] 　Tu S J , Cao L J , Zheng Y, Shao Q Q , Zhou D X, Li C M.Ultrasonics Sonochemistry , 2008 , 15 : 217 —221
[54 ] 　Fadel S , Hajbi Y, Rakib E M, Khouili M, Pujol M D , Guillaumet G. Synth. Commun. , 2004 , 12 : 2195 —2204
[55 ] 　朱松磊(Zhu S L) , 屠树江(Tu S J ) , 李团结(Li TJ ) , 章晓镜(Zhang X J ) , 纪顺俊(Ji S J ) , 张勇( Zhang Y) . 有机化学(Chin. J . Org. Chem. ) , 2005 , 25 (8) : 987 —990
[56 ] 　Tu S J , Li C M, Li G G, Cao L J , Shao Q Q , Zhou D X, Jiang B ,Zhou J F , Xia M. J . Comb. Chem. , 2007 , 9 : 1144 —1148
[57 ] 　Krishnaiah A , Narsaiah B. J . Fluorine Chem. , 2001 , 109 : 183 —187
[58 ] 　李玉玲(Li YL) , 杜百祥(Du B X) , 王香善(Wang X S) , 曾兆森(Zeng Z S) , 史达清(Shi D Q) , 屠树江(Tu SJ ) . 有机化学(Chin. J . Org. Chem. ) , 2006 , 26 (3) : 346 —348
[59 ] 　Wang X S , Zhang M M, Jiang H , Yao C S , Tu S J . Tetrahedron ,2007 , 63 : 4439 —4449
[60 ] 　Kumar S , Sharma P , Kapoor K K, Hundal MS. Tetrahedron , 2008 ,64 (3) : 536 —542
[61 ] 　Shintani T, Kadono H , Kikuchi T, Schubert T, Shogase Y,Shimazaki M. Tetrahedron Lett . , 2003 , 44 : 6567 —6569
[62 ] 　Marchalín S , BaumlováB , Baran P , Oulyadi H , Daīch A. J . Org.Chem. , 2006 , 71 : 9114 —9127
[63 ] 　Shi D Q , Tu S J , Yao S C , Wang X S , Wang Y C. Synth.Commun. , 2002 , 32 (20) : 3137 —3142
[64 ] 　史达清(Shi D Q) , 屠树江(Tu S J ) , 王香善(Wang X S) , 姚昌盛(Yao S C) , 于晨侠(Yu C X) , 王玉成(Wang YC) . 结构化学(Chin. J . Struct . Chem. ) , 2001 , 20 (6) : 501 —504
[65 ] 　Michaud D , Hamelin J , Texier-Boullet F , Toupet L. Tetrahedron ,2002 , 58 : 5865 —5875
[66 ] 　Lu X Y, Lu Z, Zhang X M. Tetrahedron , 2006 , 62 : 457 —460
[67 ] 　Tran Y S , Kwon O. J . Am. Chem. Soc. , 2007 , 129 : 12632 —12633
[68 ] 　Grigg R , Inman M, Kilner C , Kêppen I , Marchbank J , Selby P ,Sridharan V. Tetrahedron , 2007 , 63 (27) : 6152 —6169
[69 ] 　Nair V , Deepthi A , Beneesh P B , Eringathodi S. Synthesis , 2006 ,9 : 1443 —1446
[70 ] 　Zhou L , Hirao T. Tetrahedron Lett . , 2000 , 41 : 8517 —8521
[71 ] 　Kratschmer W, Lamb L D , Fostiropoulos K, Huffman D R. Nature ,1990 , 347 : 354 —358
[72 ] 　Li Y J , Wang G W, Li J X, Liu Y C. New J . Chem. , 2004 , 28(8) : 1043 —1047
[73 ] 　Wang X S , Zhang M M, Li Q , Yao C S , Tu S J . Tetrahedron ,2007 , 63 : 5265 —5273
[74 ] 　Kozik B , Wilamowski J , Córa M, Sepio¤ J J . Tetrahedron , 2008 ,64 : 6452 —6460
[75 ] 　Al-Omran F , El-Khair A A , Elnagdi M H. Organic Prep. Proced.Int . , 1998 , 30 (2) : 211 —241
