Synthesis and Properties of 3-Cynnamoyl-4-hydroxy-2-quinolone

Condensation of 3-acetyl-4-hydroxy-2-quinolone with aromatic aldehydes gave substituted 3-cynnamoyl-4-hydroxy-2-quinolones that luminesce in the solid state in the visible spectral range.     

Selective conversion of the oximes of pinocamphone and isopinocamphone into bicyclic lactams

A method is proposed for the selective conversion of oximes of terpene ketones of the pinane (2,6,6-trimethylbicyclo[3.1.1]heptane) series into the corresponding bicyclic lactams which consists in the action on these oximes of sulfuric acid in a weak nucleophile — a nitrile. The fact that the interaction takes place through the stage of formation of N-acylamidines — products of the nucleophilic stabilization of the intermediate carbocations — permits the rearrangement of the latter and the formation of monocyclic products to be avoided, which makes it possible to obtain in good yields bicyclic lactams, the synthesis of which by other methods is problematical.Institute of Physical Organic Chemistry, Belarus Academy of Sciences, Minsk. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 365–369, May–June, 1993.     

Selective conversion of the oximes of pinocamphone and isopinocamphone into bicyclic lactams

A method is proposed for the selective conversion of oximes of terpene ketones of the pinane (2,6,6-trimethylbicyclo[3.1.1]heptane) series into the corresponding bicyclic lactams which consists in the action on these oximes of sulfuric acid in a weak nucleophile — a nitrile. The fact that the interaction takes place through the stage of formation of N-acylamidines — products of the nucleophilic stabilization of the intermediate carbocations — permits the rearrangement of the latter and the formation of monocyclic products to be avoided, which makes it possible to obtain in good yields bicyclic lactams, the synthesis of which by other methods is problematical.     

Synthesis of 2,5,5-trimethylcycloheptanone

The synthesis of 2,5,5-trimethylcycloheptanone from 3-carene was described. It was demonstrated that hydrogenolysis of cis-caran-trans-4-ol on nickel-and copper-containing catalysts occurred with cleavage of the internal C¹–C⁶ bond of the cyclopropane ring and predomonant (up to 95%) formation of 2,5,5-trimethylcycloheptanone. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 53–55, January–February, 2007.