Synthesis and CD spectral studies of some fused cholestenopyrimidines

Autor:	Naghmana Rashid, Wolfgang Voelter, Mashooda Hasan, Helmut Duddeck, Günther Snatzke
Rok vydání:	1994
Předmět:	chemistry.chemical_compound Pyrimidine chemistry Stereochemistry General Chemical Engineering General Chemistry Optically active Cholestanones Spectral line
Zdroj:	Pure and Applied Chemistry. 66:2057-2062
ISSN:	1365-3075 0033-4545
DOI:	10.1351/pac199466102057
Popis:	Synthesis of unsubstituted 5X'-cholesteno(3,2-d)- (5), (2,3-d)- (12), (3,4-d)(15) and 5.C- and 5 ~-cholest-3-eno(4,3-d)pyrimidines (21) and (21') has been achieved using hydroxymethylene derivatives of relevant cholestanones prepared from cholesterol(1). Their 2'-derivatives (5a - Se), (12a), (15a - 15c), (21a - 21c) and (21'a,21'b) could also be prepared. Attempts to prepare cholest-l-eno(l,2-d)pyrimdine system through 5X-cholestan-l-one(28) failed. 5 $-Cholest-6-eno(7,6-d)pyrimidine(33) was prepared by the reaction of cholestan-7-one with trisformylaminomethane. Three Cotton effects were observed between 350-200 nm in all these compounds intheir CD spectra. They have been assigned to n 3 K* and 7T -tT*transitions from long to short wave lengths. Quadrant rule has been applied for determining the sign of the first band CD, while helicity rule has been applied for the third band CD. Present work describes the synthesis of six series of optically active cholestenopyrimidines (Fig.l), e.g. 5 and its 2'-derivatives (5a-5e), 12 and its
Databáze:	OpenAIRE
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