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Cascade Lactonization/Benzannulation of Propargylamines with Dimethyl 3-Oxoglutarate for Modular Assembly of Hydroxylated/Arene-Functionalized Benzo[c]chromen-6-ones.
Duan, Jiahui; He, Xinwei; Choy, Pui Ying; Wang, Qi; Xie, Mengqing; Li, Ruxue; Xu, KeKe; Shang, Yongjia; Kwong, Fuk Yee.
Afiliação
  • Duan J; Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base), College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, P.R. China.
  • He X; Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base), College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, P.R. China.
  • Choy PY; State Key Laboratory of Synthetic Chemistry and Department of Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong, P.R. China.
  • Wang Q; Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base), College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, P.R. China.
  • Xie M; Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base), College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, P.R. China.
  • Li R; Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base), College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, P.R. China.
  • Xu K; Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base), College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, P.R. China.
  • Shang Y; Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base), College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, P.R. China.
  • Kwong FY; State Key Laboratory of Synthetic Chemistry and Department of Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong, P.R. China.
Org Lett ; 23(16): 6455-6460, 2021 08 20.
Article em En | MEDLINE | ID: mdl-34342448
ABSTRACT
A DBU-mediated cascade strategy of propargylamines with dimethyl 3-oxoglutarate for constructing a functionalized benzo[c]chromen-6-one core has been achieved. This cascade process presumably involves a sequence of 1,4-conjugate addition, followed by lactonization, alkyne-allene isomerization, enol-keto tautomerization, 6π-electrocyclization, and aromatization. This protocol features mild reaction conditions, simple operation, rich structural diversity, and good functional group tolerance. A photophysical survey reveals that the benzo[c]chromen-6-one products exhibit fluorescence properties and show potential for exploring fluorescent material applications.
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Texto completo: 1 Base de dados: MEDLINE Idioma: En Ano de publicação: 2021 Tipo de documento: Article
Texto completo
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Texto completo: 1 Base de dados: MEDLINE Idioma: En Ano de publicação: 2021 Tipo de documento: Article