ANALOGUES OF LAPACHOL AS ANTITUMOR AGENTS

摘要

1,268,316. 2-Allyl-3-hydroxy-1,4-naphthoquinone derivatives. PFIZER Inc. 5 May, 1970 [2 March, 1970], No. 21669/70. Heading C2C. Novel 2-allyl-3-hydroxy-1,4-naphthoquinone derivatives of the general formula wherein each R is a halogen atom or a trifluoromethyl group or the two Rs together form a C 3-6 carbocyclic ring, which have antitumour activity, are prepared by reaction of a 2- hydroxy-1,4-naphthoquinone salt of the general formula with an allyl halide of the general formula XCH 2 CH=C(R) 2 orCH 2 =CH-CX(R) 2 , wherein X is a chlorine, bromine or iodine atom, in the presence of a metal iodide and a solvent. 3,3-Bis-(trifluoromethyl)-allyl iodide is prepared by reaction of vinyl magnesium chloride with hexafluoroacetone in tetrahydrofuran with external cooling, treatment of the resulting complex with saturated ammonium chloride solution, reaction of the resulting 1,1,1-trifluoro- 2-trifluoromethyl-3-buten-2-ol with p-bromobenzenesulphonyl chloride in the presence of sodium hydride and reaction of the resulting 1,1-bis- (trifluoromethyl)-allyl p-bromobenzenesulphonate with potassium iodide.