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Studies towards iodine-catalyzed dehydrative-cycloisomerization of pent-4-yne-1,2-diols to di- and tri-substituted furans.
- Source :
-
Tetrahedron . Oct2018, Vol. 74 Issue 41, p6047-6056. 10p. - Publication Year :
- 2018
-
Abstract
- Abstract An efficient and single-step iodine catalyzed and metal-free synthesis of di and tri-substituted 2-methylfuran derivatives were achieved from 1-popargyl-1,2-diols. Stereospecific synthesis of starting 1,2-diols was achieved by indium mediated Barbier type propargylation on corresponding keto-alcohols or by sodium borohydride mediated reduction of 2-hydroxy-2-propargyl ketones. The furan synthesis proceeded through iodine mediated 5-exo-trig cyclization, dehydration and reductive deiodination. The method was applied to the synthesis of 2-methylfuran fused to phenanthrene, pyrene and acenaphthylene rings. Graphical abstract Image 1 [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00404020
- Volume :
- 74
- Issue :
- 41
- Database :
- Academic Search Index
- Journal :
- Tetrahedron
- Publication Type :
- Academic Journal
- Accession number :
- 131767030
- Full Text :
- https://doi.org/10.1016/j.tet.2018.08.032