Copper-Catalyzed Synthesis of Dibenzo[b,f]imidazo[1,2-d][1,4]oxazepine Derivatives via a Double Ullmann Coupling Reaction

Chen, Xinyi; Li, Zhuo-Huan; Liu, Jianquan; Wang, Xiang‐Shan

doi:10.1055/s-0037-1611945

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Cited by 9 publications

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Convenient Assembly of Privileged (Hetero)Arene‐Fused Benzo[1.4]oxazepines via Two Tandem S_NAr Events. Part 3 – (Hetero)arene‐Fused benzo[f]imidazo[1,2‐d][1,4]oxazepines

et al. 2020

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A tandem approach to (hetero)arene‐fused benzo[f]imidazo[1,2‐d][1,4]oxazepines has been described which involves condensation of bis‐nucleophilic 2‐(2‐hydrohyaryl)imidazoles with reactivity‐matched o‐dihalo and o‐halonitro (hetero)aromatic substrates. The process is generally regioselective with respect to the unsymmetrically substituted imidazole ring and proceeds via two SNAr events (intermolecular first and then intramolecular) intermitted by a Smiles rearrangement. In some cases, the last SNAr step provides a rare example of nucleophilic displacement of a nitro group or a halogen in non‐activated positions of a (hetero)aromatic ring which does not require the use of a metal catalyst.

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Convenient Assembly of Privileged (Hetero)Arene‐Fused Benzo[1.4]oxazepines via Two Tandem S_NAr Events. Part 3 – (Hetero)arene‐Fused benzo[f]imidazo[1,2‐d][1,4]oxazepines

et al. 2020

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Five-membered ring systems: with more than one N atom

Yet

2021

Progress in Heterocyclic Chemistry

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Seven-membered rings

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et al. 2021

Progress in Heterocyclic Chemistry

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Copper-Catalyzed Synthesis of Dibenzo[b,f]imidazo[1,2-d][1,4]oxazepine Derivatives via a Double Ullmann Coupling Reaction

Cited by 9 publications

References 5 publications

Convenient Assembly of Privileged (Hetero)Arene‐Fused Benzo[1.4]oxazepines via Two Tandem S_NAr Events. Part 3 – (Hetero)arene‐Fused benzo[f]imidazo[1,2‐d][1,4]oxazepines

Convenient Assembly of Privileged (Hetero)Arene‐Fused Benzo[1.4]oxazepines via Two Tandem S_NAr Events. Part 3 – (Hetero)arene‐Fused benzo[f]imidazo[1,2‐d][1,4]oxazepines

Five-membered ring systems: with more than one N atom

Seven-membered rings

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Copper-Catalyzed Synthesis of Dibenzo[b,f]imidazo[1,2-d][1,4]oxazepine Derivatives via a Double Ullmann Coupling Reaction

Cited by 9 publications

References 5 publications

Convenient Assembly of Privileged (Hetero)Arene‐Fused Benzo[1.4]oxazepines via Two Tandem SNAr Events. Part 3 – (Hetero)arene‐Fused benzo[f]imidazo[1,2‐d][1,4]oxazepines

Convenient Assembly of Privileged (Hetero)Arene‐Fused Benzo[1.4]oxazepines via Two Tandem SNAr Events. Part 3 – (Hetero)arene‐Fused benzo[f]imidazo[1,2‐d][1,4]oxazepines

Five-membered ring systems: with more than one N atom

Seven-membered rings

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Product

Resources

About

Convenient Assembly of Privileged (Hetero)Arene‐Fused Benzo[1.4]oxazepines via Two Tandem S_NAr Events. Part 3 – (Hetero)arene‐Fused benzo[f]imidazo[1,2‐d][1,4]oxazepines

Convenient Assembly of Privileged (Hetero)Arene‐Fused Benzo[1.4]oxazepines via Two Tandem S_NAr Events. Part 3 – (Hetero)arene‐Fused benzo[f]imidazo[1,2‐d][1,4]oxazepines