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Synthesis 2008(17): 2686-2694  
DOI: 10.1055/s-2008-1067206
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Manganese(III)-Mediated Direct Introduction of 3-Oxobutanamides into Methoxynaphthalenes

Zhi-qi Cong, Hiroshi Nishino*
Department of Chemistry, Graduate School of Science and Technology, Kumamoto University, Kurokami 2-39-1, Kumamoto 860-8555, Japan
Fax: +81(96)3423374; e-Mail: nishino@sci.kumamoto-u.ac.jp;
Further Information

Publication History

Received 18 March 2008
Publication Date:
24 July 2008 (online)

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Abstract

The oxidation of methoxynaphthalenes with manganese(III) acetate in the presence of N-aryl-3-oxobutanamides gave the directly 3-oxobutanamide-substituted methoxynaphthalenes in moderate to good yields along with small amounts of naphtho[2,1-b]furans and benzo[e]indolinones. The optimized reaction conditions and the mechanism for the formation of the products are discussed.

Key words

oxidations - manganese - radicals - aromatic substitutions - cyclizations

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9

The total yield of the products 3aa, 4aa, and 5aa was 48% (entry 1), 54% (entry 2), and 57% yield (entry 3), respectively.