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Paper | Regular issue | Vol 104, No. 4, 2022, pp.739-750
Published online, 28th January, 2022
DOI: 10.3987/COM-21-14610
A New and Convenient Synthetic Method for 4-Aminoquinoline-3-carbonitrile and Its Derivatives

Amer Tarawneh*

*Chemistry and Chemical Technology, Department of Chemistry, Tafila Technical University, P.O.Box 179, Jordan

Abstract

A convenient approach is described for the general synthesis of 4-aminoquinoline-3-carbonitrile scaffolds. A series of substituted anthranilonitriles bearing electron-donating and-withdrawing groups on the arene react with 3-bromopropanenitrile and t-BuOK in anhydrous DMF at ca. 24 °C. A wide variety of bases have been used to optimize selective mono-N-alkylation. The best conditions lead to the corresponding 2-(cyanoethylamino)benzonitriles in moderate or good yields. Thorpe–Ziegler cyclization of the N-unprotected 2-(cyanoethylamino)benzonitrile analogs with t-BuLi in THF at -78 °C gives 4-amino, 4-amino-6-methyl, 4-amino-7-methyl, and 4-amino-6-fluoro-quinoline-3-carbonitriles in moderate yields. Owing to their vicinal amino and cyano functional groups that can function as enaminonitrile moieties, 4-aminoquinoline-3-carbonitriles are attractive building blocks frequently used in ring construction.