Solid-phase synthesis of 1,5-disubstituted 2-aryliminoimidazolidines Article

Yu, Y, Ostresh, JM, Houghten, RA. (2002). Solid-phase synthesis of 1,5-disubstituted 2-aryliminoimidazolidines . JOURNAL OF ORGANIC CHEMISTRY, 67(9), 3138-3141. 10.1021/jo0109366

cited authors

  • Yu, Y; Ostresh, JM; Houghten, RA

abstract

  • 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 arylisothlocyanates in the presence of mercuric chloride (HgCl2) 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 °C gave the desired products in good yield and purity. The preparation of a large combinatorial library of such compounds is also discussed.

publication date

  • May 3, 2002

published in

Digital Object Identifier (DOI)

start page

  • 3138

end page

  • 3141

volume

  • 67

issue

  • 9