4,4-Dimethyl-2-(2-lithio-4-(trifluoromethyl)phenyl)-2-oxazoline reacted with 2-and 1-naphthaldehydes to afford, after hydrolysis, 3-(2-naphthyl)-5-(trifluoromethyl)phthalide ( 6) and 3-(l-naphthyl)-5-(trifluoromethyl)phthalide (7), respectively. Hydriodic acid reduction of these phthalides yielded 2-(2-naphthylmethyl)-4-(trifluoromethyl)benzoic acid (8) and 2-(1 -naphthylmethyl)-4-(trifluoromethyl)benzoic acid (9), which were cyclized and oxidized to 9-(trifluoromethyl)-7,12-benz[o]anthraquinone (10) and 10-(trifluoromethyl)-7,12-benz[a]anthraquinone ( 11), respectively. Reaction of these quiñones with methyllithium followed by stannous chloride-hydrochloric acid reduction of the resulting diols gave 9-(trifluoromethyl) -7,12-dimethylbenz [o ] anthracene (12) and 10-(trifluoromethyl)-? ,12-dimethylbenz [a] anthracene (13), respectively. In a different route, 2-(3-(trifluoromethyl)benzoyl)-l-naphthoic acid (15), prepared from m-(trifluoromethyl)phenylmagnesium bromide ( 14) and 1,2-naphthalic anhydride, was reacted with methylmagnesium bromide to obtain 2-[1-hydroxy-1-(3-(trifluoromethyl)phenyl)ethyl]-1-naphthoic acid lactone (16). Zinc-alkali reduction of 16 yielded 2-[l-(3-(trifluoromethyl)phenyl)ethyl]-l-naphthoic acid (17), the acid chloride of which afforded l-acetyl-2-[l-(3-(trifluoromethyl)phenyl)ethyl]naphthalene (18) on treatment with lithium dimethylcuprate. Although 2-[(3-(trifluoromethyl)phenyl)hydroxymethyl]-l-naphthoic acid lactone (19), obtained by the reduction of 15 with triethylsilane, underwent a reductive ring closure to 9-(trifluoromethyl)benz[o]anthracene (20), attempted cyclization of 18 did not yield the anticipated 12.
First published in 1988, this volume surveys the chemical synthesis and biological activity of the benz[a]anthracenes. These compounds occur in smoke and mineral oils and a few have been shown to be potent carcinogens. This volume was the first to review, systematically and in depth, the organic synthesis of these compounds as well as their metablolism, interactions with nucleic acids and protein, mutagenicity and carcinogenicity. Such studies have important implications in determining mechanism and specificity of chemically induced carcinogenesis.
Pyridazine and pyrimidine have been reacted with trimethylsilyl cyanide and benzoyl chloride to give the first examples of Reissert compounds derived from monocyclic systems.
Mit Trimethylsilylcyanid (II) und Säurechloriden (III) entstehen aus den Isochinolinen (I) glatt die Reissert‐Verbindungen (IV), die zu (V) alkyliert werden können.
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