- An expedient synthesis of cyanoformates via DAST-mediated C–C bond cleavage of α-oximino-β-ketoesters
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A new protocol to synthesize cyanoformates was developed using simple β-ketoesters as substrates. (Diethylamino)sulfur trifluoride (DAST) was used as a dual-role reagent to activate the oxime moiety and to donate a fluoride. The key intermediates, α-oximino-β-ketoesters, were prepared by highly efficient acid-assisted oximation of β-ketoesters. Then, the deconstruction of α-oximino-β-ketoesters by the fluorinative C–C bond cleavage was demonstrated to provide cyanoformates. In this event, the fluoride addition followed by the C–C bond cleavage selectively occurred in the ketones over esters. Due to simple and mild reaction conditions, variously functionalized cyanoformates were exemplified.
- Kim, Danhee,Lim, Hee Nam
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supporting information
(2021/05/10)
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- HETEROARYL DERIVATIVES AS SEPIAPTERIN REDUCTASE INHIBITORS
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Inhibitors of sepiapterin reductase of formula (I) or (I'), wherein the substituents are defined as in the claims, and uses of sepiapterin reductase inhibitors in analgesia, treatment of acute and chronic pain, anti-inflammation, and immune cell regulation are disclosed.
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Paragraph 00925-00927
(2017/05/31)
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- Process for producing cyanoformate esters
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Alkyl, aralkyl or aryl cyanoformate esters having from one to 20 carbon atoms are prepared by anhydrously reacting stoichiometric amounts of the corresponding alkyl, aralkyl or aryl haloformate and an organosilyl nitrile in the presence of a catalytic amount of a tertiary amine base, preferably 1,4-diazabicyclo?2.2.2!octane, in the absence or presence of an inert solvent. The reaction is conducted at a temperature of from about -30° C. to 70° C., preferably at from about 5° C. to 30° C.
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