This site needs JavaScript to work properly. Please enable it to take advantage of the complete set of features!

Skip to main page content

Add to Collections

Your saved search

Name of saved search:

Search terms:

Test search terms

Would you like email updates of new search results?

Yes
No

Email: (change)

Frequency:

Which day?

Which day?

Report format:

Send at most:

Send even when there aren't any new results

Optional text in email:

Your RSS Feed

Review

. 2009 Nov 25;14(12):4814-37.

doi: 10.3390/molecules14124814.

Molecular iodine-mediated cyclization of tethered heteroatom-containing alkenyl or alkynyl systems

Malose Jack Mphahlele¹

Affiliations

Affiliation

¹ Department of Chemistry, College of Science, Engineering and Technology, University of South Africa, P.O. Box 392, Pretoria 0003, South Africa. mphahmj@unisa.ac.za

PMID: 20032861
PMCID: PMC6255281
DOI: 10.3390/molecules14124814

Review

Molecular iodine-mediated cyclization of tethered heteroatom-containing alkenyl or alkynyl systems

Malose Jack Mphahlele. Molecules. 2009.

. 2009 Nov 25;14(12):4814-37.

doi: 10.3390/molecules14124814.

Author

Malose Jack Mphahlele¹

Affiliation

¹ Department of Chemistry, College of Science, Engineering and Technology, University of South Africa, P.O. Box 392, Pretoria 0003, South Africa. mphahmj@unisa.ac.za

PMID: 20032861
PMCID: PMC6255281
DOI: 10.3390/molecules14124814

Abstract

Molecular iodine has established itself as a readily available and easy-to-handle electrophilic and oxidizing reagent used in various organic transformations. In this review attention is focused on the use of molecular iodine in promoting cyclization (iodocyclization and cyclodehydroiodination) of tethered heteroatom-containing alkenyl or alkynyl systems.

PubMed Disclaimer

Figures

Figure 1
Structures of naphtha[2,3-b]furan-4,9-diones 1 and naphtha[1,2-b]furan-4,5-diones 2.

Figure 2
Structures of benzo[b]thiophene analogues 3a–c.

Scheme 1 — Scheme 1
Iodocyclization of 5-penten-1-ol in the presence of pyridine.

Scheme 2 — Scheme 2
Iodocyclization of furyl-substituted pent-4-ene-1,2-diols.

Scheme 3 — Scheme 3
Iodocyclization of alkenyl 1,3-diols.

Scheme 4 — Scheme 4
Base-promoted iodocyclization of α-alkenyl-α-amino esters.

Scheme 5 — Scheme 5
Base-promoted iodocyclization of N-ethoxycarbonyl allylcarbamate.

Scheme 6 — Scheme 6
Iodine-mediated cyclization of N-ethoxycarbonyl N’-allylurea.

Scheme 7 — Scheme 7
Iodine-promoted cyclization of nonconjugated unsaturated acids.

Scheme 8 — Scheme 8
Iodocyclization of (E)-(pyridin-2-yl)allyl acetates.

Scheme 9 — Scheme 9
Iodocyclization of the trichloroacetimidate derivatives of primary α-allenic alcohol.

Scheme 10 — Scheme 10
Iodocyclization of 3-alkyne-1,2-diols.

Scheme 11 — Scheme 11
Iodocyclization of homopropargylic sulfonamides.

Scheme 12 — Scheme 12
Iodocyclization of (E)-(pyridin-2-yl)alkynyl acetates.

Scheme 13 — Scheme 13
Iodocyclization of 2-pyridin-2-yl-pent-4-ynoic acid ethyl esters.

Scheme 14 — Scheme 14
Iodine-promoted cyclization of 2-alkynylanilines, N-tosyl-2-alkynylanilines and 2-(N-tosyl)-3-alkynylpyridine derivatives.

Scheme 15 — Scheme 15
Iodine-promoted cyclization of 2-alkynylanisoles and alkyl(2-alkynylphenyl) sulfides.

Scheme 16 — Scheme 16
Iodine-CAN mediated cyclizations of (2-methoxyaryl) alk-2-yn-1-ones.

