Amino Azaxylylenes Photogenerated from o-Amido Imines: Photoassisted Access to Complex Spiro-Poly-Heterocycles

Authors

Olga A. Mukhina, University of Denver
Dmitry Kuznetsov, University of Denver
Teresa M. Cowger, University of DenverFollow
Andrei G. Kutateladze, University of DenverFollow

Publication Date

6-30-2015

Document Type

Article

Organizational Units

College of Natual Science and Mathematics, Chemistry and Biochemistry

Keywords

Cycloaddition, Heterocyclic

Abstract

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.

Publication Statement

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Recommended Citation

Mukhina, O. A., Kuznetsov, D. M., Cowger, T. M., & Kutateladze, A. G. (2015). Amino Azaxylylenes Photogenerated from o‐Amido Imines: Photoassisted Access to Complex Spiro‐Poly‐Heterocycles. Angewandte Chemie, 127(39), 11678-11682. DOI: 10.1002/anie.201504455.