[7-aza analogs of quinazolino-carboline alkaloids. Synthesis, structure, characterization].
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 quasi-equatorial position. Semiempirical MO calculations support these conformational preferences.
Kökösi
J
J
Semmelweis Egyetem, Gyógyszerészi Kémiai Intézet, Budapest, H-1092, Hógyes E. u. 9.
Kiss
A
A
Rotter
R
R
Hermecz
I
I
Noszál
B
B
D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry*; D001372:Aza Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D002243:Carbolines / Q000138:chemical synthesis / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D011799:Quinazolines / Q000138:chemical synthesis / Q000737:chemistry*
D000470:Alkaloids; D001372:Aza Compounds; D002243:Carbolines; D011799:Quinazolines