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Synthesis 2023; 55(07): 1007-1041
DOI: 10.1055/s-0042-1751418
review

Sugars in Multicomponent Reactions: A Toolbox for Diversity-Oriented Synthesis

Vipin K. Maikhuri‡
a   Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi, India
,
Vineet Verma‡
a   Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi, India
b   Department of Chemistry, Starex University, Gurugram, Haryana, India
,
Ankita Chaudhary
c   Maitreyi College, Department of Chemistry, University of Delhi, Delhi, India
,
Divya Mathur  ∗
a   Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi, India
d   Daulat Ram College, Department of Chemistry, University of Delhi, Delhi, India
,
Rajesh Kumar
e   Department of Chemistry, R.D.S. College, B.R.A. Bihar University, Muzaffarpur, India
,
Ashok K. Prasad∗
a   Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi, India
› Author AffiliationsWe are grateful to the Institute of Eminence, University of Delhi for providing financial support under R&D program.
› Further Information
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Abstract

Multicomponent reactions (MCRs) cover strategically employed chemical transformations that incorporate three or more reactants in one pot leading to a functionalized final product. Thus, it is an ideal tool to achieve high levels of complexity, diversity, yields of desired products, atom economy, and reduced reaction times. Sugars belong to the class of naturally occurring compounds with fascinating applications in the field of drug discovery due to the presence of various hydroxy groups and well-defined stereochemistry. However, their potential in MCRs has been realized only recently. This account describes recent advances in the synthesis of sugar-derived heterocycles synthesized by MCRs. We hope to encourage the synthetic and medicinal chemistry community to apply this powerful MCR chemistry to generate novel glycoconjugate challenges.

1 Introduction

2 Synthesis of Various Functionalized Sugar Compounds

2.1 Passerini and Ugi Multicomponent Reactions

2.2 Petasis Reaction

2.3 Hantzsch Reaction

2.4 Domino Ferrier–Povarov Reaction

2.5 Marckwald Reaction

2.6 Groebke–Blackburn–Bienaymé (GBB) Reaction

2.7 Prins–Ritter Reaction

2.8 Debus–Radziszewski Imidazole Synthesis Reaction

2.9 Mannich Reaction

2.10 A3-Coupling Reaction

2.11 [3+2]-Cycloaddition Reactions

2.12 Miscellaneous Reactions

3 Conclusion

Key words

sugars - multicomponent reactions - isocyanides - aldehydes - domino reactions


Publication History

Received: 22 November 2022

Accepted after revision: 17 January 2023

Article published online:
02 March 2023

© 2023. Thieme. All rights reserved

Georg Thieme Verlag KG
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  • References

