中文
Earlier issues
Announcement
More
Progress in Chemistry 2019, Vol. 31 Issue (10): 1362-1371 DOI: 10.7536/PC190519 Previous Articles   Next Articles

Application of Ugi/Diels-Alder Tandem Reaction in the Construction of Heterocyclic Compounds

Tianyi Shang1, Qiyan Lv2, Yan Liu1,**(), Bing Yu2,**()   

  1. 1. College of Biological and Pharmaceutical Engineering, Xinyang Agriculture and Forestry University, Xinyang 464000, China
    2. College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001, China
  • Received: Online: Published:
  • Contact: Yan Liu, Bing Yu
  • About author:
    ** E-mail: (Yan Liu);
    (Bing Yu)
  • Supported by:
    National Natural Science Foundation of China(21501010); China Postdoctoral Science Foundation(2019M652561); Key Research Project of Higher Education Institutions in Henan Province(20B150021); Research Fund of Xinyang Agriculture and Forestry University for Young Teachers(201701009)
Richhtml ( 21 ) PDF ( 1621 ) Cited
Export

EndNote

Ris

BibTeX

Heterocyclic compounds are widely present in natural products and drug molecules and many of them also have potential biological activities and pharmacological effects. Therefore, methodologies toward rapid and efficient construction of heterocyclic compound libraries have become one of the research hotspots in the fields of organic synthesis and pharmaceutical chemistry. Ugi reaction has unique advantages in diversity-oriented synthesis to generate a large number of target products with structural complexity. Meanwhile, Diels-Alder [4+2] cycloaddition reaction can efficiently form carbon-carbon bonds to access various heterocyclic rings with good stereo- and region-selectivity. Nowadays, Ugi/Diels-Alder tandem reaction, which combine merits of the two, presents enormous advantages and infinite potential in synthesis of heterocyclic compounds. In this paper, the recent advances in Ugi/Diels-Alder tandem reaction is summarized and reviewed according to the types of dienes in DA reactions, such as furan, pyrrole, thiophene, oxazole, 1,2,4-triazine, benzene, and unsaturated bond with aromatic ring.

