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[1] [2] Pyrroles are found in a variety of natural products with biological activity, so the synthesis of substituted pyrroles has important applications in medicinal chemistry. [3] [4] Alternative methods for synthesizing pyrroles exist, such as the Knorr Pyrrole Synthesis and Paal-Knorr Synthesis. The Hantzsch pyrrole synthesis
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. Small amounts of the N-vinyl product were also observed as well as O-vinylketoxime. The N-vinyl product was then used in the synthesis of a new BODIPY. [5]
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
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
He performed the porphin synthesis at a temperature of 90-95 °C and high pressure in sealed pyrex glass tubes, by reacting pyrrole, 2 % formaldehyde and pyridine in methanol for 30 hours. [7] A simplified version of Rothemund porphyrin synthesis was described by Alan D. Adler and Frederick R. Longo in 1966.
In organic chemistry, the Paal–Knorr synthesis is a reaction used to synthesize substituted furans, pyrroles, or thiophenes from 1,4-diketones.It is a synthetically valuable method for obtaining substituted furans and pyrroles, which are common structural components of many natural products.
An example of the Chan–Lam coupling to synthesize biologically active compounds is shown below: Reaction example of Chan–Lam coupling. Compound 1, a pyrrole, is coupled with aryl boronic acid, 2, to afford product 3, which is then carried forward to the target 4. The nitrile group of 2 does not poison the catalyst.
The Barton–Zard reaction is a route to pyrrole derivatives via the reaction of a nitroalkene with an α-isocyanide under basic conditions. [1] It is named after Derek Barton and Samir Zard who first reported it in 1985.