Pyrrole: Synthesis, Reactions, and Medicinal Uses
"Explore the synthesis methods of pyrrole, its electrophilic substitution reactions, acetylation, oxidation, reduction, and various medicinal uses. Pyrrole is a crucial heterocyclic compound found in natural substances like alkaloids, haemoglobin, and chlorophyll. Discover how pyrrole plays a significant role in pharmaceutical chemistry and its diverse applications in medicine." (296 characters)
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Kota.Swathi Assistant Professor Department of Pharmaceutical Chemistry St. Peter s institute of pharmaceutical sciences
Pyrrole is an unsaturated five membered heterocyclic compound with nitrogen as heteroatom at 1stposition. It is a word derived from Greek, which pyrros means fiery oil. Molecular fomula: C H N. One of the important heterocyclic compound because many naturally occuring compounds contain pyrrole ring. E.g: Alkaloids, haemoglobin, chlorophyll . It produces a bright red color when brought in contact with a pine splint moistened with conc. HCl. Source: Occurs in bone oil, coal tar & also derived from proteins. Obtained from dry distillation or pyrrolysis of animal byproducts such as horns, hooves & bones.
Synthesis 1. FROM BONE OIL Bone oil dil. Alkali bone oil free from acidic impurities dil.acid bone oil free from basic impurities fractional distillation Pyrrole ring fraction obtained (373K-423K) fused with KOH Potassium salt of Pyrrole steam distillation Pure Pyrrole (C H N) 2. FROM ACETYLENE (COMMERCIAL METHOD): Pyrrole can be synthesized commercially by passing a mixture of acetylene & ammonia through a red hot tube. HC CH + HC CH NH
3. FROM SUCCINIMIDE: when succinimide is distilled with Zn dust, it reduced to pyrrole. 4. FROM FURAN: Furan on heating with ammonia in the presence of alumina (Al O ) gives pyrrole over 400 C. 5. PAAL-KNORR SYNTHESIS: By heating 1,4-dicarbonyl compounds with ammonia / primary amines/ hydrazines to give pyrrole derivatives is known as paal knorr synthesis.
Electrophilic Substitution Reactions Pyrrole undergoes substitution reaction predominantly at C providing thermodynamically stable product. Although substitution also occurs at C in some kinetically controlled reactions.
Acetylation: Pyrrole treated with acetic anhydride at 200C gives 2-acetyl pyrrole while N-acetyl pyrrole cane be obtained by heating with N-acetyl imidazole. Oxidation & Reduction: Pyrrole oxidized to maleinimide by chromium trioxide (CrO ) in presence of acetic acid where as it catalytically reduced completely hydrogenate the ring system & produce pyrrolidine.
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