4-Dimethylaminopyridine-catalyzed Cascade Reaction for Efficient Synthesis of Naphthofurans

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

FAN Chenli^1,2, HE Xinwei², LIAO Kaisheng², WANG Cui'e², SHANG Yongjia²

1. Department of Material Engineering, Wuhu Institute of Technology, Wuhu 241003, P. R. China;
2. Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Key Laboratory of Molecule-based Materials, College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, P. R. China

Received:2015-06-19 Revised:2015-08-27 Online:2016-02-01 Published:2015-10-19
Contact: SHANG Yongjia E-mail:shyj@mail.ahnu.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(Nos.21172001, 21372008), the Program for the New Century Excellent Talents in University of China(No.NCET-10-0004) and the Natural Science Foundation of Anhui Province of China(No.1308085QB39).

Abstract

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℃ 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 makes it practical and attractive.

Key words: 4-Dimethylaminopyridine, α-Halogenated ketone, Cascade reaction, Naphthofuran, Organocatalysis

FAN Chenli, HE Xinwei, LIAO Kaisheng, WANG Cui'e, SHANG Yongjia. 4-Dimethylaminopyridine-catalyzed Cascade Reaction for Efficient Synthesis of Naphthofurans[J]. Chemical Research in Chinese Universities, 2016, 32(1): 62-67.

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4-Dimethylaminopyridine-catalyzed Cascade Reaction for Efficient Synthesis of Naphthofurans

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