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

Xia Jiang; Hui Jin; Tingshu Wang; Hyebin Yoo; Sangho Koo

doi:10.1055/s-0037-1611564

Synthesis, Inhaltsverzeichnis

Synthesis 2019; 51(17): 3259-3268
DOI: 10.1055/s-0037-1611564

paper

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

Xia Jiang

^aSchool of Pharmacy, East China University of Science and Technology, Meilong Road 130, Shanghai 200237, P. R. of China

^bDepartment of Energy Science and Technology, Myongji University, Myongji-Ro 116, Cheoin-Gu, Yongin, Gyeonggi-Do 17058, Korea

,

Hui Jin

^aSchool of Pharmacy, East China University of Science and Technology, Meilong Road 130, Shanghai 200237, P. R. of China

^bDepartment of Energy Science and Technology, Myongji University, Myongji-Ro 116, Cheoin-Gu, Yongin, Gyeonggi-Do 17058, Korea

,

Tingshu Wang

^aSchool of Pharmacy, East China University of Science and Technology, Meilong Road 130, Shanghai 200237, P. R. of China

^bDepartment of Energy Science and Technology, Myongji University, Myongji-Ro 116, Cheoin-Gu, Yongin, Gyeonggi-Do 17058, Korea

,

Hyebin Yoo

^bDepartment of Energy Science and Technology, Myongji University, Myongji-Ro 116, Cheoin-Gu, Yongin, Gyeonggi-Do 17058, Korea

,

Sangho Koo *

^aSchool of Pharmacy, East China University of Science and Technology, Meilong Road 130, Shanghai 200237, P. R. of China

^bDepartment of Energy Science and Technology, Myongji University, Myongji-Ro 116, Cheoin-Gu, Yongin, Gyeonggi-Do 17058, Korea

^cDepartment of Chemistry, Myongji University, Myongji-Ro 116, Cheoin-Gu, Yongin, Gyeonggi-Do 17058, Korea eMail: sangkoo@mju.ac.kr

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Abstract

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^† 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.

Key words

bichalcophene - catalytic oxidation - deacetylation - 1,4-dicarbonyl compound - Paal–Knorr reaction

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