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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). This is followed by the loss of H 2 O, giving an imine (5).
2,5-Bis(hydroxymethyl)pyrrole is an organic chemical compound with formula C 6 H 9 O 2 N, or (HOCH 2) 2 (C 4 H 3 N). Its molecule can be described as that of pyrrole C 4 H 5 N with hydroxymethyl groups HO−CH 2 − replacing the two hydrogen atoms adjacent to the nitrogen atom. The compound is a white solid, soluble in water and acetone.
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 p K a of +3.7.
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.
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
Pyrrole Ring. The Paal–Knorr reaction is quite versatile. In all syntheses almost all dicarbonyls can be converted to their corresponding heterocycle. R2 and R5 can be H, aryl or alkyl. R3 and R4 can be H, aryl, alkyl, or an ester. In the pyrrole synthesis (X = N), R1 can be H, aryl, alkyl, amino, or hydroxyl. [9]
Only one regioisomer was observed. In this case, the reaction conditions were sufficient to form the N-vinyl pyrrole [4] 2-mesityl-3-methylpyrrole was synthesized in 2004 via the Trofimov reaction. The reaction of the ketoxime with acetylene yielded a mixture of products with the primary one being the N-H pyrrole.
Tetrapyrroles are a class of chemical compounds that contain four pyrrole or pyrrole-like rings. The pyrrole/pyrrole derivatives are linked by (= (CH)-or -CH 2-units), in either a linear or a cyclic fashion. Pyrroles are a five-atom ring with four carbon atoms and one nitrogen atom.