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The Knorr pyrrole synthesis involves the reaction of an α-amino ketone or an α-amino-β-ketoester with an activated methylene compound. [15] [16] [17] The method involves the reaction of an α-amino ketone (1) and a compound containing a methylene group α to (bonded to the next carbon to) a carbonyl group (2). [18] The Knorr pyrrole synthesis
Below is one published mechanism for the reaction: [5] Mechanism for the Hantzsch Pyrrole Synthesis. The mechanism starts with the amine (1) attacking the β carbon of the β-ketoesters (2), and eventually forming an enamine (3). The enamine then attacks the carbonyl carbon of the α-haloketone (4).
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.
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
A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). [1] Heterocyclic organic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and applications of organic heterocycles. [2]
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.
Pyrrolines, also known under the name dihydropyrroles, are three different heterocyclic organic chemical compounds that differ in the position of the double bond.Pyrrolines are formally derived from the aromate pyrrole by hydrogenation. 1-Pyrroline is a cyclic imine, whereas 2-pyrroline and 3-pyrroline are cyclic amines.
[1] [2] Simple aromatic rings can be heterocyclic if they contain non-carbon ring atoms, for example, oxygen, nitrogen, or sulfur. They can be monocyclic as in benzene, bicyclic as in naphthalene, or polycyclic as in anthracene. Simple monocyclic aromatic rings are usually five-membered rings like pyrrole or six-membered rings like pyridine.