Scheme 17 — Scheme 17
Iodine-mediated cyclization of 2-(N,N-dimethylaminophenyl)alk-2-yn-1-ones.

Scheme 18 — Scheme 18
Iodine-mediated cyclization of 2-(N,N-dimethylamino) substituted ynones.

Scheme 19 — Scheme 19
Iodine-mediated cyclization of 2-(N,N-dimethylaminophenyl)alk-2-yn-1-ols in polar aprotic (CH₃CN) and polar protic (methanol or ethanol) solvents.

Scheme 20 — Scheme 20
Iodine-NaHCO₃ promoted cyclization of β-(2-aminophenyl)-α,β-ynone.

Scheme 21 — Scheme 21
Iodine-K₂CO₃ mediated cylization of o-(1-alkynyl)benzenesulfonamides.

Scheme 22 — Scheme 22
Iodine-NaHCO₃ mediated cylization of o-(1-alkynyl)benzamides.

Scheme 23 — Scheme 23
Iodine-SnCl₄ mediated cylization of 2-allylphenol.

Scheme 24 — Scheme 24
Iodine-SnCl₄ mediated cylization of 2-(2-butenyl)phenol.

Scheme 25 — Scheme 25
I₂–NaHCO₃ mediated iodoenolcyclization of 2-alkenyl-1,3-dicarbonyl compounds.

Scheme 26 — Scheme 26
I₂–Na₂CO₃ mediated iodoenolcyclization of 2-allyl-1,3-dicarbonyl derivatives.

Scheme 27 — Scheme 27
Iodine-mediated cylization of 2-allylcyclohexane-1,3-diones.

Scheme 28 — Scheme 28
Iodocyclization of 2-allyl-3-benzylamino-5,5-dimethyl-2-cyclohexen-1-one.

Scheme 29 — Scheme 29
Iodine-methanol promoted cyclization of 2-allyl-3-benzylamine-2-cyclohexen-1-ones.

Scheme 30 — Scheme 30
Iodocyclization of β-keto sulfones and subsequent dehydroiodination.

Scheme 31 — Scheme 31
Iodine-mediated carbocyclization of active methylene compounds.

Scheme 32 — Scheme 32
One-pot iodocyclization and oxidative dehydrogenation of 2-hydroxy-3-phenylprop-2-en-1-ones.

Scheme 33 — Scheme 33
Iodine-mediated oxidative desulfurization promoted cyclization of thioamides.

Scheme 34 — Scheme 34
One-pot iodocyclization and oxidative aromatization of 2-allylcyclohexenones.

Scheme 35 — Scheme 35
Iodocyclization and oxidative aromatization of diethyl {[2-(2-propenyl)cyclohexenone]methyl}phosphonates.

See this image and copyright information in PMC

Similar articles

Iodine-mediated solvent-controlled selective electrophilic cyclization and oxidative esterification of o-alkynyl aldehydes: an easy access to pyranoquinolines, pyranoquinolinones, and isocumarins.
Verma AK, Rustagi V, Aggarwal T, Singh AP. Verma AK, et al. J Org Chem. 2010 Nov 19;75(22):7691-703. doi: 10.1021/jo101526b. Epub 2010 Oct 29. J Org Chem. 2010. PMID: 21033701
A simple and mild synthesis of 1H-isochromenes and (Z)-1-alkylidene-1,3-dihydroisobenzofurans by the iodocyclization of 2-(1-alkynyl)benzylic alcohols.
Mancuso R, Mehta S, Gabriele B, Salerno G, Jenks WS, Larock RC. Mancuso R, et al. J Org Chem. 2010 Feb 5;75(3):897-901. doi: 10.1021/jo902333y. J Org Chem. 2010. PMID: 20043652 Free PMC article.
Synthesis of dibenzocyclohepten-5-ones by electrophilic iodocyclization of 1-([1,1'-biphenyl]-2-yl)alkynones.
Chen Y, Huang C, Liu X, Perl E, Chen Z, Namgung J, Subramaniam G, Zhang G, Hersh WH. Chen Y, et al. J Org Chem. 2014 Apr 18;79(8):3452-64. doi: 10.1021/jo5001803. Epub 2014 Mar 31. J Org Chem. 2014. PMID: 24641681
[Novel iodocyclization method based on the controlling of oxidative aromatization].
Okitsu T. Okitsu T. Yakugaku Zasshi. 2011;131(9):1323-7. doi: 10.1248/yakushi.131.1323. Yakugaku Zasshi. 2011. PMID: 21881306 Review. Japanese.
Iodine-mediated synthesis of heterocycles via electrophilic cyclization of alkynes.
Aggarwal T, Kumar S, Verma AK. Aggarwal T, et al. Org Biomol Chem. 2016 Aug 10;14(32):7639-53. doi: 10.1039/c6ob01054g. Org Biomol Chem. 2016. PMID: 27383580 Review.

