103281-94-3Relevant articles and documents
One-pot solvent-free synthesis of triaryl- and triheteroarylmethanes by Bi(OTf)3-catalyzed Friedel-Crafts reaction of arenes/heteroarenes with trialkyl orthoformates
Tuengpanya, Surisa,Chantana, Chayamon,Sirion, Uthaiwan,Siritanyong, Wipada,Srisook, Klaokwan,Jaratjaroonphong, Jaray
, p. 4373 - 4380 (2018)
A convenient, practical and highly efficient one-pot method has been developed for the synthesis of triaryl- and triheteroarylmethane derivatives by Bi(OTf)3-catalyzed Friedel-Crafts alkylation of trialkyl orthoformates in combination with a wide variety of arenes/heteroarenes at room temperature under solvent-free conditions and in an air atmosphere. The methodology offers an operational simplicity, high atom economy and environmentally benign procedure. Furthermore, selected compound 3k showed promising anti-inflammatory activity with inhibition nitric oxide and did not exhibit significant cytotoxic effects on macrophage cells.
Unusual Stabilities and Reactivities of Tris- and Bis(2,4,6-trimethoxyphenyl)carbenium Salts
Wada, Masanori,Konishi, Hideki,Kirishima, Katsuhiko,Takeuchi, Hiroshi,Natsume, Satoko,Erabi, Tatsuo
, p. 2737 - 2741 (2007/10/03)
2,4,6-Trimethoxyphenyllithium, Φ + ′Li[Φ + ′=2,4,6-(MeO)3C6H2], reacted with diphenyl carbonate and with ethyl formate to give tris(2,4,6-trimethoxyphenyl)methanol, Φ + ′3COH (1), and bis(2,4,6-trimethoxyphenyl)methanol, Φ + ′2CHOH (2), respectively. Compound 1 reacted with a slight excess of perchloric acid in 2-propanol to give very dark-purple crystals of the triarylcarbenium salt, [Φ + ′3C]X (3, X=ClO4), which were inert even in hot ethanol. However, a treatment of 3 (X=Cl), prepared in situ in 1 M (1 M=1 moldm-3) hydrochloric acid, with 1 M sodium hydroxide resulted to give 4-bis(2,4,6-trimethoxyphenyl)methylene-3,5-dimethoxy-2,5-cyclohexadienone. Compound 2 also reacted with a slight excess of perchloric acid in methanol to give dark-red crystals of the diarylcarbenium salt, [Φ + ′2CH]X (5, X=ClO4). Compound 5 was considerably inert even in hot methanol, but was easily reduced in primary and secondary alcohols to give bis(2,4,6-trimethoxyphenyl)methane, Φ + ′2CH2. Measurements of the half-lives of 5 in these alcohols showed that 5 was more labile in secondary alcohols, such as 2-propanol and 2-butanol, than in primary alcohols. When a suspension of 5 (X=Cl), prepared in situ in 1 M hydrochloric acid, was heated, tris(2,4,6-trimetrioxyphenyl)methane, Φ + ′3CH (7), was obtained. Analogous reactions to give 7 were observed in methanol containing a slight excess of hydrochloric acid or nitric acid in place of perchloric acid. The possible paths of these reactions are discussed.
