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Synthesis 2022; 54(20): 4583-4591
DOI: 10.1055/a-1844-5837
paper

Assembly of Pyran-Fused Isoquinolines via Rhodium-Catalyzed Double Annulations of Methyl Benzimidates with Diazo Compounds

Yinsong Wu‡
a   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. of China
,
Enshen Zhang‡
a   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. of China
,
Jiahui Duan
a   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. of China
,
Keke Xu
a   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. of China
,
Xinwei He  ∗
a   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. of China
b   Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province, Hunan Normal University, Changsha 410081, P. R. of China
,
Yongjia Shang∗
a   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. of China
› Author AffiliationsWe thank the National Natural Science Foundation of China (21772001), the Anhui Provincial Natural Science Foundation (1808085MB41), Cultivation Project for University Outstanding Talents of Anhui Province (2019), the University Synergy Innovation Program of Anhui Province (GXXT-2020-074), and Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province (KLOFMAA2020-04) for financial support.
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Abstract

A variety of pyran-fused isoquinoline derivatives were prepared in moderate to good yields through the rhodium-catalyzed dual C–H functionalization/annulation of methyl benzimidates and diazo compounds. A one-pot procedure, broad substrate scope, diversified products, and mild reaction conditions make this transformation a powerful tool for the synthesis of fused heteroarenes. In addition, the synthetic application was extended by large-scale synthesis and late-stage functionalization via Pd-catalyzed Suzuki–Miyaura, Heck, and Sonogashira cross-coupling reactions. Furthermore, a photophysical survey reveals that the pyran-fused isoquinoline products exhibit fluorescence properties and show potential for exploring fluorescent material applications.

Key words

annulations - C–H activation - diazo compounds - isoquinolines - methyl benzimidates

Supporting Information



Publication History

Received: 10 April 2022

Accepted after revision: 05 May 2022

Accepted Manuscript online:
05 May 2022

Article published online:
28 June 2022

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