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Synthesis and stereochemistry of dispiro substituted pyridazines: Application of ellipticity‐absorbance ratio spectra for proving enantiomeric relationship by HPLC‐CD/UV detection
Author(s) -
Beke Gyula,
Gergely András,
Szász György,
Szentesi Aletta,
Nyitray József,
Barabás Orsolya,
Harmath Veronika,
Mátyus Péter
Publication year - 2002
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.10096
Subject(s) - chemistry , enantiomer , absorbance , high performance liquid chromatography , chiral column chromatography , stereochemistry , spectral line , chromatography , organic chemistry , physics , astronomy
The aim of our study was to synthesize vinylic and pyrido‐fused pyridazines with a spirano moiety and to investigate their stereochemistry by spectroscopic and HPLC analyses. The vinylic compounds 5 were obtained by Knoevenagel condensation of cyclohexylidene malonates 1 with pyridazinecarbaldehyde 2 . Compound 5b exhibits geometric isomerism identified by NMR, HPLC, and X‐ray methods. The thermal rearrangement reactions of compounds 5 easily led to the pyridopyridazine derivatives 6 . In the case of 6b , possessing both central and axial chirality, both diastereomers and the respective enantiomers were detected. Their stereochemical relationships could be determined by HPLC‐CD/UV analyses with application of anisotropy spectra in a novel way. Chirality 14:365–371, 2002. © 2002 Wiley‐Liss, Inc.