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A new and high yielding synthesis of unstable pyrroles via a modified Clauson-Kaas reaction.
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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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.
|Keywords:||Pyrrole Synthesis Clauson-Kaas pyrrolic dimethoxytetrahydrofuran Paul-Knorr|
|Journal or Publication Title:||Tetrahedron Letters|
|Page Range:||pp. 799-801|
|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|
|Item Statistics:||View statistics for this item|
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