Topic > Heterocyclic chemistry: the Knorr synthesis of pyrroles

The Knorr synthesis of pyrrole, 2,4-diethoxycarbonyl-3,5-dimethylpyrrole, was obtained by using an α-amino ketone, ethyl acetoaminoacetate, and reacting it with the its predecessor, ethyl acetoacetate in a double condensation reaction. The product was analyzed by 1H NMR, 13C NMR, mass spectrometry and IR spectroscopy giving positive results. Introduction Pyrrole has been a molecule of great interest due to its heterocyclic aromatic properties. The lone pair on nitrogen is delocalized within the ring, making the heterocycle electron-rich. This causes the ring to become increasingly nucleophilic and therefore makes it susceptible to attack by electrophiles. The addition of these new substitutions makes the molecules more important, which make a huge contribution not only to the chemical industry, but also to the biological industry. 1 Substituted pyrrole molecules are fantastic precursors for producing complex molecules, such as medicines, agricultural chemicals, and dyes. Indole, an important benzopyrrole, is the basis of the important protein tryptophan and serves as a neurotransmitter in the brain. The neurotransmitter, serotonin, is important in the production of modern drugs such as sumatriptan which treats migraines.2 The synthesis of pyrrole can be achieved by a large number of methods. Some of the most common processes used in today's laboratory include the Hantzch pyrrole method, the Paal-Knoor Knorr synthesis, and the Knoorr synthesis; the latter which will be studied in this experiment. Other complex methods explored include Robinson's use of the reaction between an aldehyde and a hydrazine. However, this method requires high temperatures which are not economically favorable to maintain and therefore the other classical methods are gene...... half of the article ...... essential of the reaction and products. References Works Cited1. V. Amarnath, DC Anthony, K. Amarnath, WM Valentine, LA Wetterau, DGJ Org. Chemistry. 1991, 56, p. 6924-6931.2. J. Clayden, N. Greeves, S. Warren, P. Wothers. Organic Chemistry. 8th ed. 2007, Oxford University Press, p. 1186-1191.3. GM Robinson, R. Robinson. J. Chem. Soc. 1918, p. 639-645.4. AH Corwin. Heterocyclic compounds. 1950, 1, p. 287.5. Y. Byun, District Attorney Lightner. J. Heterocyclic chemistry. 1991, 28, p. 1683-1692.6. Professor Chris Willis, School of Chemistry, University of Bristol7. Professor Kevin Booker-Milburn, 2nd Year Heterocyclic Notes, School of Chemistry, University of Bristol8. H. Fischer. Organic Syntheses Coll. 1943, 2, p. 202; H. Fischer. Organic Syntheses Coll. 1935, 15, p. 17.9. C. Schmuck, D. Rupprecht. Summary 2007, 2007, 20, pag. 3095-3110.