CN115197143A - Dinaphthoazepine, derivative thereof and nickel catalytic synthesis method thereof - Google Patents

Dinaphthoazepine, derivative thereof and nickel catalytic synthesis method thereof Download PDF

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CN115197143A
CN115197143A CN202210580310.XA CN202210580310A CN115197143A CN 115197143 A CN115197143 A CN 115197143A CN 202210580310 A CN202210580310 A CN 202210580310A CN 115197143 A CN115197143 A CN 115197143A
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phenanthroline
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dimethylformamide
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CN115197143B (en
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邱仁华
张德奖
徐芝
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Hunan University
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
    • C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
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    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
    • B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
    • B01J31/1825—Ligands comprising condensed ring systems, e.g. acridine, carbazole
    • B01J31/183—Ligands comprising condensed ring systems, e.g. acridine, carbazole with more than one complexing nitrogen atom, e.g. phenanthroline
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    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
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    • C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
    • C07D491/14—Ortho-condensed systems
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    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/84—Metals of the iron group
    • B01J2531/847—Nickel
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Abstract

The invention discloses a kind of dinaphthoazepines and their derivatives and their nickel catalytic synthesis method. The method takes a dinaphthalene compound as a raw material, nickel bromide as a catalyst, 2,9-tetramethyl-1,10-phenanthroline as a ligand, lithium iodide as an additive, manganese powder as a reducing agent and N, N-dimethylformamide as a solvent, and a series of dinaphthylazepines are synthesized by reaction at 120 ℃. The reaction has good functional group tolerance and moderate to excellent yields.

