4-dimethylaminopyridine-catalyzed cascade reaction for efficient synthesis of naphthofurans

Chenli Fan; Xinwei He; Kaisheng Liao; Cui’e Wang; Yongjia Shang

doi:10.1007/s40242-016-5245-0

Chemical Research in Chinese Universities ›› 2016, Vol. 32 ›› Issue (1) : 62 -67. DOI: 10.1007/s40242-016-5245-0

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4-dimethylaminopyridine-catalyzed cascade reaction for efficient synthesis of naphthofurans

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Abstract

A convenient and efficient method was developed for the synthesis of naphtho[2,1-b]furans via 4-dimethylaminopyridine(DMAP)-catalyzed cascade reaction of 2-hydroxy-1-naphthaldehydes and α-halogenated ketones in moderate to good yields in the presence of Na₂CO₃ at 80 ºC for 6 h. The mechanism for this process was briefly discussed with a tentative catalytic cycle proposed. Moreover, this method features organocatalysts and high step-economy, which make it practical and attractive.

Keywords

4-Dimethylaminopyridine / α-Halogenated ketone / Cascade reaction / Naphthofuran / Organocatalysis

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Chenli Fan, Xinwei He, Kaisheng Liao, Cui’e Wang, Yongjia Shang. 4-dimethylaminopyridine-catalyzed cascade reaction for efficient synthesis of naphthofurans. Chemical Research in Chinese Universities, 2016, 32(1): 62-67 DOI:10.1007/s40242-016-5245-0

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