Reaction of enamines with 4-benzylidene-5-oxazolones

✍ Scribed by K.K. Prasad; D.S. Iyengar; R.V. Venkataratnam

• Book ID: 104236860
• Publisher: Elsevier Science
• Year: 1972
• Tongue: French
• Weight: 212 KB
• Volume: 13
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)84957-1

✦ Synopsis

We report a new reaction by which novel bicycle (3.3.1) nonane-2,9dione and 2-substituted tetrahydro-l-azaindan-3-ones can be prepared conveniently. This reaction which takes place between enamines derived from cyclohexanone and 4-benzylidene 5-oxazolones was carried out in dry benzene, from which the products were isolated by column chromatography over silica gel. t%-Acylamlno cinnamamides were also formed as coproducts and the reaction wise data are presented in the table. In this preliminary investigation of the reaction, it &as been found that the total amount of the products obtained after chromatographic separation constituted 30% of the reaction.

Besides the compounds reported here, several others were also obtained but in trace amounts, which have not been characterised.

While the structures of blcyclononadione (V) and lndanone derivatives (VIII) and (X1 have been determined, the structure of XI is yet to be worked out. These structural assignments as well as configurations of the acylamino cinnamamides follow from their spectral characteristics. The molar ratio of