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Amino Azaxylylenes Photogenerated from o ‐Amido Imines: Photoassisted Access to Complex Spiro‐Poly‐Heterocycles
Author(s) -
Mukhina Olga A.,
Kuznetsov Dmitry M.,
Cowger Teresa M.,
Kutateladze Andrei G.
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201504455
Subject(s) - moiety , chemistry , intramolecular force , yield (engineering) , cycloaddition , molecule , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , materials science , metallurgy
Upon irradiation, cyclic imines containing o ‐amido groups are shown to produce reactive intermediates, amino azaxylylenes, which undergo intramolecular cycloadditions to tethered unsaturated pendants to yield complex N,O‐heterocycles having an additional spiro‐connected nitrogen heterocyclic moiety. Modular assembly of the photoprecursors allows expeditious increase of the complexity of the target poly‐heterocyclic scaffolds with a minimal number of experimentally simple reaction steps. The photocyclization and subsequent postphotochemical transformations are accompanied by an increase of Lovering's fsp3 factor, thus producing unprecedented three‐dimensional molecular architectures, and offering extended sampling of chemical space.