Bicyclic Guanidino Ketones Article

Houghten, RA, Simpson, RA, Hanson, RN et al. (1979). Bicyclic Guanidino Ketones . JOURNAL OF ORGANIC CHEMISTRY, 44(25), 4536-4543. 10.1021/jo00393a017

cited authors

  • Houghten, RA; Simpson, RA; Hanson, RN; Rapoport, H

authors

abstract

  • Syntheses of bicyclic [3.3.1] guanidino ketones are described by methods that permit the preparation of compounds substituted at the endo- and exocyclic nitrogen as well as at C-4. The primary synthetic method involved the synthesis of substituted and protected 3-aminopiperidones and their subsequent cyclization with S, S-dimethyl N-(p-toluenesulfonyl)dithiocarbonimidate to the substituted and protected bicyclic guanidino ketones. The ketones, blocked as the ethylene ketals, were deblocked by transketalization with cyclohexanone while the guanidine, blocked by tosylation, was deblocked by liquid HF. © 1979, American Chemical Society. All rights reserved.

publication date

  • January 1, 1979

published in

Digital Object Identifier (DOI)

start page

  • 4536

end page

  • 4543

volume

  • 44

issue

  • 25