Key words: heterocyclic compounds, Ugi reaction, Diels-Alder reaction, tandem reaction
Scheme. 1 Classical Ugi four-component reaction
Fig. 1 Construction of heterocyclic compounds via intramolecular bifunctional groups in Ugi adducts
Scheme. 2 Synthesis of 2 and 3 via UDA tandem reaction[35, 36]
Scheme. 3 A UDA/deselenization/aromatization sequence[37]
Scheme. 4 Synthesis of 6 via US/IMDA tandem reaction[39]
Scheme. 5 Solid phase synthesis of 8 via UDA tandem reaction[35]
Scheme. 6 通过UDA串联反应固相合成化合物11[40]
Scheme. 7 Solid phase synthesis of 14 via UDA tandem reaction[41]
Scheme. 8 Synthesis of 19 via UDA tandem reaction[42]
Scheme. 9 Synthesis of 22 via UDA tandem reaction[44]
Scheme. 10 UDA tandem reaction formula via addition of the alkyne and pyrrole[44, 45]
Scheme. 11 Synthesis of 24 via UDA tandem reaction[46]
Scheme. 12 Synthesis of polysubstituted oxazole via three component reaction[49,50,51,52]
Scheme. 13 Synthesis of 27 via UDA tandem reaction[55]
Scheme. 14 Synthesis of 29 via UDA tandem reaction[53]
Scheme. 15 Synthesis of HMBA via UDA tandem reaction[56]
Scheme. 16 Synthesis of 30 via UDA tandem reaction[54]
Scheme. 17 Synthesis of 34 via UDA tandem reaction[57]
Scheme. 18 Synthesis of 35 via UDA tandem reaction[58]
Scheme. 19 Synthesis of 36 via UDA tandem reaction[59]
Scheme. 20 Synthesis of 39 via UDA tandem reaction[60]
Scheme. 21 Synthesis of 40 via UDA tandem reaction[61]
Scheme. 22 Ugi/Diels-Alder/HCl elimination donimo reaction[62]
Scheme. 23 Synthesis of 42 via Ugi/retro Diels-Alder tandem reaction[63]
[1]
Dömling A, Ugi I . Angew. Chem. Int. Ed., 2000,39:3168.
[2]
Zhu J . Eur. J. Org. Chem., 2003,2003:1133.
[3]
Domling A . Chem. Rev., 2006,106:17.
[4]
Cioc R C, Ruijter E, Orru R V A . Green Chem., 2014,16:2958.
[5]
Brauch S, van Berkel S S, Westermann B . Chem. Soc. Rev., 2013,42:4948.
[6]
Domling A, Wang W, Wang K . Chem. Rev., 2012,112:3083.
[7]
Sunderhaus J D, Martin S E . Chem. Eur. J., 2009,15:1300.
[8]
Schreiber S L . Science, 2000,287:1964.
[9]
Burke M D, Schreiber S L . Angew. Chem. Int. Ed., 2004,43:46.
[10]
Tan D S . Nature Chemical Biology, 2005,1:74.
[11]
Nielsen T E, Schreiber S L . Angew. Chem. Int. Ed., 2008,47:48.
[12]
Galloway W R, Isidro-Llobet A, Spring D R . Nat. Commun., 2010,1:80.
[13]
Corey E J . Angew. Chem. Int. Ed., 2002,41:1650.
[14]
Nicolaou K C, Snyder S A, Montagnon T, Vassilikogiannakis G . Angew. Chem. Int. Ed., 2002,41:1668.
[15]
Notz W, Tanaka F, Barbas C F . Acc. Chem. Res., 2004,37:580.
[16]
Takao K, Munakata R, Tadano K . Chem. Rev., 2005,105:4779.
[17]
Kouznetsov V V . Tetrahedron, 2009,65:2721.
[18]
Simoni D, Roberti M, Invidiata F P, Rondanin R, Baruchello R, Malagutti C, Mazzali A, Rossi M, Grimaudo S, Capone F, Dusonchet L, Meli M, Raimondi M V, Landino M, D’Alessandro N, Tolomeo M, Arindam D, Lu S, Benbrook D M . J. Med. Chem., 2001,44:2308.
[19]
Kidwai M, Venkataramanan R, Mohan R, Sapra P . Curr. Med. Chem., 2002,9:1209.
[20]
St Jean D J, Fotsch C . J. Med. Chem., 2012,55:6002.
[21]
Stepien M, Gonka E, Zyla M, Sprutta N . Chem. Rev., 2017,117:3479.
[22]
Liu Y, Chen X L, Zeng F L, Sun K, Qu C, Fan L L, An Z L, Li R, Jing C F, Wei S K, Qu L B, Yu B, Sun Y Q, Zhao Y F . J. Org. Chem., 2018,83:11727.
[23]
Liu Y, Chen X L, Sun K, Li X Y, Zeng F L, Liu X C, Qu L B, Zhao Y F, Yu B . Org. Lett., 2019,21:4019.
[24]
Lu K, Ma Y, Gao M, Liu Y, Li M, Xu C, Zhao X, Yu P . Org. Lett., 2016,18:5038.
[25]
Gao X, Shan C, Chen Z, Liu Y, Zhao X, Zhang A, Yu P, Galons H, Lan Y, Lu K . Org. Biomol. Chem., 2018,16:6096.
[26]
Li X, Jia X, Yin L . Chin. J. Org. Chem., 2017,37:2237.
[27]
Bariwal J, Kaur R, Voskressensky L G, van der Eycken E V . Frontiers in Chemistry, 2018,6:557.
[28]
Modha S G, Kumar A, Vachhani D D, Jacobs J, Sharma S K, Parmar V S, van Meervelt L, van der Eycken E V . Angew. Chem. Int. Ed., 2012,51:9572.
[29]
Sharma N, Li Z, Sharma U K, van der Eycken E V . Org. Lett., 2014,16:3884.
[30]
Xiang Z, Luo T P, Lu K, Cui J Y, Shi X M, Fathi R, Chen J H, Yang Z . Org. Lett., 2004,6:3155.
[31]
Santra S, Andreana P R . Angew. Chem. Int. Ed., 2011,50:9418.
[32]
Ramazani A, Rezaei A . Org. Lett., 2010,12:2852.
[33]
Chapman T M, Davies I G, Gu B, Block T M, Scopes D I C, Hay P A, Courtney S M, McNeill L A, Schofield C J, Davis B G . J. Am. Chem. Soc., 2005,127:506.
[34]
Bonnaterre F, Bois-Choussy M, Zhu J . Org. Lett., 2006,8:4351.
[35]
Paulvannan K . Tetrahedron Lett., 1999,40:1851.
