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The Cyclization and Functionalization Reactions Involving N-Phenacylpyridinium Salts Publisher



Doraghi F1 ; Serajian A2 ; Karimian S3 ; Larijani B1 ; Mahdavi M1
Authors
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Authors Affiliations
  1. 1. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran
  2. 2. Department of Chemistry, Institute for Advanced Studies in Basic Sciences (IASBS), Zanjan, Iran
  3. 3. Medicinal and Natural Products Chemistry Research Center, Shiraz University of Medical Sciences, Shiraz, Iran

Source: Chemical Papers Published:2024


Abstract

Pyridinium salts have been used as starting materials and intermediates in 1,3-dipolar cycloaddition with dipolarophiles. Among them, N-phenacylpyridinium salts can easily react with dipolarophiles due to having a good electron-attracting COPh group. This group can stabilize pyridinium ylide generated in situ from N-phenacylpyridinium salts. The synthesis of a wide variety of biologically active N-, O-, and S-heterocycles, as well as carbocycles, can be achieved from N-phenacylpyridinium salt precursors. This review highlights important cyclization and functionalization reactions, involving N-phenacylpyridinium salts. Graphical abstract: N-phenacylpyridinium salts, an important subclass of pyridinium salts, serve as an intermediate, as well as a starting material in the synthesis of a diverse range of N-, O-, and S-heterocycles, as well as carbocycles. The construction of important biologically active molecules, such as indolizine, pyridine, quinoline, pyrrole, azepine, dihydrofuran, and chromene, can be achieved from N-phenacylpyridinium salt precursors. This review highlights cyclization and functionalization reactions, involving N-phenacylpyridinium salts. (Figure presented.) © The Author(s), under exclusive licence to the Institute of Chemistry, Slovak Academy of Sciences 2024.