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Preparation method of phenazine compound

A compound, phenazine technology, applied in the field of preparation of phenazine compounds, can solve problems such as lower-than-expected development

Inactive Publication Date: 2021-09-24
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the development of facile synthetic routes starting from readily available starting materials has been far below expectations

Method used

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  • Preparation method of phenazine compound
  • Preparation method of phenazine compound
  • Preparation method of phenazine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-14

[0021] Examples 1-14 The reaction conditions optimization experiment

[0022] 1a of nitrosobenzene to p-type amino acid of formula 2a as the raw material, The effects of different reaction conditions on the catalytic yield of the target product 3aa, results as shown in Table 1, the following reaction formula:

[0023]

[0024] Table 1:

[0025]

[0026]

[0027] a Reaction conditions: 1a (0.1mmol), 2a (0.2mmol), solvent: (1.5mL), 140 ℃, under an air atmosphere in the reaction 16h, isolated yield. b PivOH (2equiv). c CF 3 SO 3 H (2equiv). d Solvent: ethyl acetate, e Solvent: dichloromethane, f The reaction under oxygen atmosphere 16h, g The reaction under a nitrogen atmosphere 16h, h 120 ℃, i 150 ℃. Wherein, TFE represents 2,2,2-trifluoroethanol.

[0028] Example 14 In an example, a typical test procedure is as follows:

[0029]

[0030] To 20mL Schlenk tube equipped with a magnetic stirring sealed reactor, were added successively p-amino-acid 1a (0.1mmol, 1.0equiv.), Nitro...

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Abstract

The invention discloses a silver-promoted cyclization reaction of an aryl carbamic acid compound and a nitroso aromatic compound. According to the method, a phenazine compound is prepared with medium to excellent yield through continuous ortho-position C-H functionalization, nitroso insertion and decarboxylation cyclization processes of aryl carbamic acid, and carboxyl amino is used as a traceless positioning group.

Description

Technical field [0001] The present application belongs to the technical field of organic synthesis, particularly relates to a method for preparing a compound of phenazine. Background technique [0002] Phenazine as an important structural units widely present in natural products, pharmaceutical compounds, agrochemicals, materials, and optical sensing chemical structure, therefore, synthetic organic chemists for the synthesis of such a skeleton structure constructed to give a sustained attention. In addition to the conventional synthetic route, the transition metal catalyzed reaction is a powerful tool for building such compounds, such as a continuous Buchwald-Hartwig amination prepared phenazine (J.Med.Chem.2018,61,3962; New J.Chem.2020, 44,3278; Chem.Commun.2020,56,2260).. Recently, Ellman's reported a rhodium catalyzed reaction of benzaldehyde and aromatic azides, for constructing phenazine skeleton (J.Am.Chem.Soc.2013,135,12548). Chen et al have developed between the copper ca...

Claims

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Application Information

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IPC IPC(8): C07D241/46
CPCC07D241/46
Inventor 成江王璐
Owner WENZHOU UNIVERSITY
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