See all similar articles

Cited by

Recent advances in the synthesis of thiophene derivatives by cyclization of functionalized alkynes.
Mancuso R, Gabriele B. Mancuso R, et al. Molecules. 2014 Sep 29;19(10):15687-719. doi: 10.3390/molecules191015687. Molecules. 2014. PMID: 25268722 Free PMC article. Review.
Molecular iodine--an expedient reagent for oxidative aromatization reactions of alpha,beta-unsaturated cyclic compounds.
Mphahlele MJ. Mphahlele MJ. Molecules. 2009 Dec 16;14(12):5308-22. doi: 10.3390/molecules14125308. Molecules. 2009. PMID: 20032894 Free PMC article. Review.
Recent progress in transition-metal-free functionalization of allenamides.
Li X, Liu Y, Ding N, Tan X, Zhao Z. Li X, et al. RSC Adv. 2020 Oct 6;10(60):36818-36827. doi: 10.1039/d0ra07119f. eCollection 2020 Oct 1. RSC Adv. 2020. PMID: 35517974 Free PMC article. Review.
Preparation and Utility of N-Alkynyl Azoles in Synthesis.
Reinus B, Kerwin SM. Reinus B, et al. Molecules. 2019 Jan 24;24(3):422. doi: 10.3390/molecules24030422. Molecules. 2019. PMID: 30682796 Free PMC article. Review.
Iodine-catalyzed efficient synthesis of xanthene/thioxanthene-indole derivatives under mild conditions.
Miao W, Ye P, Bai M, Yang Z, Duan S, Duan H, Wang X. Miao W, et al. RSC Adv. 2020 Jul 2;10(42):25165-25169. doi: 10.1039/d0ra05217e. eCollection 2020 Jun 29. RSC Adv. 2020. PMID: 35517437 Free PMC article.

See all "Cited by" articles

References

1. El-Tach G.M.M., Evans A.B., Knight D.W., Jones S. Practical alternatives for the synthesis of β-iodofurans by 5-endo-dig cyclizations of 3-alkyne-1,2-diols. Tetrahedron Lett. 2001;42:5945–5948.
1. Sniady A.A., Wheeler K.A., Dembismski R. 5-Endo-dig electrophilic cyclization of 1,4-disubstituted but-3-yn-1-ones: Regiocontrolled synthesis of 2,5-disubstituted 3-bromo- and 3-iodofurans. Org. Lett. 2005;7:1769–1772. doi: 10.1021/ol050372i. - DOI - PubMed
1. Bew S.P., Knight D.W. A brief synthesis of β-iodofurans. J. Chem. Soc. Chem. Commun. 1996:1007–1008. doi: 10.1039/CC9960001007. - DOI
1. Knight D.W., Redfern A.L., Gilmore J. The synthesis of 5-substituted proline derivatives and of 5-substituted pyrrole-2-carboxylates by 5-endo cyclisations featuring a method for effectively favouring these with respect to 5-exo cyclisations. J. Chem. Soc. Perkin Trans. I. 2001:2874–2883. doi: 10.1039/b106739g. - DOI
1. Knight D.W., Redfern A.L., Gilmore J. An approach to 2,3-dihydropyrroles and β-iodopyrroles based on 5-endo-dig cyclizations. J. Chem. Soc. Perkin Trans. I. 2002:622–628. doi: 10.1039/b110751h. - DOI

Publication types

Actions
Actions

MeSH terms

Actions
Actions
Actions

Substances

Actions

LinkOut - more resources

Full Text Sources