Physical and Theoretical Aspects, Synthesis, and Chemical Reactivity of 2
            <i>H</i>
            ‐ and 3
            <i>H</i>
            ‐Pyrroles

An expedient synthesis of hitherto unknown pyrrolo[2,1a]isoquinolinium salts from non-aromatic aryl-substituted 2Hand 3H-pyrroles and internal alkynes has been developed. The process represents a rare example of N-nucleophilic reaction of 2H-and 3H-pyrroles and relies on the ortho-CÀ H bond activation of non-aromatic arylpyrroles in the presence of rhodium catalyst followed by alkyne annulation reaction. A broad range of diversely substituted salts was obtained in high yields under mild reaction conditions. The photophysical properties for selected representatives of novel pyrrolo[2,1a]isoquinolinium salts have been evaluated to demonstrate their potential as fluorescent materials for light-emitting devices and bioimaging.

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Reaction of (het)aryl cyclohexyl ketoximes with acetylene in the two-phase KOH/DMSO/n-hexane system: en route to spirocyclic 3H-pyrroles

Shabalin

Dvorko

Schmidt

et al. 2015

Mendeleev Communications

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Physical and Theoretical Aspects, Synthesis, and Chemical Reactivity of 2 H ‐ and 3 H ‐Pyrroles

Cited by 12 publications

References 299 publications

Non‐Aromatic 3H‐Pyrroles in the Reaction with Nucleophiles: Is High Reactivity a Myth?

Non‐Aromatic 3H‐Pyrroles in the Reaction with Nucleophiles: Is High Reactivity a Myth?

Unveiling the N‐Nucleophilicity of Non‐Aromatic Pyrroles Through Rhodium Catalysis: A Case of Synthesis and Luminescence Studies of Pyrrolo[2,1‐a]isoquinolinium Salts

Reaction of (het)aryl cyclohexyl ketoximes with acetylene in the two-phase KOH/DMSO/n-hexane system: en route to spirocyclic 3H-pyrroles

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