Metal‐Free Cyclization of  ortho ‐Nitroaryl Ynamides and Ynamines towards Spiropseudoindoxyls | Zendy

Marien Niels | Zendy; Reddy B. Narendraprasad | Zendy; De Vleeschouwer Freija | Zendy; Goderis Steven | Zendy; Van Hecke Kristof | Zendy; Verniest Guido | Zendy

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Metal‐Free Cyclization of ortho ‐Nitroaryl Ynamides and Ynamines towards Spiropseudoindoxyls

Author(s) -

Marien Niels,

Reddy B. Narendraprasad,

De Vleeschouwer Freija,

Goderis Steven,

Van Hecke Kristof,

Verniest Guido

Publication year - 2018

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201800340

Subject(s) - intramolecular force , chemistry , cycloaddition , carbene , ring (chemistry) , nitro , metal , molecule , medicinal chemistry , computational chemistry , photochemistry , stereochemistry , organic chemistry , catalysis , alkyl

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.

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