铑（III）催化N-磺酰基2-甲酰苯胺与烯烃环化制备（2H）喹啉

催化学报 , 2014, (11): 1840-1845. doi: 10.1016/S1872-2067(14)60160-1

铑（III）催化N-磺酰基2-甲酰苯胺与烯烃环化制备（2H）喹啉

张亦猛 ^1, , 张涛 ^2, , 詹豪强 ^3, , 李兴伟 ^4,

1.西华师范大学化学化工学院，四川省化学合成与污染控制重点实验室，四川南充637009; 中国科学院大连化学物理研究所，辽宁大连116023

2.中国科学院大连化学物理研究所，辽宁大连116023; 中南民族大学化学与材料学院，湖北武汉430074

3.西华师范大学化学化工学院，四川省化学合成与污染控制重点实验室，四川南充637009

4.中国科学院大连化学物理研究所,辽宁大连,116023

基金项目: the National Natural Science Foundation of China (21272231)

关键词：三价铑 , 氮-磺酰基2-氨基苯甲醛 , 烯烃 , 喹啉衍生物

Rh(III)-catalyzed synthesis of (dihydro)quinolines via the annulation of N-sulfonyl 2-aminobenzaldehydes with olefins

Keywords： Rhodium(III) , N-sulfonyl 2-aminobenzaldehyde , Olefin ,

开发了一种用铑(III)催化的N-磺酰基2-氨基苯甲醛与烯烃环化生成喹啉衍生物的方法,得到较高产率的喹啉衍生物,并且在反应条件下,反应具有较好的官能团兼容性。这是首次运用铑(III)作为催化剂合成烷基1-磺酰基-1,2-二氢喹啉-3-羧酸酯。该催化体系表现较好的催化性且反应操作较为简单。

We developed a new synthetic method for the production of 1,2-dihydroquinolines and quinolines via the Rh(III)-catalyzed annulation of N-sulfonyl 2-aminobenzaldehydes with olefins. Various func-tionalities were found to be compatible under the operationally simple conditions. This study pro-vides the first example of a Rh(III)-catalyzed synthesis of 1,2-dihydroquinolines.

参考文献

[1]	Eicher T;Hauptmann S.The Chemistry of Heterocycles[M].New Jersey:Wiley-VCH,2003:316.
[2]	Michael,JP .Quinoline, quinazoline and acridone alkaloids.[J].Natural Product Reports,2008(1):166-187.
[3]	Li J J.Name Reactions[M].New York:Springer-Verlag,2009:92.
[4]	Jin X K;Liu Y X;Lu Q Q;Yang D J Sun J K Qin S S Zhang J W Shen J X Chu C H Liu R H .[J].Organic and Biological Chemistry,2013,11:3776.
[5]	Read, M.L.;Gundersen, L.-L. .Synthesis of phenanthridine derivatives by microwave-mediated cyclization of o-furyl(allylamino)arenes[J].The Journal of Organic Chemistry,2013(3):1311-1316.
[6]	顾辉子,许响生,陈傲昂,严新焕.芳香硝基化合物原位液相加氢-锅法合成喹啉类化合物[J].催化学报,2012(08):1423-1426.
[7]	Meseroll L M N;McKee J R;Zanger M .[J].Synthetic Communications,2011,41:2557.
[8]	Lu, PF;Sanchez, C;Cornella, J;Larrosa, I .Silver-Catalyzed Protodecarboxylation of Heteroaromatic Carboxylic Acids[J].Organic letters,2009(24):5710-5713.
[9]	Chai D I;Lautens M .[J].Journal of Organic Chemistry,2009,74:3054.
[10]	Minville J;Poulin J;Dufresne C;Sturino C F .[J].Tetrahedron Letters,2008,49:3677.
[11]	Frotscher M;Ziegler E;Marchais Oberwinkler S;Kruchten P Neugebauer A Fetzer L Scherer C Müller Vieira U Messinger J Thole H Hartmann R W .[J].Journal of Medicinal Chemistry,2008,51:2158.
[12]	Liu ZJ;Larock RC .Highly efficient route to fused polycyclic aromatics via palladium-catalyzed aryne annulation by aryl halides[J].The Journal of Organic Chemistry,2007(26):223-232.
[13]	Hulcoop D G;Lautens M .[J].Organic Letters,2007,9:1761.
[14]	Sánchez I;Dolors Pujol M .[J].Synthesis,2006,11:1823.
[15]	He Y;Mahmud H;Moningka R;Lovely CJ;Dias HVR .Cyclization reactions of N-acryloyl-2-aminobenzaldehyde derivatives: formal total synthesis of martinellic acid[J].Tetrahedron,2006(37):8755-8769.
[16]	Muchowski J M;Maddox M L .[J].Canadian Journal of Chemistry,2004,82:461.
[17]	Katritzky AR.;Bobrov S.;Kirichenko K.;Ji Y.;Steel PJ. .Syntheses of Examples of the 5,6-dihydro-4H-[1,2,3]triazolo[4,5,1-ij]quinoline, 4,5,6,7-tetrahydro[1,2,3]triazolo[4,5,1-jk][1,4]benzodiazepine, and 5,6,7,8-tetrahydro-4H-[1,2,3]triazolo[4,5,1-kl][1]benzazocine ring systems[J].The Journal of Organic Chemistry,2003(14):5713-5719.
[18]	Wang Y;Chen C;Peng J;Li M .[J].ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2013,52:5323.
[19]	Carrigan C N;Bartlett R D;Esslinger C S;Cybulski K A Tongcharoensirikul P Bridges R J Thompson C M .[J].Journal of Medicinal Chemistry,2002,45:2260.
[20]	Kim J N;Chung Y M;Im Y J .[J].Tetrahedron Letters,2002,42:3737.
[21]	Chung Y M;Lee H J;Hwang S S;Kim J N .[J].Bulletin of the Korean Chemical Society,2001,22:799.
[22]	Migneault D;Bernstein M A;Lau C K .[J].Canadian Journal of Chemistry,1995,73:1506.
[23]	Grimshaw J;Hewitt S A .[J].J Chem Soc Perkin Trans,1990,1:2995.
[24]	Leete E .[J].Canadian Journal of Chemistry,1980,58:1806.
[25]	Kobayashi K;Takanohashi A;Himei Y;Sano T Fukamachi S Mori-kawa O Konishi H .[J].HETEROCYCLES,2007,71:2717.
[26]	Fürstner A;Mamane V;Seidel G;Laurich D .[J].Organic Syntheses,2006,83:103.
[27]	Mamane V;Hannen P;Fürstner A .[J].Chemistry-A European Journal,2004,10:4556.
[28]	Fürstner A;Mamane V .[J].Journal of Organic Chemistry,2002,67:6264.
[29]	Modak, A.;Naveen, T.;Maiti, D. .An efficient dehydroxymethylation reaction by a palladium catalyst[J].Chemical communications,2013(3):252-254.
[30]	Jiang, F.;Wu, Z.;Zhang, W. .Pd(II)-catalyzed oxidative cyclization reaction for the preparation of 2-substituted 1,2,3,4-tetrahydroquinolines with halide functionality[J].Tetrahedron,2011(7):1501-1505.