[76 ] 　Yan C G, Song X K, Wang Q F , Sun J , Siemeling U , Bruhn C.Chem. Commun. , 2008 , 1440 —1442
[77 ] 　Wang G W, Cheng B. ARKIVOC , 2004 , (ix) : 4 —8
[78 ] 　DunhamJ C , Richardson A D , Sammelson R E. Synthesis , 2006 ,4 : 680 —686
[79 ] 　Xue D , Chen Y C , Cui X, et al . J . Org. Chem. , 2005 , 70 :3584 —3591
[80 ] 　Shestopalov AM, Emeliyanova YM, Shestopalov A A , Rodinovskaya L A , Niazimbetova Z I , Evans D H. Tetrahedron , 2003 , 59 :7491 —7496
[81 ] 　Asokan C V , Anabha E R , Thomas A D , Jose A M, Lethesh K C ,Prasanth M, Krishanraj K U. Tetrahedron Lett . , 2007 , 48 (32) :5641 —5643
[82 ] 　Elinson M N , Ilovaisky A I , Dorofeev A S , Merkulova V M,Stepanov N O , Miloserdov E M, Ogibin Y N , Nikishin G I.Tetrahedron , 2007 , 63 (42) : 10543 —10548
[83 ] 　Zhu S L , Ji S J , Zhang Y. Tetrahedron , 2007 , 63 (38) : 9365 —9372
[84 ] 　Shanthi G, Subbulakshmi G, Perumal P T. Tetrahedron , 2007 , 63(9) : 2057 —2063
[85 ] 　Redkin R G, Shemchuk L A , Chernykh V P , Shishkin O V ,Shishkina S V. Tetrahedron , 2007 , 63 (46) : 11444 —11450
[86 ] 　O’Callaghan C N , McMurry TB H. J . Chem. Research (S) , 1999 ,458 —459
[87 ] 　Amr A G E , Mohamed A M, Mohamed S F , Abdel-Hafez N A ,Hammam A E F G. Bioorg. Med. Chem. , 2006 , 14 : 5481 —5488
[88 ] 　Xue D , Chen Y C , Wang Q W, Cun L F , Zhu J , Deng J G. Org.Lett . , 2005 , 7 (23) : 5293 —5296
[89 ] 　Xue D , Li J , Zhang Z T, Deng J G. J . Org. Chem. , 2007 , 72(14) : 5443 —5445
[90 ] 　Milart P , Wilamowski J , Sepiot J J . Tetrahedron , 1998 , 54 (51) :15643 —15656
[91 ] 　Sepiot J , Milart P. Tetrahedron , 1985 , 41 (22) : 5261 —5265
[92 ] 　RongL C , Han H X, Yang F , Yao H , Jiang H , Tu S J . Syn.Commun. , 2007 , 37 (21) : 3767 —3772
[93 ] 　Cui S L , Lin X F , Wang Y G. J . Org. Chem. , 2005 , 70 : 2866 —2869
[94 ] 　Abdelrazek F M, El2Din A M S , Mekky A E. Tetrahedron , 2001 ,57 : 6787 —6791
[95 ] 　Castanedo GM, Sutherlin D P. Tetrahedron Lett . , 2001 , 42 (41) :7181 —7184
[96 ] 　Barnes D M, Haight A R , Hameury T, McLaughlin M A , Mei J Z,TedrowJ S , Toma J D R. Tetrahedron , 2006 , 62 (39) : 11311 —11319
[97 ] 　Gangjee A , Zeng Y B , Talreja T, McGuire J J , Kisliuk R L ,Queener S F. J . Med. Chem. , 2007 , 50 : 3046 —3053
[98 ] 　Al-Omran F , Elassar A A , El-Khair A A. Tetrahedron , 2001 , 57 :10163 —10170.
