20312-83-8Relevant articles and documents
An efficient, mild and scalable synthesis of bioactive compounds containing the angelicin scaffold
Shiao, Hui-Yi,Kuo, Ching-Chuan,Horng, Jim-Tong,Shih, Shin-Ru,Chang, Sui-Yuan,Liao, Chun-Chen,Hsu, John T.-A.,Amancha, Prashanth Kumar,Chao, Yu-Sheng,Hsieh, Hsing-Pang
, p. 1548 - 1554 (2013/03/28)
An efficient, mild and scalable synthesis of angelicin scaffold based compounds was developed. Particularly, the new synthetic route described here circumvents the need for the previously reported key Fries rearrangement step, which uses impractically har
Intermolecular character of the Fris rearrangement in the series of acyloxycoumarins
Kravchenko,Chibisova,Traven'
, p. 899 - 909 (2007/10/03)
In the study of the Fris rearrangement in the series of 7-and 4-acyloxycoumarins we obtained certain data indicating intermolecular character of the rearrangement. The Fris rearrangement of a mixture of 7-benzoyloxy-4-metylcoumarin and 7-acetoxycoumarin results in formation of four reaction products in approximately equal molar ratio. Also, four products were obtained in the Fris rearrangement of 7-and 4-acyloxycoumarins in the presence of hydroxycoumarins. The Fris rearrangement of acyloxycoumarins in the presence of m-xylene at acylcoumarin-m-xylene ratio of 1:6 leads to the corresponding hydroxycoumarins and acylated m-xylenes. Intermediate formation of acylium ions was also detected by evolution of carbon monooxide at the Fris rearrangement of 7-pyvaloyloxy-and 7-isobutyryloxy-4-methylcoumarins. A product of intermolecular migration, 3-acetyl-4-hydoxy-6-methylcoumarin, was discovered also in the rearrangement of 4-acetoxycoumarin in the presence of 4-hydoxy-6-methylcoumarin catalyzed by phosphorus oxychloride.