Cu-Catalyzed synthesis of spiroimidazole derivatives <i>via</i> an indolyl mediated cyclization–rearrangement reaction

Chen, Shanping; Yi, Xin; Wei, Feng; You, Kuiyi; Mao, Guojiang; Deng, Guo‐Jun

doi:10.1039/d2qo01237e

Org. Chem. Front.

2022

DOI: 10.1039/d2qo01237e

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Cu-Catalyzed synthesis of spiroimidazole derivatives via an indolyl mediated cyclization–rearrangement reaction

Shanping Chen

Xin Yi

Feng Wei

et al.

Abstract: A novel Cu-catalyzed synthesis of structurally valuable spiro imidazole derivatives from 2-(indol-3-yl)cyclohexanones and amidines via indolyl mediated cyclization-rearrangement reaction is described. The present approach features advantages including easily available starting...

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Cited by 3 publications

References 45 publications

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Metal- and Solvent-Free Synthesis of Substituted Pyrimidines via an NH₄I-Promoted Three-Component Tandem Reaction

Fang,

Xia,

Quan

et al. 2023

J. Org. Chem.

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A facile and practical approach for the preparation of substituted pyrimidines from ketones, NH 4 OAc, and N,N-dimethylformamide dimethyl acetal has been described. This NH 4 I-promoted three-component tandem reaction affords a broad range of substituted pyrimidines in acceptable yields under metal-and solvent-free conditions. The present methodology features the advantages of simple and easily available starting materials, metaland solvent-free conditions, a broad substrate scope with good functional group tolerance, and gram-scale synthesis.

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Metal- and Solvent-Free Synthesis of Substituted Pyrimidines via an NH₄I-Promoted Three-Component Tandem Reaction

Fang,

Xia,

Quan

et al. 2023

J. Org. Chem.

Self Cite

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Base-Promoted Tandem Cyclization of 2-(Indol-3-yl)naphthoquinones with Benzamidines toward Polysubstituted Pyrimido[4,5-b]indoles

Tan,

Hu,

Zhang

et al. 2024

Org. Lett.

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A novel and unique approach for the construction of polysubstituted pyrimido [4,5-b]indoles from 2-(indol-3-yl)naphthoquinones and benzamidines is described. Our strategy, promoted by an inorganic base, involves the ring opening and recyclization of naphthoquinone and produces three nitrogen heterocyclic rings via multiple C−N bond formations in one pot under transition-metal-free conditions.P yrimido[4,5-b]indoles represent a privileged type of nitrogen-containing heterocycles, which are widespread in a diverse range of natural products and pharmaceutically active molecules. 1,2 Pyrimido[4,5-b]indole derivatives have extensive biological activities, including antiinflammatory, antibacterial, antimalarial, antihypertensive, anticancer, and antiasthmatic activities. 3,4 Pyrimidoindoles can also be used as cytotoxic inhibitors and kinase inhibitors. 5 Additionally, some pyrimido [4,5-b]indole derivatives have proven to be agonists of human hematopoietic stem cell self-renewal. 6 Several representative bioactive molecules containing a pyrimidoindole skeleton are shown in Figure 1.

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Base-promoted ring-opening/recyclization of naphthoquinones to access benzo[5,6][1,4]thiazino[4,3-b]isoquinoline-7,12-diones at room temperature

Tan,

Li,

Zhou

et al. 2024

Org. Chem. Front.

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Cu-Catalyzed synthesis of spiroimidazole derivatives via an indolyl mediated cyclization–rearrangement reaction

Abstract: A novel Cu-catalyzed synthesis of structurally valuable spiro imidazole derivatives from 2-(indol-3-yl)cyclohexanones and amidines via indolyl mediated cyclization-rearrangement reaction is described. The present approach features advantages including easily available starting...

Cited by 3 publications

References 45 publications

Metal- and Solvent-Free Synthesis of Substituted Pyrimidines via an NH₄I-Promoted Three-Component Tandem Reaction

Metal- and Solvent-Free Synthesis of Substituted Pyrimidines via an NH₄I-Promoted Three-Component Tandem Reaction

Base-Promoted Tandem Cyclization of 2-(Indol-3-yl)naphthoquinones with Benzamidines toward Polysubstituted Pyrimido[4,5-b]indoles

Base-promoted ring-opening/recyclization of naphthoquinones to access benzo[5,6][1,4]thiazino[4,3-b]isoquinoline-7,12-diones at room temperature

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Cu-Catalyzed synthesis of spiroimidazole derivatives via an indolyl mediated cyclization–rearrangement reaction

Abstract: A novel Cu-catalyzed synthesis of structurally valuable spiro imidazole derivatives from 2-(indol-3-yl)cyclohexanones and amidines via indolyl mediated cyclization-rearrangement reaction is described. The present approach features advantages including easily available starting...

Cited by 3 publications

References 45 publications

Metal- and Solvent-Free Synthesis of Substituted Pyrimidines via an NH4I-Promoted Three-Component Tandem Reaction

Metal- and Solvent-Free Synthesis of Substituted Pyrimidines via an NH4I-Promoted Three-Component Tandem Reaction

Base-Promoted Tandem Cyclization of 2-(Indol-3-yl)naphthoquinones with Benzamidines toward Polysubstituted Pyrimido[4,5-b]indoles

Base-promoted ring-opening/recyclization of naphthoquinones to access benzo[5,6][1,4]thiazino[4,3-b]isoquinoline-7,12-diones at room temperature

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Product

Resources

About

Metal- and Solvent-Free Synthesis of Substituted Pyrimidines via an NH₄I-Promoted Three-Component Tandem Reaction

Metal- and Solvent-Free Synthesis of Substituted Pyrimidines via an NH₄I-Promoted Three-Component Tandem Reaction