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Issue 12, 2018
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Synthesis of medium-sized aryl-fused nitrogenous heterocycles via sequential aryne aza-Claisen rearrangement/ring-closing metathesis

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Abstract

The reaction of arynes and secondary allylamines furnished ortho-allyl-substituted N-arylanilines via an aza-Claisen rearrangement. In this transformation, the sequential formation of C–C and C–N bonds occurred by involving two aryne molecules under metal-free reaction conditions to provide moderate to good yields of the products. The obtained ortho-allyl-substituted N-arylaniline derivatives were further converted into aryl-fused medium-sized (7–9) nitrogenous heterocyclic molecules such as azepines, azocines and azonines via ring-closing metathesis (RCM).

Graphical abstract: Synthesis of medium-sized aryl-fused nitrogenous heterocycles via sequential aryne aza-Claisen rearrangement/ring-closing metathesis

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Publication details

The article was received on 22 Dec 2017, accepted on 16 Feb 2018 and first published on 16 Feb 2018


Article type: Paper
DOI: 10.1039/C7OB03166A
Citation: Org. Biomol. Chem., 2018,16, 2134-2142
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    Synthesis of medium-sized aryl-fused nitrogenous heterocycles via sequential aryne aza-Claisen rearrangement/ring-closing metathesis

    N. S. V. M. Rao Mangina, R. Guduru and G. V. Karunakar, Org. Biomol. Chem., 2018, 16, 2134
    DOI: 10.1039/C7OB03166A

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