    • 1a Reguera L, Rivera DG. Chem. Rev. 2019; 119: 9836
      CrossrefPubMed
    • 1b Longo LS, Siqueira FA, Anjos NS, Santos GF. D. ChemistrySelect 2021; 6: 5097
      Crossref
    • 1c Bakulina O, Inyutina A, Dar’in D, Krasavin M. Molecules 2021; 26: 6563
      CrossrefPubMed
    • 1d Rodriguez PN, Ghashghaei O, Bagan A, Escolano C, Lavilla R. Biomedicine 2022; 10: 1488
    • 1e Multicomponent Reactions . Zhu J, Bienaymé H. Wiley-VCH; Weinheim: 2005
      Google Scholar
    • 1f Multicomponent Reactions: Concepts and Applications for Design and Synthesis. Herrera RP, Marqués-López E. John Wiley & Sons; Hoboken: 2015
      Google Scholar
  • 2 Posner GH. Chem. Rev. 1986; 86: 831
    Crossref
    • 3a Zarganes-Tzitzikas T, Chandgude AL, Dömling A. Chem. Rec. 2015; 15: 981
      CrossrefPubMed
    • 3b Brandao P, Marques C, Burke AJ, Pineiro M. Eur. J. Med. Chem. 2021; 211: 113102
      CrossrefPubMed
  • 4 Ugi I. Pure Appl. Chem. 2001; 73: 187
    CrossrefPubMed
    • 5a Domling A, Wang W, Wang K. Chem. Rev. 2011; 112: 3083
      CrossrefPubMed
    • 5b Zhi S, Ma X, Zhang W. Org. Biomol. Chem. 2019; 17: 7632
      CrossrefPubMed
    • 5c Olyaei A, Abediha S, Sadeghpour M, Adl A. ChemistrySelect 2022; 7: e202201650
      Crossref
    • 5d Bosica G, Demanuele K, Padrón JM, Puerta A. Beilstein J. Org. Chem. 2020; 16: 2862
      CrossrefPubMed
    • 5e Giustiniano M, Moni L, Sangaletti L, Pelliccia S, Basso A, Novellino E, Tron GC. Synthesis 2018; 50: 3549
      Article in Thieme Connect
    • 6a Tietze LF, Brasche G, Gericke KM. Domino Reactions in Organic Synthesis . Wiley-VCH; Weinheim: 2006
      CrossrefGoogle Scholar
    • 6b Domino Reactions: Concepts for Efficient Organic Synthesis. Tietze LF. Wiley-VCH; Weinheim: 2014
      Google Scholar
  • 7 Müller TJ. J, D’Souza D. Pure Appl. Chem. 2008; 80: 609
    Crossref
    • 9a Hunter CD, Guo T, Daskhan G, Richards MR, Cairo CW. Chem. Rev. 2018; 118: 8188
      CrossrefPubMed
    • 9b Su L, Feng Y, Wei K, Xu X, Liu R, Chen G. Chem. Rev. 2021; 121: 10950
      CrossrefPubMed
  • 10 Jiang H, Qin X, Wang Q, Xu Q, Wang J, Wu Y, Chen W, Wang C, Zhang T, Xing D, Zhang R. Eur. J. Med. Chem. 2021; 223: 113633
    CrossrefPubMed
  • 12 Chan-Tack KM, Kim C, Moruf A, Birnkrant DB. Antiviral Ther. 2015; 20: 561
    CrossrefPubMed
  • 13 Chen C, Lu L, Yan S, Yi H, Yao H, Wu D, He G, Tao X, Deng X. Anticancer Drugs 2018; 29: 1
    CrossrefPubMed
  • 14 Saeed MA, Narendran P. Drug Des., Dev. Ther. 2014; 8: 2493
    CrossrefPubMed
  • 15 Yilmaz C, Ozcengiz G. Biochem. Pharmacol. 2017; 133: 43
    CrossrefPubMed
  • 16 Aoki T, Kokudo N, Komoto I, Takaori K, Kimura W, Sano K, Takamoto T, Hashimoto T, Okusaka T, Morizane C, Ito T, Imamura M. J. Gastroenterol. 2015; 50: 769
    CrossrefPubMed
  • 17 Eastman RT, Roth JS, Brimacombe KR, Simeonov A, Shen M, Patnaik S, Hall MD. ACS Cent. Sci. 2020; 6: 672
    CrossrefPubMed
    • 18a Lockhoff O. Angew. Chem. Int. Ed. 1998; 37: 3436
      CrossrefPubMed
    • 18b Khan MM, Yousuf R, Khan S. Shafiullah, RSC Adv. 2015; 5: 57883
      Crossref
