Synthesis of 1-acyl-2-oxo-3-pyrrolidinecarbonitriles by the reaction of 2-acylamino-4,5-dihydro-3-furancarbonitriles with sodium iodide

Abstract

The reaction of 2‐acylamino‐4,5‐dihydro‐3‐furancarbonitriles 1 with sodium iodide in N,N‐dimethyl‐formamide gave the corresponding 1‐acyl‐2‐oxo‐3‐pyrrolidinecarbonitriles 2 in good yields. Successive treatment of 1 with titanium(IV) chloride and potassium carbonate resulted in the formation of N‐acyl‐1‐cyanocyclopropanecarboxamides 4. The same compounds 2 were also obtained by treatment of 4 with sodium iodide. The starting compounds 1 were synthesized by the reaction of 2‐amino‐4,5‐dihydro‐3‐furan‐carbonitrile with acyl chlorides in pyridine.

Synthesis of α‐Diaminomethylenebutyrolactams by the Reaction of α‐Cyanobutyrolactams with N‐Trimethylsilylamines.

“…N-Trimethylsilylamines used in this study include N-trimethylmorpholine, N-trimethylsilylpyrrolidine and N-trimethylsilyldimethylamine. The starting compounds 1 were prepared by a procedure described in the literature [18]. When a mixture of 1-benzoyl-2-oxo-3-pyrrolidinecarbonitrile (1a) and N-trimethylsilylmorpholine in 1,2dichloroethane was stirred at room temperature, 3-(amino-(morpholino)methylene)-1-benzoyl-2-pyrrolidinone (2a) was obtained in 79% yield.…”