Citation: Ru Shu Sun, Yang Wang, Peng Xia. Studies on the esterifications of 9-(hydroxyimino)-4-methyl-8,9-dihydrofuro[2,3-h]chromen-2-one with acid chlorides under different conditions[J]. Chinese Chemical Letters, ;2008, 19(7): 791-794. doi: 10.1016/j.cclet.2008.04.038 shu

Studies on the esterifications of 9-(hydroxyimino)-4-methyl-8,9-dihydrofuro[2,3-h]chromen-2-one with acid chlorides under different conditions

Department of Medicinal Chemistry, School of Pharmacy, Fudan University, Shanghai 200032, China

Received Date: 18 January 2008

The esterifications of 9-(hydroxyimino)-4-methyl-8,9-dihydrofuro[2,3-h]chromen-2-one (4) with acid chlorides afforded normal oxime-esters 3a-e in 35-78% yields in presence of excessive 4-dimethylaminopyridine as the acid scavenger,whereas the reactions gave unexpected 8-substituted products N-(8-chloro-4-methyl-2-oxo-2H-furo-[2,3-h]chromen-9-y1)amides (5a-c)and 4-methyl-2,9-dioxo-8,9-dihydro-2H-furo[2,3-h]chromen-8-ylcarboxyloates (6d-e) by using excessive acid chlorides.The structures of 10 new compounds were determined by ¹H NMR,¹³C NMR,MS and HRMS,and the possible mechanism for the formation of unexpected products 5a-e and 6d-e was also proposed.
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