Metal-Free Cyclization of ortho-Nitroaryl Ynamides and Ynamines towards Spiropseudoindoxyls.

Authors :: Marien N
Reddy BN
De Vleeschouwer F
Goderis S
Van Hecke K
Verniest G
Source :: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2018 May 14; Vol. 57 (20), pp. 5660-5664. Date of Electronic Publication: 2018 Apr 16.
Publication Year :: 2018
Abstract: An efficient metal-free cascade reaction between 1-dibromovinyl-2-nitro-substituted arenes and secondary amines results in the formation of polycyclic pseudoindoxyls in a single step. The reaction mechanism leading to these fused ring systems was investigated, and is believed to involve the initial formation of nitroarylated ynamines/ynamides. These intermediates cycloisomerize towards N-alkenyl-tethered 2-aminoisatogens via a carbene intermediate as demonstrated by QTAIM (quantum theory of atoms in molecules) and ELF (electron localization function) analysis. A subsequent intramolecular dipolar cycloaddition afforded the title compounds.<br /> (© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)

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