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Issue 23, 2018
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Expedient synthesis of 3-hydroxypyrroles via Bu3SnH-triggered ionic 5-exo-trig-cyclization of 5-chloro-3-azamuconoate derivatives

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Abstract

An unprecedented application of tributyltin hydride (TBTH) as a reagent for the reductive ionic 1,5-cyclization of 3-azamuconoates (3-azahexa-2,4-dienedioates) is described. A novel 1,5-exo-trig-cyclization of 5-chloro-3-azamuconoates was used as a base for the development of an effective two-step method for the preparation of 4-hydroxy-1H-pyrrole-3-carboxylic and 3-hydroxy-1H-pyrrole-2,4-dicarboxylic acids derivatives from readily available diazo esters and 2-chloro-2H-azirines or 4-chloroisoxazoles. The experimental results, as well as the DFT calculations of the pyrroles formation, are in good agreement with the ionic mechanism involving the initial hydride attack at the C[double bond, length as m-dash]N bond of the azamuconoate followed by tin-promoted 1,5-cyclization.

Graphical abstract: Expedient synthesis of 3-hydroxypyrroles via Bu3SnH-triggered ionic 5-exo-trig-cyclization of 5-chloro-3-azamuconoate derivatives

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Publication details

The article was received on 09 Sep 2018, accepted on 15 Oct 2018 and first published on 16 Oct 2018


Article type: Research Article
DOI: 10.1039/C8QO00982A
Citation: Org. Chem. Front., 2018,5, 3396-3401
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    Expedient synthesis of 3-hydroxypyrroles via Bu3SnH-triggered ionic 5-exo-trig-cyclization of 5-chloro-3-azamuconoate derivatives

    A. V. Agafonova, I. A. Smetanin, N. V. Rostovskii, A. F. Khlebnikov and M. S. Novikov, Org. Chem. Front., 2018, 5, 3396
    DOI: 10.1039/C8QO00982A

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