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

Yinsong Wu; Enshen Zhang; Jiahui Duan; Keke Xu; Xinwei He; Yongjia Shang

doi:10.1055/a-1844-5837

Synthesis, Table of Contents

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

Authors

Yinsong Wu‡

^aKey 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‡

^aKey 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

^aKey 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

^aKey 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 ∗

^aKey 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

^bKey Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province, Hunan Normal University, Changsha 410081, P. R. of China
Yongjia Shang∗

^aKey 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

Abstract

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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

Full Text

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Supplementary Material