METHOD FOR PRODUCTION OF ALPHA-ARYLALKANECARBOXYLIC ACIDS

FIELD: organic chemistry. ^ SUBSTANCE: invention relates to new method for production of m- or p-substituted alpha-arylalkanecarboxylic acids of general formula I ^ from respective alpha-hydroxylated derivatives using inexpensive reagents and without converting of any reducible groups such as ester...

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Hauptverfasser: MANTOVANINI MARKO, ALLEGRETTI MARCHELLO, CHESTA MARIJA KANDIDA, NIKOLINI LUKA
Format: Patent
Sprache:eng ; rus
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Zusammenfassung:FIELD: organic chemistry. ^ SUBSTANCE: invention relates to new method for production of m- or p-substituted alpha-arylalkanecarboxylic acids of general formula I ^ from respective alpha-hydroxylated derivatives using inexpensive reagents and without converting of any reducible groups such as ester or ketone ones in side chains. In formula R is hydrogen, C1-C6-alkyl; R1 is hydrogen, linear or branched C1-C6-alkyl, phenyl, p-nitrophenyl, alkali or earth-alkali cation or cation of pharmaceutically acceptable ammonia salt: A is C1-C4-alkyl, aryl, optionally substituted with one or more alkyl, hydroxy, etc., aryloxy, arylcarbonyl; A is in m- or p-sites; P - linear or branched C1-C6-flkyl, phenyl, nitrophenyl. Claimed method includes the next steps: a) converting of compounds of formula II to compound of formula III either by reaction of II with compound of formula in presence of organic or inorganic base or by reaction of II with thiophene of formula and followed by reaction of obtained product with HNRaRb, wherein Ra and Rb are as defined above; b) thermal rearrangement of III to form IIIb ; c) catalytic dehydration of IIIb to form IIIc ; and d) optional hydrolysis of IIIc to obtain target compound of formula I. Also are disclosed new compounds of formulae III and IIIb. ^ EFFECT: new alpha-arylalkanecarboxylic acids and intermediates thereof. ^ 6 cl, 5 ex