[99 ] 　Lebel H , Marcoux J F , Molinaro C , Charette A B. Chem. Rev. ,2003 , 103 : 977 —1050
[100 ] Kulinkovich O G, Meijere A. Chem. Rev. , 2000 , 100 : 2789 —2834
[101 ] Ye S , Huang Z Z, Xa C A , Tang Y, Dai L X. J . Am. Chem.Soc. , 2002 , 124 (11) : 2432 —2433
[102 ] McCooey S H , McCabe T, Connon S J . J . Org. Chem. , 2006 , 71(19) : 7494 —7497
[103 ] Elinson M N , Lizunova T L , Ugrak B I , et al . Tetrahedron Lett . ,1993 , 34 (36) : 5795 —5798
[104 ] Elinson M N , Feducovich S K, Lizunova T L , Nikishin G I.Tetrahedron , 2000 , 56 : 3063 —3069
[105 ] Elinson M N , Feducovich S K, Starikova Z A , et al . Tetrahedron ,2004 , 60 : 11743 —11749
[106 ] Elinson M N , Feducovich S K, Stepanov N O , et al . Tetrahedron ,2008 , 64 : 708 —713
[107 ] Elinson M N , Feducovich S K, Nikishin G I , et al . Tetrahedron Lett . , 2006 , 47 (51) : 9129 —9133
[108 ] Kojima S , Hiroike K, Ohkata K. Tetrahedron Lett . , 2004 , 45 (18) :3565 —3568
[109 ] Kojima S , Fujitomo K, Shinohara Y, Shimizu M, Ohkata K.Tetrahedron Lett . , 2000 , 41 (50) : 9847 —9851
[110 ] Vo N H , Eyermann C J , Hodge C N. Tetrahedron Lett . , 1997 , 38(46) : 7951 —7954
[111 ] Yamada S , Yamamoto J , Ohta E. Tetrahedron Lett . , 2007 , 48 (5) :855 —858
[112 ] Zhang T H , Lu P , Wang F , Wang GW. Biomol . Chem. , 2003 , 1 :4403 —4407
[113 ] Keshavarz K M, Knight B , Haddon R C , Wudl F. Tetrahedron ,1996 , 52 (14) : 5149 —5159
[114 ] Shestopalov A , Rodinovskaya L , Shestopalov A , Zlotin S , Nesterov V. Synlett . , 2003 , 15 : 2309 —2312
[115 ] Leitich J , Heise I. J . Photochem. Photobio. A:Chem. , 2006 , 146 :137 —140
[116 ] Victory P , Borrell J I , Vidal2Ferran A. Tetrahedron Lett . , 1991 , 32(39) : 5375 —5378
[117 ] 姚昌盛(Yao C S) , 高春梅(Gao C M) , 刘红宇(Liu H Y) , 于晨侠(Yu C X) , 屠树江( Tu S J ) . 徐州师范大学学报(J .Xuzhou Norm. Univ. ) , 2005 , 23 (1) : 51 —53
[118 ] Inokuma T, Hoashi Y, Takemoto Y. J . Am. Chem. Soc. , 2006 ,128 : 9413 —9419
[119 ] Mont N , TeixidóJ , Borrell J I , Kappe C O. Tetrahedron Lett . ,2003 , 44 : 5385 —5387
[120 ] Girgis A S , Mishriky N , Ellithey M, Hosni H M, Farag H. Bioorg.&Med. Chem. , 2007 , 15 : 2403 —2413
