Iodine-induced reaction cascades for the rapid construction of variously substituted benzothiophenes
- PMID: 14602004
- DOI: 10.1021/ol035663a
Iodine-induced reaction cascades for the rapid construction of variously substituted benzothiophenes
Abstract
[reaction: see text] Readily accessible propynols with a 2-thioxyphenyl substituent selectively undergo 5-exo-iodocyclization followed by tandem rearrangement and elimination or substitution processes to give selective access to either 2-acyl- or 2-(1-iodoalkeny)-benzo[b]thiophene systems.
Similar articles
-
Isonitrile trapping reactions under thermolysis of alkoxyamines for the synthesis of quinolines.Org Lett. 2006 Apr 27;8(9):1875-8. doi: 10.1021/ol0604421. Org Lett. 2006. PMID: 16623573
-
Selective endo and exo iodocyclizations in the synthesis of quinolines and indoles.Org Lett. 2006 Jan 19;8(2):243-6. doi: 10.1021/ol052518j. Org Lett. 2006. PMID: 16408885
-
A synthetic entry to furo[2,3-b]pyridin-4(1H)-ones and related furoquinolinones via iodocyclization.Org Lett. 2006 Mar 16;8(6):1113-6. doi: 10.1021/ol053048w. Org Lett. 2006. PMID: 16524281
-
Iodocyclization of ethoxyethyl ethers to alkynes: a broadly applicable synthesis of 3-iodobenzo[b]furans.Org Lett. 2008 Nov 6;10(21):4967-70. doi: 10.1021/ol8020463. Epub 2008 Oct 3. Org Lett. 2008. PMID: 18831555
-
Electrophilic substitution of deep cavity cavitands: selective exo functionalization of molecular concavity.Org Lett. 2007 Mar 1;9(5):745-8. doi: 10.1021/ol062897w. Epub 2007 Feb 6. Org Lett. 2007. PMID: 17279760
Cited by
-
Synthesis of 2,3-disubstituted benzo[b]selenophenes via electrophilic cyclization.J Org Chem. 2006 Mar 17;71(6):2307-12. doi: 10.1021/jo0524268. J Org Chem. 2006. PMID: 16526778 Free PMC article.
-
Synthesis of Substituted Quinolines by the Electrophilic Cyclization of N-(2-Alkynyl)anilines.Tetrahedron. 2010 Feb 6;66(6):1177. doi: 10.1016/j.tet.2009.12.012. Tetrahedron. 2010. PMID: 20161633 Free PMC article.
-
Synthesis of 3,4-disubstituted 2H-benzopyrans through C-C bond formation via electrophilic cyclization.J Org Chem. 2007 Feb 16;72(4):1347-53. doi: 10.1021/jo062234s. J Org Chem. 2007. PMID: 17288382 Free PMC article.
-
When gold can do what iodine cannot do: A critical comparison.Beilstein J Org Chem. 2011;7:847-59. doi: 10.3762/bjoc.7.97. Epub 2011 Jun 22. Beilstein J Org Chem. 2011. PMID: 21804881 Free PMC article.
-
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.
LinkOut - more resources
Full Text Sources
Other Literature Sources