    • 19a Wahby Y, Abdel-Hamid H, Ayoup MS. New J. Chem. 2022; 46: 1445
      Crossref
    • 19b Passerini M. Gazz. Chim. Ital. 1921; 51: 126
      CrossrefPubMed
    • 20a Mohammadkhani L, Heravi MM. ChemistrySelect 2019; 4: 10187
      Crossref
    • 20b Tripolitsiotis NP, Thomaidi M, Neochoritis CG. Eur. J. Org. Chem. 2020; 2020: 6525
      Crossref
  • 21 Ramozzi R, Morokuma K. J. Org. Chem. 2015; 80: 5652
    CrossrefPubMed
    • 22a Tsai CY, Park WK, Weitz-Schmidt G, Ernst B, Wong CH. Bioorg. Med. Chem. Lett. 1998; 8: 2333
      CrossrefPubMed
    • 22b Sutherlin DP, Stark TM, Hughes R, Armstrong RW. J. Org. Chem. 1996; 61: 8350
      CrossrefPubMed
  • 23 Westermann B, Dörner S. Chem. Commun. 2005; 2116
    CrossrefPubMed
  • 24 Vlahovicek-Kahlina K, Vazdar M, Jakas A, Smrecki V, Jeric I. J. Org. Chem. 2018; 83: 13146
    CrossrefPubMed
  • 25 Vlahovicek-Kahlina K, Sajko JS, Jeric I. Int. J. Mol. Sci. 2019; 20: 6236
    CrossrefPubMed
  • 26 Esen E, Meier MA. R. ACS Sustainable Chem. Eng. 2020; 8: 15755
    CrossrefPubMed
  • 27 Dinh TQ, Smith CD, Du X, Armstrong RW. J. Med. Chem. 1998; 41: 981
    CrossrefPubMed
  • 28 Kumar B, Maity J, Shankar B, Kumar S, Kavita, Prasad AK. Carbohydr. Res. 2021; 500: 108236
    CrossrefPubMed
  • 29 Azad CS, Saxena AK. Org. Chem. Front. 2015; 2: 665
    CrossrefPubMed
  • 30 Wang H, Shen Y, Zhao L, Ye Y. Curr. Med. Chem. 2021; 28: 628
    CrossrefPubMed
  • 31 Fleet GW. J, Estevez JC, Smith MD, Blériot Y, la Fuente C, Krülle TM, Besra GS, Brennan PJ, Nash RJ, Johnson LN, Oikonomakos NG. Pure Appl. Chem. 1998; 70: 279
    CrossrefPubMed
  • 32 Voigt B, Linke M, Mahrwald R. Org. Lett. 2015; 17: 2606
    CrossrefPubMed
  • 33 Zhao P.-F, Liu Z.-Q. Eur. J. Med. Chem. 2017; 135: 458
    CrossrefPubMed
  • 34 Vlahovicek-Kahlina K, Stefanic Z, Vazdar K, Jeric I. ChemPlusChem 2020; 85: 838
    CrossrefPubMed
  • 35 Jakas A, Visnjevac A, Jeric I. J. Org. Chem. 2020; 85: 3766
    CrossrefPubMed
  • 36 Jakas A, Ayyalasomayajula R, Cudic M, Jerić I. Glycoconjugate J. 2022; 39: 587
    CrossrefPubMed
  • 37 Wieclaw MM, Furman B. Beilstein J. Org. Chem. 2021; 17: 115
    CrossrefPubMed
  • 38 Kumar H, Prajapati G, Dubey A, Ampapathi RS, Mandal PK. Org. Lett. 2020; 22: 9258
    CrossrefPubMed
  • 39 Mendez Y, Chang J, Humpierre AR, Zanuy A, Garrido R, Vasco AV, Pedroso J, Santana D, Rodriguez LM, Garcia-Rivera D, Valdes Y, Verez-Bencomo V, Rivera DG. Chem. Sci. 2018; 9: 2581
    CrossrefPubMed
  • 40 Wu P, Givskov M, Nielsen TE. Chem. Rev. 2019; 119: 11245
    CrossrefPubMed
  • 41 Tao C.-Z, Zhang Z.-T, Wu J.-W, Li R.-H, Cao Z.-L. Chin. Chem. Lett. 2014; 25: 532
    CrossrefPubMed
  • 42 Lenci E, Puglielli RB, Bucaletti E, Innocenti R, Trabocchi A. Eur. J. Org. Chem. 2020; 2020: 4227
    CrossrefPubMed
  • 43 Dondoni A, Massi A. Mol Diversity 2003; 6: 261
    CrossrefPubMed
  • 44 Dondoni A, Massi A, Minghini E. Synlett 2002; 0089
    Article in Thieme ConnectPubMed
  • 45 Verma C, Quraishi MA, Kluza K, Makowska-Janusik M, Olasunkanmi LO, Ebenso EE. Sci. Rep. 2017; 7: 44432
    CrossrefPubMed
