Title
Synthesis of indoles, benzofurans, and related heterocycles via an acetylene-activated SNAr/intramolecular cyclization cascade sequence in water or DMSO
Department
Natural Sciences
Document Type
Article
Publication Source
Organic and Biomolecular Chemistry
Publication Date
2015-01-01
Volume
13
Issue
8
First Page
2273
Last Page
2284
Abstract
© The Royal Society of Chemistry 2015. The synthesis of 2-substituted indoles and benzofurans was achieved by nucleophilic aromatic substitution, followed by subsequent 5-endo-dig cyclization between the nucleophile and an ortho acetylene. The acetylene serves the dual role of the electron withdrawing group to activate the substrate for SNAr, and the C1-C2 carbon scaffold for the newly formed 5-membered heteroaromatic ring. This method allows for the bond forming sequence of Ar-X-N/O-C1 to proceed in a single synthetic step, furnishing indoles and benzofurans in moderate to high yields. Since the method is not transition metal mediated, brominated and chlorinated substrates are tolerated, and benzofuran formation can be conducted using water or water-DMSO mixtures as solvent. This journal is
DOI
10.1039/c4ob02549k
Recommended Citation
Hudson, R.; Bizier, N. P.; Esdale, K. N.; and Katz, J. L., "Synthesis of indoles, benzofurans, and related heterocycles via an acetylene-activated SNAr/intramolecular cyclization cascade sequence in water or DMSO" (2015). Articles & Book Chapters. 250.
https://digitalcommons.daemen.edu/faculty_scholar/250
https://doi.org/10.1039/c4ob02549k