Reaction of pyridazine and quinoline with silyl enol ethers in the presence of alkyl chloroformate
Pyridazine was allowed to react with silyl enol ethers (or ketene silyl acetals) in the presence of ethyl chloroformate to give 4- and 6-substituted 1-ethoxycarbonyldihydropyridazines in good yields. The vicinal substituents of silyl enol ethers considerably affected the regioselectivity, and one of the two dihydroadducts was selectively obtained by the use of appropriate silyl enol ethers. Similar substituent effect was observed in the reaction of quinolines under the same conditions.
INTRODUCTION OF β-KETOALKYL GROUPS AT 4-POSITION OF PYRIDINE USING SILYL ENOL ETHERS
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Akiba, Kin-ya,Nishihara, Yoshihiro,Wada, Makoto
p. 536
(2007/10/02)
REGIOSELECTIVE SYNTHESIS OF 4-(2-OXOALKYL)PYRIDINES VIA 1,4-DIHYDROPYRIDINE DERIVATIVES USING SILYL ENOL ETHERS AND PYRIDINIUM SALTS
Trimethylsilyl enol ethers (1) reacted with 1-ethoxycarbonylpyridinium chloride (3) at 4-position with high regioselectivity to afford 1-ethoxycarbonyl-4-(2-oxoalkyl)-1,4-dihydropyridines (4) in 42-87percent yields.When 2,2,2-trichloroethyl chloroformate
Akiba, Kin-ya,Nishihara, Yoshihiro,Wada, Makoto
p. 5269 - 5272
(2007/10/02)
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