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A library of substituted pyrrole analogs can be quickly produced by using continuous flow chemistry (reaction times of around 8 min.). [10] The advantage of using this method, as opposed to the in-flask synthesis, is that this one does not require the work-up and purification of several intermediates, and could therefore lead to a higher ...
The amine attacks the other carbonyl to form a 2,5-dihydroxytetrahydropyrrole derivative which undergoes dehydration to give the corresponding substituted pyrrole. [7] Paal–Knorr pyrrole synthesis mechanism. The reaction is typically run under protic or Lewis acidic conditions, with a primary amine.
Pyrrole is an extremely weak base for an amine, with a conjugate acid pK a of −3.8. The most thermodynamically stable pyrrolium cation (C 4 H 6 N +) is formed by protonation at the 2 position. Substitution of pyrrole with alkyl substituents provides a more basic molecule—for example, tetramethylpyrrole has a conjugate acid pK a of +3.7.
The Knorr pyrrole synthesis is a widely used chemical reaction that synthesizes substituted pyrroles (3). [1] [2] [3] The method involves the reaction of an α-amino-ketone (1) and a compound containing an electron-withdrawing group (e.g. an ester as shown) α to a carbonyl group (2). [4] The Knorr pyrrole synthesis
The condensation reaction can be shown below: After the condensation, the pyrrole formation can proceed as normal. The Trofimov reaction can produce both N-H and N-vinyl pyrroles depending on the reaction conditions used. The N-vinyl pyrrole can be formed by the deprotonation of the pyrrole nitrogen which then attacks a second acetylene molecule.
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Hofmann Isonitrile synthesis, Carbylamine reaction; Hofmann product; Hofmann rearrangement; Hofmann–Löffler reaction, Löffler–Freytag reaction, Hofmann–Löffler–Freytag reaction; Hofmann–Martius rearrangement; Hofmann's rule; Hofmann–Sand reaction; Homo rearrangement of steroids; Hooker reaction; Horner–Wadsworth–Emmons ...
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