- A stereoselective synthesis of (E)-1-halo-6,6-dimethyl-2-hepten-4-yne: A key intermediate for terbinafine
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A study of the stereoselective halogenation of 6,6-dimethyl-1-hepten-4- yn-3-ol (1) using a series of halogenating agents is described. Of the many agents investigated, boron trichloride is the most successful reagent for stereoselective halogenation (E:Z=9:1(max)). The resulting (E)-1-halo-6,6- dimethyl-2-hepten-4-yne (2), a key intermediate for terbinafine, an antifungal agent, is obtained in good yield and stereoselectivity. Two structurally related enyne alcohols have been studied likewise and shown similar versatility. (C) 2000 Elsevier Science Ltd.
- Chou, Shan-Yen,Tseng, Chin-Lu,Chen, Shyh-Fong
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- A PROCESS FOR THE PURIFICATION OF 1-HALO-6,6-DIMETHYL-HEPT-2-ENE-4-YNE
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The invention relates to a process for purification of 1-halo-6,6-dimethyl-hept-2-ene-4-yne of Formula (I), wherein X represents a halogen atom subjecting crude 1-halo-6,6-dimethyl-hept-2-ene-4-yne to distillation under reduced pressure to obtain pure 1-halo-6,6-dimethyl-hept-2-ene-4-yne. This compound is an important intermediate for the production of the widely used antifungal drug Terbinafine.
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- Process for the preparation of terbinafine and salts thereof
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A process for the preparation of Terbinafine and salts thereof by reacting 1-chloro-6,6-dimethylhept-2-en-4-yne and N-methyl-N-(1-naphthylmethyl)amine in a basic aqueous medium is disclosed. Also disclosed is a process for the preparation of 1-chloro-6,6-dimethylhept-2-en-4-yne.
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- PROCESS FOR PREPARING A SUBSTITUTED ALLYLAMINE DERIVATIVE AND THE SALTS THEREOF
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The antifungal agent (E)-N-methyl-N-(1-naphthylmethyl)-6,6-dimethyl-hept-2-ene-4-ynyl-1-amine of formula (I)and acid addition salts thereof are prepared by reacting a chloro-compound of formula (IIIb)with a secondary amine of formula (II)in an aliphatic ketone-type solvent in the presence of a base and optionally iodide salt catalyst, and subsequently treating the resulting reaction mixture directly with aqueous hydrochloric acid to precipitate the hydrochloride of the compound of formula (I). The precipitate is separated, and the base of formula (I) can be liberated from the hydrochloride and can be converted into other pharmaceutically acceptable acid addition salts.
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- Pyrazole compounds, insecticidal and acaricidal compositions and use
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There are disclosed a pyrazole compound represented by the formula, STR1 wherein the substituents of R1 to R8 and the symbol Z have the specified meanings as described in the text, an insecticidal and acaricidal composition containing the same, use of said composition for control of insects and mites and a method of preparing said compound, and its intermediate.
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- Intermediate compounds for an insecticidal and acaricidal pyrazole compound
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There are disclosed intermediate compounds of the formula, STR1 wherein the substitutents of R1 to R7 and R9 have the same meanings as described in the text, for producing a insecticidal and acaricidal pyrazole compound represented by the formula, STR2 wherein the substituents of R1 ' to R8 and the symbol Z have the specified meanings as described in the text.
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