[121 ] Zhou WJ , Ji S J , Shen Z L. J . Organomet . Chem. , 2006 , 691 :1356 —1360
[122 ] Goda F E , Abdel-Aziz A A M, Attef O A. Bioorg. Med. Chem. ,2004 , 12 : 1845 —1852
[123 ] Yu Z, Velasco D. Tetrahedron Lett . , 1999 , 40 : 3229 —3232
[124 ] Tu S J , Jiang B , Zhang Y, Jia R H , Zhang , J Y, Yao C S , Shi F.Org. Biomol . Chem. , 2007 , 5 : 355 —359
[125 ] Victory P , Alvarez2Larena A , Germain G, Kessels R , Piniella J F ,Vidal2Ferran A. Tetrahedron , 1995 , 51 (1) : 235 —242
[126 ] 靳通收(Jin T S) , 尹影( Yin Y) , 刘利宾(Liu L B) , 赵莹(Zhao Y) , 李同双(Li T S) . 有机化学(Chin. J . Org. Chem. ) ,2007 , 27 (2) : 261 —265
[127 ] Li J T, Chen G F , Yang W Z, Li T S. Ultrasonics Sonochem. ,2003 , 10 : 123 —126
[128 ] Saxena A S , Goel A , Ram V J . Synlett , 2002 , 9 : 1491 —1492
[129 ] Agarwal N , Saxena A S , Farhanullah , Goel A , Ram V J .Tetrahedron , 2002 , 58 : 8793 —8798
[130 ] Pratap R , Ram V J . J . Org. Chem. , 2007 , 72 : 7402 —7405
[131 ] Klimova E I , García MM, Berestneva T K, Toledano C A , Toscano R A , Backinowsky L V. Eur. J . Org. Chem. , 2006 , 4755 —4760
[132 ] Saikia A , Chetia A , Bora U , Boruah R C. Synlett . , 2003 , 10 :1506 —1508
[133 ] Abdelrazek F M, El-Din A M S , Mekky A E. Tetrahedron , 2001 ,57 : 1813 —1817
[1] 闫保有, 李旭飞, 黄维秋, 王鑫雅, 张镇, 朱兵. 氨/醛基金属有机骨架材料合成及其在吸附分离中的应用[J]. 化学进展, 2022, 34(11): 2417-2431.
[2] 李路瑶, 徐鑫尧, 朱博, 常俊标. 吡唑酮化合物在催化不对称反应中的应用[J]. 化学进展, 2020, 32(11): 1710-1728.
[3] 杨宇东, 游劲松. 基于螯合导向C—H/C—H氧化交叉偶联/环化反应策略构筑稠杂芳烃化合物[J]. 化学进展, 2020, 32(11): 1824-1834.
[4] 戴立信*. Ullmann反应百年纪念及近期复兴——兼及碳-杂原子键的形成[J]. 化学进展, 2018, 30(9): 1257-1297.
[5] 丁奇峰, 杨雅琼, 缪文俊, 黄和, 于杨*, 黄菲*. 基于N,S-缩烯酮的杂环合成的研究[J]. 化学进展, 2018, 30(11): 1615-1623.
[6] 郑勇鹏, 许家喜. Thorpe-Ingold效应及其在有机成环反应中的应用[J]. 化学进展, 2014, 26(09): 1471-1491.
[7] 刘硕, 应安国, 倪宇翔, 杨建国, 许松林. 功能离子液体在Michael加成中的应用[J]. 化学进展, 2013, 25(08): 1313-1324.
[8] 张文生, 李伟, 匡春香. 1,1-二溴-2-取代苯基乙烯在环化反应中的应用[J]. 化学进展, 2013, 25(07): 1149-1157.
[9] 朱映光 翟昌伟 胡文浩. 不对称多组分反应[J]. 化学进展, 2010, 22(07): 1380-1396.
[10] 刘利 王东. “水上” (“on water”) 有机反应*[J]. 化学进展, 2010, 22(07): 1233-1241.
[11] 廉永福,袁福龙,郭丽华,刘美玲. 内嵌金属富勒烯的笼外化学修饰*[J]. 化学进展, 2008, 20(06): 909-917.
[12] 徐峻. 化学多样性空间探索与组合药物设计[J]. 化学进展, 1999, 11(03): 286-.
阅读次数
全文


摘要

丙二腈在多组分反应中的应用*