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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, A new and high yielding synthesis of unstable pyrroles via a modified Clauson-Kaas reaction, Tetrahedron Letters, 47, (5) pp. 799-801. ISSN 0040-4039 (2006) [Refereed Article]

DOI: doi:10.1016/j.tetlet.2005.11.104


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-dihydroxytetrahydrofuran 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. © 2005 Elsevier Ltd. All rights reserved.

Item Details

Item Type:Refereed Article
Research Division:Chemical Sciences
Research Group:Organic chemistry
Research Field:Organic chemical synthesis
Objective Division:Expanding Knowledge
Objective Group:Expanding knowledge
Objective Field:Expanding knowledge in the chemical sciences
UTAS Author:Gourlay, BS (Dr Brendon Gourlay)
UTAS Author:Molesworth, PP (Dr Peter Molesworth)
UTAS Author:Smith, JA (Associate Professor Jason Smith)
ID Code:43127
Year Published:2006
Web of Science® Times Cited:49
Deposited By:Chemistry
Deposited On:2006-08-01
Last Modified:2009-10-06

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