Cp*Rh(<scp>iii</scp>)-catalyzed regioselective cyclization of aromatic amides with allenes

Liu, Jing; Liu, Deng-Yin; Yang, Qian; Zeng, Yao-Fu; Wang, Xiao-Li; Wang, Peng-Fei; Ruan, Yu-Jun; Wen, Miao-Miao; Zhang, Shang-Shi; Du, Li-da; Liu, Xu-Ge

doi:10.1039/d3cc05342c

Chem. Commun.

2024

DOI: 10.1039/d3cc05342c

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Cp*Rh(iii)-catalyzed regioselective cyclization of aromatic amides with allenes

Jing Liu,

Deng-Yin Liu,

Qian Yang

et al.

Abstract: A mild reaction condition is employed for the Cp*Rh(iii)-catalyzed regioselective annulation of aromatic amides with allenes, enabling the preparation of isoquinolin-1(2H)-ones and pyrimido[1,6-a]indol-1(2H)-one.

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Cited by 4 publications

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Cp*Rh(III)‐Catalyzed Divergent Synthesis of N‐Heterocycles with N‐Methoxyindoleamides and Isoxazolones

Shen,

Zou,

Chen

et al. 2024

Adv Synth Catal

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A method for synthesizing pyrimido[1,2‐a]indol‐4‐ol heteroarenes via a Cp*Rh(III)‐catalyzed cascade C‐H activation/annulation strategy employing N‐methoxyindoleamides and isoxazolones is developed. Also, a framework of 3‐methoxy‐2,3‐dihydro‐[1,3,5]triazino[1,2‐a]indole‐4,10‐dione was successfully synthesized via a Cp*Rh‐catalyzed C‐H activation/annulation/oxidation reaction between N‐(methyloxy)‐1H‐indole‐1‐carboxamide and isoxazolones. These reactions demonstrated the suitability of several substrates, compatibility with numerous functional groups, and mild reaction conditions. Preliminary mechanistic investigations have been completed.

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Cp*Rh(III)‐Catalyzed Divergent Synthesis of N‐Heterocycles with N‐Methoxyindoleamides and Isoxazolones

Shen,

Zou,

Chen

et al. 2024

Adv Synth Catal

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Rh(III)‐Catalyzed Annulation of (Het)aryl Amides with α‐Allenyl‐Containing α‐Amino Acid Derivatives

Vorobyeva,

Bubnova,

Godovikov

et al. 2024

Asian J Org Chem

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An efficient pathway to a new series of CF3‐substituted α‐amino acid derivatives decorated with pharmacophore isoquinolone and pyrimido[1,6‐a]indolone cores has been developed. The method includes Rh(III)‐catalyzed C‐H activation/[4+2]‐annulation of N‐(pivaloyloxy)‐substituted aryl hydroxamates and indole‐1‐carboxamides with readily available allenyl‐containing α‐amino carboxylates and their phosphorus analogues. It was established that the reactions occur via Rh‐σ‐alkenyl intermediates to provide new C‐C bond forming process with the participation of terminal carbon atom of allene moiety.

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Assembly of Heterocyclic C-Glycosides by Ru-Catalyzed C–H Activation/Cyclization with Carbonyl Sulfoxonium Ylide Glyco-Reagents

Liu,

Wang,

Ruan

et al. 2024

Org. Lett.

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New carbonyl sulfoxonium ylide glyco-reagents have been developed, enabling the synthesis of versatile heteroarene C-glycosides through a Ru-catalyzed C−H activation/annulation strategy. These reactions tolerate various saccharide donors and represent a significant advance in the stereoselective synthesis of heterocyclic C-glycosides. Furthermore, the strategy and methods could be applied to large-scale reactions and late-stage modifications of some structurally complex natural products or drugs.

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Cp*Rh(iii)-catalyzed regioselective cyclization of aromatic amides with allenes

Abstract: A mild reaction condition is employed for the Cp*Rh(iii)-catalyzed regioselective annulation of aromatic amides with allenes, enabling the preparation of isoquinolin-1(2H)-ones and pyrimido[1,6-a]indol-1(2H)-one.

Cited by 4 publications

References 50 publications

Cp*Rh(III)‐Catalyzed Divergent Synthesis of N‐Heterocycles with N‐Methoxyindoleamides and Isoxazolones

Cp*Rh(III)‐Catalyzed Divergent Synthesis of N‐Heterocycles with N‐Methoxyindoleamides and Isoxazolones

Rh(III)‐Catalyzed Annulation of (Het)aryl Amides with α‐Allenyl‐Containing α‐Amino Acid Derivatives

Assembly of Heterocyclic C-Glycosides by Ru-Catalyzed C–H Activation/Cyclization with Carbonyl Sulfoxonium Ylide Glyco-Reagents

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