Synthesis 2019; 51(17): 3259-3268
DOI: 10.1055/s-0037-1611564
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Phenyl-2,2′-bichalcophenes and Their Aza-Analogues by Catalytic Oxidative Deacetylation

Xia Jiang
a   School of Pharmacy, East China University of Science and Technology, Meilong Road 130, Shanghai 200237, P. R. of China
b   Department of Energy Science and Technology, Myongji University, Myongji-Ro 116, Cheoin-Gu, Yongin, Gyeonggi-Do 17058, Korea
,
Hui Jin
a   School of Pharmacy, East China University of Science and Technology, Meilong Road 130, Shanghai 200237, P. R. of China
b   Department of Energy Science and Technology, Myongji University, Myongji-Ro 116, Cheoin-Gu, Yongin, Gyeonggi-Do 17058, Korea
,
Tingshu Wang
a   School of Pharmacy, East China University of Science and Technology, Meilong Road 130, Shanghai 200237, P. R. of China
b   Department of Energy Science and Technology, Myongji University, Myongji-Ro 116, Cheoin-Gu, Yongin, Gyeonggi-Do 17058, Korea
,
Hyebin Yoo
b   Department of Energy Science and Technology, Myongji University, Myongji-Ro 116, Cheoin-Gu, Yongin, Gyeonggi-Do 17058, Korea
,
a   School of Pharmacy, East China University of Science and Technology, Meilong Road 130, Shanghai 200237, P. R. of China
b   Department of Energy Science and Technology, Myongji University, Myongji-Ro 116, Cheoin-Gu, Yongin, Gyeonggi-Do 17058, Korea
c   Department of Chemistry, Myongji University, Myongji-Ro 116, Cheoin-Gu, Yongin, Gyeonggi-Do 17058, Korea   Email: sangkoo@mju.ac.kr
› Author Affiliations
This work was supported by 2018 Research Fund of Myongji University.
Further Information

Publication History

Received: 13 March 2019

Accepted after revision: 07 May 2019

Publication Date:
28 May 2019 (online)


These authors contributed equally to this work.

Abstract

Efficient synthetic method for medicinally and opto-electronically important bichalcophenes is reported, which highlights Mn(OAc)3/CoCl2-catalyzed oxidative deacetylation of 1,5-dicarbonyl compounds that were easily prepared by conjugate addition of ethyl acetoacetate to α,β-unsaturated carbonyl compounds containing a chalcophene unit. Paal–Knorr reaction of the resulting 1,4-dicarbonyl compounds produced 4-phenyl-2,2′-bichalcophenes and their aza-analogues.

Supporting Information