[36]
Caillot G, Hegde S, Gras E . New J. Chem., 2013,37:1195.
[37]
Huang X, Xu J . J. Org. Chem., 2009,74:8859.
[38]
El Kaim L, Grimaud L, Oble J . Angew. Chem. Int. Ed., 2005,44:7961.
[39]
Richey B, Mason K M, Meyers M S, Luesse S B . Tetrahedron Lett., 2016,57:492.
[40]
Lee D, Sello J K, Schreiber S L . Org. Lett., 2000,2:709.
[41]
Oikawa M, Ikoma M, Sasaki M . Tetrahedron Lett., 2005,46:415.
[42]
Wright D L, Robotham C V, Aboud K . Tetrahedron Lett., 2002,43:943.
[43]
Gordon C P, Young K A, Robertson M J, Hill T A, McCluskey A . Tetrahedron, 2011,67:554.
[44]
Paulvannan K . J. Org. Chem., 2004,69:1207.
[45]
Kajanus J, Jacobson I, Åstrand A, Olsson R I, Gran U, Björe A, Fjellström O, Davidsson Ö, Emtenäs H, Dahlen A . Bioorg. Med. Chem. Lett., 2016,26:2023.
[46]
Santra S, Andreana P R . Org. Lett., 2007,9:5035.
[47]
Zhang T C, Nakajima M . Advances in Applied Biotechnology. 1st ed. Berlin: Springer, 2015. 461.
[48]
Sun X, Janvier P, Zhao G, Bienaymé H, Zhu J . Org. Lett., 2001,3:877.
[49]
González-Zamora E, Fayol A, Bois-Choussy M, Chiaroni A, Zhu J . Chem. Commun., 2001,1684.
[50]
Janvier P, Sun X, Bienaymé H, Zhu J . J. Am. Chem. Soc., 2002,124:2560.
[51]
Lalli C, Bouma M J, Bonne D, Masson G, Zhu J . Chem. Eur. J., 2011,17:880.
[52]
Su Y, Bouma M J, Alcaraz L, Stocks M, Furber M, Masson G, Zhu J . Chem. Eur. J., 2012,18:12624.
[53]
Islas-Jácome A, González-Zamora E, Gámez-Montaño R . Tetrahedron Lett., 2011,52:5245.
[54]
Xia L, Li S, Chen R, Liu K, Chen X . J. Org. Chem., 2013,78:3120.
[55]
Fayol A, Housseman C, Sun X, Janvier P, Bienayme H, Zhu J . Synthesis, 2005,2005:161.
[56]
Zamudio-Medina A, García-González M C, Gutierrez-Carrillo A, González-Zamora E . Tetrahedron Lett., 2015,56:627.
[57]
Janvier P, Bienaymé H, Zhu J . Angew. Chem. Int. Ed., 2002,41:4291.
[58]
Akritopoulou-Zanze I, Wang Y, Zhao H, Djuric S W . Tetrahedron Lett., 2009,50:5773.
[59]
Cheng G, He X, Tian L, Chen J, Li C, Jia X, Li J . J. Org. Chem., 2015,80:11100.
[60]
Lu K, Luo T, Xiang Z, You Z, Fathi R, Chen J, Yang Z . J. Comb. Chem., 2005,7:958.
[61]
Ambasana P A, Vachhani D D, Galli M, Jacobs J, van Meervelt L, Shah A K, van der Eycken E V . Org. Biomol. Chem., 2014,12:8861.
[62]
Huang J, Du X, van Hecke K, van der Eycken E V, Pereshivko O P, Peshkov V A . Eur. J. Org. Chem., 2017,2017:4379.
[63]
Basso A, Banfi L, Riva R, Guanti G . Tetrahedron Lett., 2004,45:587.
[64]
Oikawa M, Ikoma M, Sasaki M, Gill M B, Swanson G T, Shimamoto K, Sakai R . Eur. J. Org. Chem., 2009,2009:5531.
[65]
Ikoma M, Oikawa M, Sasaki M . Eur. J. Org. Chem., 2009,2009:72.
[66]
Oikawa M, Ikoma M, Sasaki M . Tetrahedron Lett., 2005,46:5863.
[67]
Ilyin A, Kysil V, Krasavin M, Kurashvili I, Ivachtchenko A V . J. Org. Chem., 2006,71:9544.
[68]
Sello J K,, reana P R, Lee D, Schreiber S L . Org. Lett., 2003,5:4125.
[1] Peng Wang, Huan Liu, Da Yang. Recent Advances on Tandem Hydroformylation of Olefins [J]. Progress in Chemistry, 2022, 34(5): 1076-1087.
[2] Yaqi Wang, Qiang Wu, Junling Chen, Feng Liang. Diels-Alder Reaction Catalyst [J]. Progress in Chemistry, 2022, 34(2): 474-486.
[3] Yujue Wang, Min Hu, Xiao Li, Nan Xu. Chemical Composition, Sources and Formation Mechanisms of Particulate Brown Carbon in the Atmosphere [J]. Progress in Chemistry, 2020, 32(5): 627-641.
[4] Lingbin Kong, Shengjiao Yan*, Jun Lin*. Heterocyclic Ketene Aminals: Leading Molecules to Construct Molecular Diversity Fused Heterocyclic Compounds [J]. Progress in Chemistry, 2018, 30(5): 639-657.
[5] Kun Cao, Bei Yuan, Xue Liu, Minfang Wu, Zhen Yao*. Preparation and Applications of the Chiral Norbornene Derivatives [J]. Progress in Chemistry, 2017, 29(6): 605-616.
[6] Zhang Bianxiang*, Zhao Xiaoyun, Wu Qun, Guo Yili. Application of Diaryliodonium Salts in Arylation Reaction [J]. Progress in Chemistry, 2013, 25(07): 1142-1148.
[7] Zhang Wensheng, Li Wei, Kuang Chunxiang. Application of 1,1-Dibromo-2-Arylalkene in Cyclization Reaction [J]. Progress in Chemistry, 2013, 25(07): 1149-1157.
[8] Wang Zhipeng, Yuan Jinying* . Applications of Diels-Alder Reaction in Synthesis of Polymers with Well-Defined Architectures [J]. Progress in Chemistry, 2012, 24(12): 2342-2351.
[9] Zhao Ping1,Yin Yingwu1,2**. Development of the Anodic Cyanation Reaction [J]. Progress in Chemistry, 2004, 16(06): 926-.
[10] Ma Ning,Li Zhengming*,Zhao Weiguang. Progress in Ugi Reaction [J]. Progress in Chemistry, 2003, 15(03): 186-.