Derivatives of 3,4-Diphenylchromanes as Estrogens and Implantation Inhibitors

Synthesis of Chromans from the Reaction of O-quinone Methide Precursor with Substituted Styrenes

“…UV spectra were recorded on PU 8720 Philips spectra. 1 H and 13 C NMR spectra were determined at 500 and 75 MHz respectively using a Bruker AMX 500 spectrometer for solutions in deuteriochloroform. Mass spectra were recorded on VD-Autospec Fisana Instrument, Merk Kieselgel F 254 type 60 and Kieselgel 40-60 μm type were used for TLC and column chromatography.…”

“…2-Dimethylaminomethyl-4,5-dimethylphenol 4: The Mannich base (4) was prepared according to the method of Caldwell and Thompson. 13 3,4-Dimethylphenol (12.2 g, 0.1 mol) and dimethyl amine (35%, 5 ml, 0.1 mol) in ethyl alcohol (75 ml) were stirred at 25-35°C for 5 min. Formaldehyde (37%, 2.8 ml, 0.1 mol) was added dropwise to this mixture in 1 h and the mixture was left overnight to afford a white solid.…”

“…8a,b We intended to expand the synthesis to new chroman derivatives, 9,10 which are used as antiinflammatory agent, 11 in arthritis, 12 in anxiety 4 and used as antioxidants for fats and oils and some of them show weak estrogenic activity. 13 We decided to investigate the inverse electron demanded Diels-Alder cycloaddition reaction of the 2-naphtol 1 and 3,4-dimethylphenol Mannich bases 4 as the quinone-methides precursors 5 and 6 with (un) (R=H, o-, m-, p-CH 3 and Cl) substituted styrenes for the synthesis of 3,4dihydro-2-((un) substituted phenyl)-2H-benzo[f ]chromenes 7 (R=H, o-, m-, p-CH 3 and Cl) and 2-((un) substituted phenyl)-6,7-)dimethylchromans 10 (R=H, o-, m-, p-CH 3 and Cl). We aimed to investigate the effect of electron donating substituents in the benzenoid ring of the styrene to the yields in the synthesis of substituted 3,4-dihydro-2H-benzo[f ]chromenes 7 (R=H, o-, m-, p-CH 3 and Cl) and substituted-6,7-dimethylchromans 10 (R=H, o-, m-, p-CH 3 and Cl).…”