[31]	Park YS;Cho MY;Kwon YB;Yoo BW;Yoon CM .Amination of the Baylis-Hillman acetates in ethanol[J].Synthetic Communications,2007(16):2677-2685.
[32]	Ha H J;Ahn Y G;Woo J S .[J].Bulletin of the Korean Chemical Society,1998,19:818.
[33]	van der Schaaf P A;Sutter J P;Grellier M;van Mier G P M Spek A L van Koten G Pfeffer M .[J].Journal of the American Chemical Society,1994,116:5134.
[34]	Cortese N A;Ziegler C B Jr;Hrnjez B J;Heck R F .[J].Journal of Organic Chemistry,1978,43:2952.
[35]	Hegedus L S;Allen G F;Bozell J J;Waterman E L .[J].Journal of the American Chemical Society,1978,100:5800.
[36]	Watanabe Y;Suzuki N;Tsuji Y;Shim S C Mitsudo T .[J].Bul Chem Soc Jpn,1982,55:1116.
[37]	Watanabe Y;Suzuki N;Shim S C;Yamamoto M,Mitsudo T,Takegami Y.[J].Chem Lett,1980:429.
[38]	Watanabe Y;Yamamoto M;Shim S C;Mitsudo T,Takegami Y.[J].Chem Lett,1979:1025.
[39]	Diamond S E;Szalkiewicz A;Mares F .[J].Journal of the American Chemical Society,1979,101:490.
[40]	Boyle W J Jr;Mares F .[J].ORGANOMETALLICS,1982,1:1003.
[41]	Watanabe Y;Shim S C;Mitsudo T .[J].Bulletin of the Chemical Society of Japan,1981,54:3460.
[42]	Song G Y;Gong X;Li X W .[J].Journal of Organic Chemistry,2011,76:7583.
[43]	Abbiati G;Arcadi A;Marinelli F;Rossi E;Verdecchia M .Rh-catalyzed sequential hydroarylation/hydrovinylation-heterocyclization of beta-(2-aminophenyl)-alpha,beta-ynones with organoboron derivatives: A new approach to functionalized quinolines[J].Synlett,2006(19):3218-3224.
[44]	Zhou, J.;Li, B.;Hu, F.;Shi, B.-F. .Rhodium(III)-catalyzed oxidative olefination of pyridines and quinolines: Multigram-scale synthesis of naphthyridinones[J].Organic letters,2013(13):3460-3463.
[45]	Bennasar ML;Roca T;Monerris M;Garcia-Diaz D .Sequential N-acylamide methylenation-enamide ring-closing metathesis: Construction of benzo-fused nitrogen heterocycles[J].The Journal of Organic Chemistry,2006(18):7028-7034.
[46]	Cho C S;Kim B T;Kim T J;Shim S C.[J].Chem Commun,2001:2576.
[47]	Cho C S;Oh B H;Kim J S;Kim T J,Shim S C.[J].Chem Commun,2000:1885.
[48]	Tsuji Y;Huh K T;Watanabe Y .[J].Journal of Organic Chemistry,1987,52:1673.
[49]	Watanabe Y;Tsuji Y;Shida J .[J].Bulletin of the Chemical Society of Japan,1984,57:435.
[50]	Watanabe Y;Tsuji Y;Ohsugi Y;Shida J .[J].Bulletin of the Chemical Society of Japan,1983,56:2452.
[51]	Cho C S;Kim D T;Kim T J;Shim S C .[J].Bulletin of the Korean Chemical Society,2003,24:1026.
[52]	Watanabe Y;Tsuji Y;Suzuki N.[J].Chem Lett,1981:1067.
[53]	Jung C W;Fellmann J D;Garrou P E .[J].ORGANOMETALLICS,1983,2:1042.
[54]	Watanabe Y;Takatsuki K;Shim S C;Mitsudo T Takegami Y .[J].Bulletin of the Chemical Society of Japan,1978,51:3397.
[55]	Barluenga J;Fa?anás F J;Sanz R;Fernández Y .[J].Chemistry-A European Journal,2002,8:2034.
[56]	Niu Q S;Mao H;Yuan G D;Gao J L Liu H Q Tu Y W Wang X X Lv X .[J].Advanced Synthesis and Catalysis,2013,355:1185.
[57]	Petu?kova J;Bruns H;Alcarazo M .[J].ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2011,50:3799.
[58]	Colby, DA;Bergman, RG;Ellman, JA .Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation[J].Chemical Reviews,2010(2):624-655.
[59]	Alberico D;Scott M E;Lautens M .[J].CHEMICAL REVIEWS,2007,107:174.
[60]	Zhang T;Qi Z S;Zhang X Y;Wu L M Li X W .[J].Chemistry-A European Journal,2014,20:3283.
[61]	Fonseca MH.;Eibler E.;Zabel M.;Konig B. .Synthesis of novel nitrogen-containing ligands for the enantioselective addition of diethylzinc to aldehydes[J].Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry,2003(14):1989-1994.

上一张下一张

计量

下载量()
访问量()

作者相关

文章评分

您的评分：
1

0%
2

0%
3

0%
4

0%
5

0%

材料期刊网