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A new and high yielding synthesis of unstable pyrroles via a modified Clauson-Kaas reaction.

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Gourlay, BS and Molesworth, PP and Ryan, JH and Smith, JA (2006) A new and high yielding synthesis of unstable pyrroles via a modified Clauson-Kaas reaction. Tetrahedron Letters, 47. pp. 799-801. ISSN 0040-4039

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Abstract

An investigation of the reaction requirements to effect the Clauson-Kaas pyrrole synthesis led to the formulation of a new procedure that avoids the contact of pyrroles to heat or strongly acidic conditions that cause decomposition of the desired products. The procedure involves mild hydrolysis of 2,5-dimethoxytetrahydrofuran in water to the activated species 2,5-dihydroxy- tetrahydrofuran that reacts with primary amines in an acetate buffer at room temperature to give N-substituted pyrroles in high yield. In the case of chiral amines, pyrrole formation proceeds with no detectable epimerisation. Acid- or heat-sensitive pyrroles are also obtained in high yield and purity.

Item Type: Article
Keywords: Pyrrole Synthesis Clauson-Kaas pyrrolic dimethoxytetrahydrofuran Paul-Knorr
Journal or Publication Title: Tetrahedron Letters
Page Range: pp. 799-801
ISSN: 0040-4039
Identification Number - DOI: 10.1016/j.tetlet.2005.11.104
Additional Information: The definitive version is available at http://www.sciencedirect.com/
Date Deposited: 18 Mar 2008 02:47
Last Modified: 18 Nov 2014 03:32
URI: http://eprints.utas.edu.au/id/eprint/3564
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