Electrophile-driven regioselective synthesis of functionalized quinolines
- PMID: 21491872
- DOI: 10.1021/ol2007154
Electrophile-driven regioselective synthesis of functionalized quinolines
Abstract
Highly substituted 3-iodoquinolines bearing different alkyl and aryl moieties can be synthesized in moderate to excellent yields (up to 99%) by 6-endo-dig iodocyclization of 2-tosylaminophenylprop-1-yn-3-ols with molecular iodine (I(2)) under mild conditions. The cyclization is highly regioselective and the resulting 3-iodoquinolines can be further functionalized by various coupling reactions.
Similar articles
-
Synthesis of 5-iodopyrrolo[1,2-a]quinolines and indolo[1,2-a]quinolines via iodine-mediated electrophilic and regioselective 6-endo-dig ring closure.J Org Chem. 2011 Jul 15;76(14):5670-84. doi: 10.1021/jo200638k. Epub 2011 Jun 16. J Org Chem. 2011. PMID: 21619026
-
Regioselective, Molecular Iodine-Mediated C3 Iodination of Quinolines.Org Lett. 2015 Sep 18;17(18):4408-11. doi: 10.1021/acs.orglett.5b01857. Epub 2015 Aug 3. Org Lett. 2015. PMID: 26235562
-
Synthesis of 2,4-diiodoquinolines via the photochemical cyclization of o-alkynylaryl isocyanides with iodine.J Org Chem. 2011 Feb 18;76(4):1163-6. doi: 10.1021/jo1021772. Epub 2011 Jan 18. J Org Chem. 2011. PMID: 21244063
-
Chemistry of polyvalent iodine.Chem Rev. 2008 Dec;108(12):5299-358. doi: 10.1021/cr800332c. Chem Rev. 2008. PMID: 18986207 Free PMC article. Review. No abstract available.
-
Molecular iodine-mediated cyclization of tethered heteroatom-containing alkenyl or alkynyl systems.Molecules. 2009 Nov 25;14(12):4814-37. doi: 10.3390/molecules14124814. Molecules. 2009. PMID: 20032861 Free PMC article. Review.
Cited by
-
Copper-catalyzed tandem annulation/arylation for the synthesis of diindolylmethanes from propargylic alcohols.Chem Commun (Camb). 2014 Oct 21;50(82):12293-6. doi: 10.1039/c4cc05901h. Chem Commun (Camb). 2014. PMID: 25178910 Free PMC article.
-
One-pot phosphine-catalyzed syntheses of quinolines.J Org Chem. 2012 Sep 21;77(18):8257-67. doi: 10.1021/jo3015825. Epub 2012 Sep 6. J Org Chem. 2012. PMID: 22928667 Free PMC article.
-
Iodo-Cycloisomerization of Aryl(indol-3-yl)methane-Tethered Propargyl Alcohols to 3-Iodocarbazoles via Selective 1,2-Alkyl Migration.ACS Omega. 2018 Nov 7;3(11):15024-15034. doi: 10.1021/acsomega.8b02393. eCollection 2018 Nov 30. ACS Omega. 2018. PMID: 31458169 Free PMC article.
-
Green Synthesis of Halogenated Thiophenes, Selenophenes and Benzo[b]selenophenes Using Sodium Halides as a Source of Electrophilic Halogens.Tetrahedron Lett. 2017 Feb 15;58(7):638-641. doi: 10.1016/j.tetlet.2017.01.007. Epub 2017 Jan 7. Tetrahedron Lett. 2017. PMID: 29277842 Free PMC article.
-
Recent advances in metal-free catalysts for the synthesis of N-heterocyclic frameworks focusing on 5- and 6-membered rings: a review.RSC Adv. 2025 Mar 31;15(13):9676-9755. doi: 10.1039/d5ra00962f. eCollection 2025 Mar 28. RSC Adv. 2025. PMID: 40165917 Free PMC article. Review.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
Other Literature Sources