A lewis acid-promoted cyclization of ethenetricarboxylate derivative aromatic compounds. Novel syntheses of oxindoles and benzofuranones via friedel-crafts intramolecular michael addition

Organic and Biomolecular Chemistry

Volumn 2, Issue 21, 2004, Pages 3134-3138

  Yamazaki, Shoko ^a   Morikawa, Satoshi ^a   Iwata, Yuko ^a   Yamamoto, Machiko ^a   Kuramoto, Kaori ^a  

^a NARA UNIVERSITY OF EDUCATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CATALYSIS; CHEMICAL BONDS; DERIVATIVES; MIXTURES; SUBSTRATES; SYNTHESIS (CHEMICAL);

CYCLIZATION; LEWIS ACIDS; OXINDOLES; RING-FORMING REACTIONS;

AROMATIC COMPOUNDS;

EID: 9144233089     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b408728c     Document Type: Article

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40. The optimized reaction conditions are as follows. The 1,1-diester of 2-hydrogen ethenetricarboxylate was reacted with 1-hydroxybenzotriazole (HOBT) in the presence of EDCI for 1 h at 0°C, then the corresponding N-alkyl aniline was added and the resulting mixture stirred at room temperature overnight. When all the reagents were mixed at once (see Electronic supplementary information†), considerable amounts of byproducts 12 were produced and the yields of 1 decreased. Probably Michael addition of the corresponding N-alkyl anilines to 1,1-diester of 2-hydrogen ethenetricarboxylate occurred before condensation of the carboxyl group and the aniline. The reaction with N-unsubstituted aniline under the conditions gave diester amide 1 only in very low yield.
41. The yield (65%) contains small amounts of unidentified byproducts which could not be removed by column chromatography. Pure 4a was isolated in 36% yield.