  • 46 Nourisefat M, Panahi F, Khalafi-Nezhad A. Mol. Diversity 2019; 23: 317
    CrossrefPubMed
  • 47 Nikoofar K, Heidari H, Shahedi Y. Cellulose 2018; 25: 5697
    CrossrefPubMed
  • 48 Gupta S, Khare NK. J. Mol. Struct. 2017; 1127: 309
    CrossrefPubMed
  • 49 Verma C, Olasunkanmi LO, Ebenso EE, Obot IB, Quraishi MA. J. Phys. Chem. C 2016; 120: 11598
    CrossrefPubMed
  • 50 Gomez AM, Lobo F, Uriel C, Lopez JC. Eur. J. Org. Chem. 2013; 2013: 7221
    CrossrefPubMed
  • 51 Moshapo PT, Sokamisa M, Mmutlane EM, Mampa RM, Kinfe HH. Org. Biomol. Chem. 2016; 14: 5627
    CrossrefPubMed
  • 52 Baumann M, Baxendale IR. Org. Lett. 2014; 16: 6076
    CrossrefPubMed
  • 53 Kumar B, Shankar B, Kumar S, Maity J, Prasad AK. Synth. Commun. 2020; 50: 2853
    CrossrefPubMed
  • 54 Chiba M, Ishikawa Y, Sakai R, Oikawa M. ACS Comb. Sci. 2016; 18: 399
    CrossrefPubMed
  • 55 Petrusova M, Smrticova H, Pribulova B, Vlckova S, Uhliarikova I, Docsa T, Somsak L, Petrus L. Tetrahedron 2016; 72: 2116
    CrossrefPubMed
  • 56 Allochio Filho JF, Lemos BC, de Souza AS, Pinheiro S, Greco SJ. Tetrahedron 2017; 73: 6977
    CrossrefPubMed
  • 57 Rajasekar M, Das TM. RSC Adv. 2014; 4: 42538
    CrossrefPubMed
  • 58 Thakur K, Khare NK. Carbohydr. Res. 2020; 494: 108053
    CrossrefPubMed
  • 59 Mondal RR, Khamarui S, Maiti DK. ACS Omega 2016; 1: 251
    CrossrefPubMed
  • 60 Mandal PK. RSC Adv. 2014; 4: 5803
    Crossref
  • 61 Xie J, Bogliotti N. Chem. Rev. 2014; 114: 7678
    CrossrefPubMed
  • 62 Rao JN. S, Raghunathan R. Tetrahedron Lett. 2015; 56: 2669
    CrossrefPubMed
  • 63 Bellucci MC, Volonterio A. Eur. J. Org. Chem. 2014; 2014: 2386
    Crossref
  • 64 Sganappa A, Bellucci MC, Nizet V, Tor Y, Volonterio A. Synthesis 2016; 48: 4443
    Article in Thieme ConnectPubMed
  • 65 Senthilkumar S, Prasad SS, Das A, Baskaran S. Chem. Eur. J. 2015; 21: 15914
    CrossrefPubMed
  • 66 Prasad SS, Senthilkumar S, Srivastava A, Baskaran S. Org. Lett. 2017; 19: 4403
    CrossrefPubMed
  • 67 Prasad SS, Reddy NR, Baskaran S. J. Org. Chem. 2018; 83: 9604
    CrossrefPubMed
  • 68 Benmahdjoub S, Ibrahim N, Benmerad B, Alami M, Messaoudi S. Org. Lett. 2018; 20: 4067
    CrossrefPubMed
  • 69 Rao JN. S, Raghunathan R. Tetrahedron Lett. 2015; 56: 1539
    Crossref
  • 70 Xia M, Lambu MR, Tatina MB, Judeh ZM. A. J. Org. Chem. 2021; 86: 837
    CrossrefPubMed
  • 71 Rai VK, Kosta RK. Can. J. Chem. 2016; 94: 827
    CrossrefPubMed
  • 72 Dangolani SK, Panahi F, Tavaf Z, Nourisefat M, Yousefi R, Khalafi-Nezhad A. ACS Omega 2018; 3: 10341
    CrossrefPubMed
  • 73 Bellucci MC, Sagnappa A, Saini M, Volonterio A. Tetrahedron 2015; 71: 7630
    CrossrefPubMed
  • 74 Dharma Rao GB, Anjaneyulu B, Kaushik MP. Tetrahedron Lett. 2014; 55: 19
    Crossref
  • 75 Prasanna R, Puroshothaman S, Raghunathan R. Tetrahedron 2020; 76: 131398
    Crossref
  • 76 Rajput VK, Leffler H, Nilsson UJ, Mukhopadhyay B. Bioorg. Med. Chem. Lett. 2014; 24: 3516
    CrossrefPubMed
  • 77 Du L.-H, Chen P.-F, Long R.-J, Xue M, Luo XP. RSC Adv. 2020; 10: 13252
    CrossrefPubMed