4,4-Disubstituted 4H-isoxazol-5-ones bearing a 1,4-naphthoquinone moiety undergo transformation into different types of benzoindolyl products depending on the different reaction conditions. A decarboxylative ring opening/ring closure promoted by catalytic [Ru(p-cymene)2Cl2]2 yields benzo[f]indole-4,9-diones. Alternatively, hydrogenation reactions provide the conversion of 4-(1,4-naphthoquinone)-substituted isoxazol-5-ones to benzo[g]indole compounds, with the level of reduction depending on the substituents present on the ring. Starting materials have been easily prepared by the functionalization of isoxazolinones with naphthoquinone under mild conditions.

Divergent conversion of 4-Naphthoquinone-substituted 4 H-Isoxazolones to Different Benzo-fused Indole derivatives / M.S. Christodoulou, S. Giofre, E.M. Beccalli, F. Foschi, G. Broggini. - In: ORGANIC LETTERS. - ISSN 1523-7060. - 22:7(2020 Apr 03), pp. 2735-2739. [10.1021/acs.orglett.0c00709]

Divergent conversion of 4-Naphthoquinone-substituted 4 H-Isoxazolones to Different Benzo-fused Indole derivatives

M.S. Christodoulou
Primo
;
S. Giofre
Secondo
;
E.M. Beccalli;
2020

Abstract

4,4-Disubstituted 4H-isoxazol-5-ones bearing a 1,4-naphthoquinone moiety undergo transformation into different types of benzoindolyl products depending on the different reaction conditions. A decarboxylative ring opening/ring closure promoted by catalytic [Ru(p-cymene)2Cl2]2 yields benzo[f]indole-4,9-diones. Alternatively, hydrogenation reactions provide the conversion of 4-(1,4-naphthoquinone)-substituted isoxazol-5-ones to benzo[g]indole compounds, with the level of reduction depending on the substituents present on the ring. Starting materials have been easily prepared by the functionalization of isoxazolinones with naphthoquinone under mild conditions.
Settore CHIM/06 - Chimica Organica
3-apr-2020
Article (author)
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/727426
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