ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

The cyclization and functionalization reactions involving N-phenacylpyridinium salts

Fatemeh Doraghi, Azam Serajian, Somaye Karimian, Bagher Larijani, and Mohammad Mahdavi

Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran

E-mail: momahdavi@tums.ac.ir

Received: 18 March 2024  Accepted: 2 July 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.

Keywords: N-phenacylpyridinium salt; Dipolarophiles; Heterocycles; Cyclization

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-024-03593-1

Chemical Papers 78 (12) 6821–6841 (2024)