The synthesis, structure and characterization of 8-substituted-7-azarutaecarpines (2) is described. These compounds were prepared by Fischer indolization of 3-amino-2-(1-phenylhydrazonoethyl)-4(3H)-quinazolin-one (5), followed by cyclocondensation with a series of aliphatic or aromatic aldehydes and formic acid or a Vilsmeyer-Haack reagent. The stereochemistry of compounds (2) was investigated by 1H nmr spectroscopy. It was found that the 8-substituents assume a quasi-axial position on the flattened boat conformation of ring C of (2), with the exception of ortho substituted phenyl groups, which occupy quasiequatorial position. Semiempirical MO calculations support these conformational preferences.
|Number of pages||9|
|Journal||Acta pharmaceutica Hungarica|
|Publication status||Published - Dec 1 2000|
ASJC Scopus subject areas
- Pharmaceutical Science