Amino Azaxylylenes Photogenerated from <i>o</i>‐Amido Imines: Photoassisted Access to Complex Spiro‐Poly‐Heterocycles

Mukhina, Olga A.; Kuznetsov, Dmitry M.; Cowger, Teresa M.; Kutateladze, Andrei G.

doi:10.1002/anie.201504455

Cited by 56 publications

(29 citation statements)

References 32 publications

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“…2 Dearomatization of electron-rich heterocycles such as indoles, 3 furans, 4 and pyrroles 5 is precedented in the literature, including our own recent contributions. 6,7 …”

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confidence: 99%

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Photoassisted Synthesis of Complex Molecular Architectures: Dearomatization of Benzenoid Arenes with Aza‐o‐xylylenes via an Unprecedented [2+4] Reaction Topology

2016

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A new method for photoinduced dearomatization of arenes via an intramolecular cycloaddition with aza-o-xylylenes generated by the excited-state intramolecular proton transfer (ESIPT) in the readily available photoprecursors is developed. The topology of this cycloaddition, [2+4], is unprecedented for photo-dearomatizations of benzenoid aromatic carbocycles. It provides rapid access to novel heterocycles, cyclohexadieno-oxazolidino-quinolinols, as valuable synthons for a broad range of postphotochemical transformations.

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“…2 Dearomatization of electron-rich heterocycles such as indoles, 3 furans, 4 and pyrroles 5 is precedented in the literature, including our own recent contributions. 6,7 …”

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confidence: 99%

“…6d The reaction is initiated by the electrophilic N-centered radical, with the overall process resembling a formal inverse electron demand Diels-Alder reaction. We hypothesized that a similar initial step should occur with donor-substituted benzenoid arenes.…”

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confidence: 99%

Photoassisted Synthesis of Complex Molecular Architectures: Dearomatization of Benzenoid Arenes with Aza‐o‐xylylenes via an Unprecedented [2+4] Reaction Topology

2016

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“…4 The synthesis of photoprecursors for such cycloadditions is facile and straightforward, and also is congruent with the philosophy of Diversity-Oriented Synthesis. 5 The photoproducts can be successfully engaged in experimentally simple postphotochemical ground state reactions 6 resulting in further growth of complexity and generation of novel molecular architectures.…”

Section: Introductionmentioning

confidence: 62%

Photoassisted access to complex polyheterocycles containing a β-lactam moiety

Umstead

Mukhina

Kutateladze

2016

Journal of Photochemistry and Photobiology A: Chemistry

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Intramolecular cycloadditions of aza-o-xylylenes generated via excited state intramolecular proton transfer (ESIPT) to furanacetic acid-based unsaturated pendants was shown to overcome the unfavorable energetics of the azetidinone ring formation, offering rapid access to β-lactams as primary photoproducts. These 2,3- and 3,4-dihydrofuran-containing reactive intermediates are suitable for a broad spectrum of postphotochemical transformations yielding complex polyheterocyclic molecular architectures possessing the β-lactam moiety.

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“…35 Especially the generation of hetero aza-o-xylylenes (heteroatom analogue o-QDMs) was repeatedly used to enable elegant syntheses of complex structural motifs. [36][37][38][39] To the best of our knowledge, there is only one report that indicates the formation of o-QDMs using visible light: Furukawa…”

Section: -25mentioning

confidence: 99%

Visible Light-Induced Ligation via o-Quinodimethane Thioethers

et al. 2018

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We introduce a photocaged diene system ( o-quinodimethane thioethers) based on o-methylbenzaldehydes ( o-MBAs) that can be activated with visible light. The pioneered system is accessible in a single step from commercially available starting materials in excellent yields. Variable synthetic handles can be attached to the photocaged diene, often without elaborate protecting group chemistry. Full conversion of various o-methylbenzaldehydes to the Diels-Alder adduct is achieved in the presence of maleimides under catalyst-free conditions triggered by visible light irradiation with LEDs under flow conditions. Unlike the previously reported UV-induced ligation of o-quinodimethanes, the reaction can be conducted both in organic solvents and in aqueous solution. We further demonstrate the ability of the photocaged dienes to ligate two polymer blocks by visible light. The [4+2] nature of the reaction makes it a powerful orthogonal ligation platform.

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

Abstract: Graphical abstract

Cited by 56 publications

References 32 publications

Photoassisted Synthesis of Complex Molecular Architectures: Dearomatization of Benzenoid Arenes with Aza‐o‐xylylenes via an Unprecedented [2+4] Reaction Topology

Photoassisted Synthesis of Complex Molecular Architectures: Dearomatization of Benzenoid Arenes with Aza‐o‐xylylenes via an Unprecedented [2+4] Reaction Topology

Photoassisted access to complex polyheterocycles containing a β-lactam moiety

Visible Light-Induced Ligation via o-Quinodimethane Thioethers

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