Synthesis and reactions of new 2-hydroxymethyldimethoxyindoles. Issue 1 (7th January 2016)

• Record Type: Journal Article
• Authors: Bingul, Murat; Kumar, Naresh; Black, David StC.
• Is Part Of: Tetrahedron. Volume 72:Issue 1(2016)
• Page Start: 234
• Page End: 239
• Publication Date: 2016-01-07
• Subjects: 2-Hydroxydimethoxyindoles -- Reduction -- Oxidation -- Indolo-cyclotriveratrylene -- 2-Nitrovinylindole; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2015.11.038
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Lithium aluminium hyride was used as a reducing agent to prepare a range of 2-hydroxymethyldimethoxyindole derivatives from the related methyl esters. Acid-catalysed reactions of these indole-2-methanols yielded indolo-cyclotriveratrylenes linked through C-2 and C-3. The related indole-2-carbaldehydes were prepared via oxidation of the indole-2-methanols in the presence of manganese dioxide. Vilsmeier formylation was explored to prepare new formylated indole-2-carbaldehydes. Furthermore, the treatment of indole-2-carbaldehydes with nitromethane led to the formation of 2-nitrovinylindoles. Graphical abstract: