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Acid-Catalyzed Air-Oxidative Fragmentation of the Carbon-Carbon Bond in 2-Aryl-1-tetralones.

ABSTRACT: Catalytic auto-oxidation with air is a highly desirable method for green synthesis. Described here is a method for acid-catalyzed one step air-oxidative fragmentation of 2-aryl-1-tetralones to alkyl-2-(3-oxo-3-aryl) benzoates in the presence of alcohol. This method was then demonstrated using concise synthesis of a key intermediate of antiasthma drug Montelukast sodium. Moreover, the paradoxical nature of the reaction in which ester forms but only within a low concentration threshold of alcohol helps in understanding the mechanism of the reaction.

SUBMITTER: Ghosh P

PROVIDER: S-EPMC6648412 | biostudies-literature | 2019 May

REPOSITORIES: biostudies-literature

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Acid-Catalyzed Air-Oxidative Fragmentation of the Carbon-Carbon Bond in 2-Aryl-1-tetralones.

Ghosh Partha P

ACS omega 20190502 5

Catalytic auto-oxidation with air is a highly desirable method for green synthesis. Described here is a method for acid-catalyzed one step air-oxidative fragmentation of 2-aryl-1-tetralones to alkyl-2-(3-oxo-3-aryl) benzoates in the presence of alcohol. This method was then demonstrated using concise synthesis of a key intermediate of antiasthma drug Montelukast sodium. Moreover, the paradoxical nature of the reaction in which ester forms but only within a low concentration threshold of alcohol ...[more]

PMID: 31459896

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