Download PDF
Synthesis 2024; 56(13): 2084-2092
DOI: 10.1055/s-0043-1774905
paper

Iodine(III)-Mediated Ring-Contraction Reactions Using Halogenated and Non-halogenated Solvents

Ajmir Khan  ∗
a   School of Packaging, Michigan State University, 448 Wilson Road, East Lansing, MI 48824-1223, URL: khanajmi@msu.edu
b   Department of Fundamental Chemistry, Institute of Chemistry, University of São Paulo, Av. Prof. Lineu Prestes, 748, São Paulo, SP CEP 05508-000, Brazil
,
Umar Nishan∗
c   Department of Chemistry, Kohat University of Science and Technology, Kohat 26000 KP, Pakistan
,
Amir Badshah
c   Department of Chemistry, Kohat University of Science and Technology, Kohat 26000 KP, Pakistan
,
Riaz Ullah
d   Department of Pharmacognosy, College of Pharmacy, King Saud University, Riyadh, Saudi Arabia
,
Essam A. Ali
e   Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh, Saudi Arabia
› Author AffiliationsThe authors thank the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES), Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP), Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) and the Institute of Chemistry, University of São Paulo, Brazil. This research work was supported by Researchers Supporting Project Number (RSP2024R45) at King Saud University, Riyadh, Saudi Arabia.
› Further Information
    Permissions and Reprints All articles of this category


Luiz F. Silva Jr. In memoriam.

Abstract

The transformation of a six-membered ring into the corresponding five-membered product is an important synthetic approach used in medicinal chemistry and industrial technologies. However, the yield of the product obtained through a simple one-step reaction is lower in some reported solvent systems. Here, we present the ring contraction of 1,2-dihydronaphthalene derivatives into the corresponding indanes­ using an environmentally friendly reagent hydroxy(tosyloxy)iodobenzene (HTIB). This transformation is achieved in both non-halogenated and halogenated solvents. We show that the halogenated solvent system not only increased the yield of the anticipated product but also reduced the formation of by-products. This study delivers an important development regarding the effectiveness of hypervalent iodine reagents in halogenated and non-halogenated solvents for ring-contraction reactions.

Key words

six-membered rings - ring contraction - HTIB - five-membered rings - halogenated solvents

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2204-8461.
  • Supporting Information


Publication History

Received: 24 March 2024

Accepted after revision: 14 May 2024

Article published online:
28 May 2024

© 2024. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References

  • 1 Silva LF. Jr. Synlett 2014; 25: 466
    Article in Thieme Connect
  • 2 Khan A, Silva LF, Rabnawaz M. New J. Chem. 2021; 45: 2078
    Crossref
  • 3 Hong AY, Krout MR, Jensen T, Bennett NB, Harned AM, Stoltz BM. Angew. Chem. Int. Ed. 2011; 50: 2756 ; Angew. Chem. 2011, 123, 2808
    CrossrefPubMed
  • 4 Silva LF. Jr. Stereosel. Synth. Drugs Nat. Prod. 2013; 1
  • 5 Redmore D, Gutsche CD. Adv. Alicyclic Chem. 1971; 3: 1
    Crossref
  • 6 Meier H, Zeller K. Angew. Chem., Int. Ed. Engl. 1975; 14: 32
    Crossref
  • 7 Xu Z, Chen H, Wang Z, Ying A, Zhang L. J. Am. Chem. Soc. 2016; 138: 5515
    CrossrefPubMed
  • 8 Bryceson YT, Chiang SC. C, Darmanin S, Fauriat C, Schlums H, Theorell J, Wood SM. J. Innate Immun. 2011; 3: 216
    CrossrefPubMed
  • 9 Silva L. Molecules 2006; 11: 421
    CrossrefPubMed
  • 10 Silva LF. Jr, Carneiro VM. T. Synthesis 2010; 1059
    Article in Thieme Connect
  • 11 Ferraz HM. C, Silva LF. Jr, Vieira Tde O. Synthesis 1999; 2001
    Article in Thieme Connect
  • 12 Hudlicky T, Price JD. Chem. Rev. 1989; 89: 1467
    Crossref
  • 13 Song Z.-L, Fan C.-A, Tu Y.-Q. Chem. Rev. 2011; 111: 7523
    CrossrefPubMed
  • 14 Ferraz HM. C, Carneiro VM. T, Silva LF. Jr. Synthesis 2009; 385
  • 15 Ferraz HM. C, Silva LF. Jr, Vieira TO. Tetrahedron 2001; 57: 1709
    Crossref
  • 16 Cvjetko P, Cvjetko I, Pavlica M. Arhiv za higijenu rada i toksikologiju 2010; 61: 111
    CrossrefPubMed
  • 17 Afshari R, Mégarbane B, Zavar A. Clin. Toxicol. 2012; 50: 791
    CrossrefPubMed
  • 18 Heinen F, Engelage E, Dreger A, Weiss R, Huber SM. Angew. Chem. Int. Ed. 2018; 57: 3830
    CrossrefPubMed
  • 19 Heinen F, Engelage E, Cramer CJ, Huber SM. J. Am. Chem. Soc. 2020; 142: 8633
    CrossrefPubMed
  • 20 Yang H, Wong MW. Molecules 2020; 25: 1045
    CrossrefPubMed
  • 21 Dohi T, Kita Y. Chem. Commun. 2009; 2073
    CrossrefPubMed
  • 22 Khan A, Silva LF. Jr, Rabnawaz M. Asian J. Org. Chem. 2021; 10: 2549
    Crossref
  • 23 Lussari N, Khan A, Pilli RA, Dos Santos AA, Silva LF. Jr, Braga AA. C. New J. Chem. 2022; 46: 20817
    Crossref
  • 24 Ferraz HM. C, Aguilar AM, Silva LF. Jr. Tetrahedron 2003; 59: 5817
    Crossref
  • 25 Silva LF. Jr, Siqueira FA, Pedrozo EC, Vieira FY. M, Doriguetto AC. Org. Lett. 2007; 9: 1433
    CrossrefPubMed
  • 26 Ferraz HM. C, Aguilar AM, Silva LF. Jr. Synthesis 2003; 1031
    Article in Thieme Connect
  • 27 Miyamoto K, Sei Y, Yamaguchi K, Ochiai M. J. Am. Chem. Soc. 2009; 131: 1382
    CrossrefPubMed
  • 28 Ochiai M, Yoshimura A, Miyamoto K. Tetrahedron Lett. 2009; 50: 4792
    Crossref
  • 29 Liu K, Studer A. J. Am. Chem. Soc. 2021; 143: 4903
    CrossrefPubMed
  • 30 Khan A, Sarwar MG, Ali S. Molecules 2024; 29: 501
    CrossrefPubMed