Solid-phase synthesis of 1,5-disubstituted 2-aryliminoimidazolidines.
The solid-phase synthesis of 1,5-disubstituted 2-aryliminoimidazolidines, starting from resin-bound N-acylated amino acid amides, is described. Exhaustive reduction of resin-bound acylated amino acid amides with borane-THF afforded the corresponding disecondary amines. Further reaction with arylisothiocyanates in the presence of mercuric chloride (HgCl(2)) yielded the corresponding resin-bound 1,5-disubstituted 2-aryliminoimidazolidines. Cleavage of the product from the resin using HF/anisole (95/5) for 1.5 h at 0 degrees C gave the desired products in good yield and purity. The preparation of a large combinatorial library of such compounds is also discussed.
Yu
Yongping
Y
Torrey Pines Institute for Molecular Studies, 3550 General Atomics Court, San Diego, California 92121, USA.
Ostresh
John M
JM
Houghten
Richard A
RA
D000577:Amides / Q000138:chemical synthesis; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D007093:Imidazoles / Q000138:chemical synthesis*; D007097:Imines / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism
D000577:Amides; D007093:Imidazoles; D007097:Imines