Amidines of Certain Substituted Triphenylethylenes

Abstract

The conversion of certain bromo substituted triphenylethylenes via cyano-and ethyl imidate hydrochloride derivatives to the corresponding guanyl (amidino) substituted triphenylethylenes has been accomplished. Unsubstituted amidines, N-alkyl-, , -dialkyland N,N'-dialkylamidines were prepared and the amidine group was incorporated into various heterocyclic substituents. Structural modifications of the triphenylethylene moiety gave rise to amidine derivatives of triphenylethane, triphenylhaloethylene and 9-benzalfluorene. When cis-trans isomerism was possible, separation of isomers could be effected by fractional crystallization of the intermediate nitriles. A number of the amidines exhibited anti-inflammatory and antifungal activities.

Original Synthesis of Fluorenyl Alcohol Derivatives by Reductive Dehalogenation Initiated by TDAE

“…1 H-NMR (200 MHz) (CDCl 3 ) 7.97–7.94 (m, 1H); 7.75–7.73 (m, 1H); 7.41–7.30 (m, 6H); 7.12 (d, J = 8.3 Hz, 2H); 7.12 (d, J = 8.3 Hz, 2H); 6.80 (bs, 1H). Physical and spectroscopic data agree with those reported in the literature [38].…”

Sunlight‐Driven Synthesis of Triarylethylenes (TAEs) via Metal‐Free Mizoroki–Heck‐Type Coupling

“…4‐[2,2‐Bis(4‐chloro‐phenyl)‐vinyl]benzonitrile (6a): From 50 mg (0.03 m , 0.24 mmol) of 1a, 239 mg (0.12 m , 0.96 mmol) of 1,1′‐(ethenylidene)‐bis(4‐chlorobenzene) in dry MeCN (8 mL). Purification by flash chromatography afforded 32 mg of 6a (white solid, 28 % yield, mp: 115‐116 °C, lit . 117‐118 °C).…”

Imidates

“…(1) is still widely used and consists of condensing a nitrile with an alcohol under anhydrous conditions at 0°C in the presence of hydrogen chloride or bromide [ l a , b ] . Solvents such as ether [28], dioxane [29], dimethyl cellosolve [30], chloroform [22g], benzene [31] and nitrobenzene [22g] are sometimes employed as diluents and as an aid to crystallization of the imidate salt. The use of excess alcohol may cause ortho ester formation.…”