Description

Dinaphthoazepine and its derivative and nickel catalytic synthesis method
Technical Field
The invention belongs to the field of catalytic organic synthesis, and particularly relates to a class of dinaphthylazepines and derivatives thereof as well as a nickel catalytic synthesis method thereof.
Background
The dinaphthyl secondary amine compound and the derivatives thereof play important roles in the aspects of pharmaceutical application and the field of organic catalysis, and the substances play roles as ligands or catalysts in a plurality of reactions of chiral transfer. There is great potential for the development of binaphthyl secondary amine compounds, but there are great challenges facing their efficient synthesis. Generally, a commercially available optical pure 1,1' -bis-2-naphthol is used as a basic chiral unit to design a symmetric synthetic chiral phase transfer catalyst, but the defects of long steps, harsh conditions and the like exist. Based on this, how to develop a high-efficiency synthesis method of the dinaphthoazepines compound is one of important research contents in the field of synthetic chemistry.
The construction of carbon-carbon bonds is a central topic of synthetic organic chemistry, as it is of great interest for the synthesis of a variety of structurally important molecules (including biological entities or natural products) from structurally simple and readily available molecules. The formation of carbon-carbon bonds has long been the subject of research of interest to scientists, and numerous strategies to address this problem have been developed. The past research on carbon-carbon bond construction has focused mainly on the utilization of alkali metal-containing organometallic compounds, and the last decade has witnessed a great advance in transition metal-catalyzed cross-coupling strategies, in which in-situ direct reductive coupling of halogenated aryl compounds (without the need for prior preparation of organometallic reagents) is one of the most convenient and rapid methods for preparing biaryls. In recent years, nickel catalytic reduction coupling reaction has rapidly progressed in synthesis, application and mechanism research. The reaction conditions are mild, and the advantages can be provided for the traditional cross-coupling reaction. For example, reductive coupling reactions do not require the preparation of organometallic reagents in advance, providing an attractive strategy for intramolecular cyclization reactions. Thus, we would like to be able to synthesize dinaphthoazepines and their derivatives by this strategy.
Disclosure of Invention
The invention discloses a dinaphthylazepine and a derivative thereof and a nickel catalytic synthesis method thereof, the method takes a dinaphthylamine compound as a raw material, nickel bromide as a catalyst, 2,9-dimethyl-1,10-phenanthroline as a ligand, lithium iodide as an additive, manganese powder as a reducing agent and N, N-dimethylformamide as a solvent, and a series of dinaphthylazepines are synthesized by reaction at 120 ℃. The scheme has the advantages of mild conditions, wide substrate range, good functional group tolerance, high yield, easy operation and the like, and lays a foundation for synthesizing the functionalized dinaphthoazepines.
In order to achieve the above purpose, the invention provides the following technical scheme:
a kind of dinaphthoazepinene and its derivative and its nickel catalytic synthesis method, wherein the product structural formula is as follows:
Figure RE-GDA0003844951590000021
the catalytic synthesis method of the dinaphthylazepine is characterized in that dibromonaphthylamine 1 (0.2 mmol) is used as a raw material, nickel bromide (10 mol%) is used as a catalyst, 2,9-tetramethyl-1,10-phenanthroline is used as a ligand, 2.0 equivalent of lithium iodide is used as an additive, 2.0 equivalent of manganese powder is used as a reducing agent, N, N-dimethylformamide is used as a solvent, the reaction is carried out for 12 hours at 120 ℃ in a nitrogen atmosphere to obtain dinaphthylazepine compounds 7a-7t, and the yield is 68-94%.
Drawings
FIG. 1 is a schematic diagram of the reaction principle and the products and yields of the present invention.
Detailed Description
The present invention will be described in detail with reference to the following embodiments in order to make the above features, advantages and objects of the invention more comprehensible. In the above description, numerous specific details are set forth in order to provide a thorough understanding of the present invention. This invention may, however, be embodied in many different forms than those specifically described herein, and it will be apparent to those skilled in the art that many more modifications are possible without departing from the spirit and scope of the invention.
The reaction materials and catalysts mentioned in the following examples are commercially available reagents which are conventional in the market, unless otherwise specified.
Preparation of dibenzo [ c, e ] azepines examples 1-20
Example 1
Adding 10.2mmol of dibromonaphthylamine, 0.02mmol of nickel bromide, 0.02mmol of 2, 9-dimethyl-1,10-phenanthroline, 0.4mmol of lithium iodide, 0.4mmol of manganese powder, 2.0mL of N, N-dimethylformamide as a solvent into a 10mL reaction tube, and reacting for 12 hours at 120 ℃ in a nitrogen atmosphere. After the reaction was completed, the compound 7a was isolated by column chromatography as a white solid with a yield of 92%.
Example 2
Adding 10.2mmol of dibromonaphthylamine, 0.02mmol of nickel bromide, 0.02mmol of 2, 9-dimethyl-1,10-phenanthroline, 0.4mmol of lithium iodide, 0.4mmol of manganese powder, 2.0mL of N, N-dimethylformamide as a solvent into a 10mL reaction tube, and reacting for 12 hours at 120 ℃ in a nitrogen atmosphere. After the reaction was completed, the compound 7b was isolated by column chromatography as a white solid with a yield of 94%.
Example 3
Adding 10.2mmol of dibromonaphthylamine, 0.02mmol of nickel bromide, 0.02mmol of 2, 9-dimethyl-1,10-phenanthroline, 0.4mmol of lithium iodide, 0.4mmol of manganese powder, 2.0mL of N, N-dimethylformamide as a solvent into a 10mL reaction tube, and reacting for 12 hours at 120 ℃ in a nitrogen atmosphere. After the reaction, the dibenzo [ c, e ] heptine compound 7c was obtained as a white solid by column chromatography with a yield of 90%.
Example 4
Adding 10.2mmol of dibromonaphthylamine, 0.02mmol of nickel bromide, 0.02mmol of 2, 9-dimethyl-1,10-phenanthroline, 0.4mmol of lithium iodide, 0.4mmol of manganese powder, 2.0mL of N, N-dimethylformamide as a solvent into a 10mL reaction tube, and reacting for 12 hours at 120 ℃ in a nitrogen atmosphere. After the reaction was completed, the compound 7d was isolated by column chromatography as a white solid with a yield of 89%.
Example 5
Adding 10.2mmol of dibromonaphthylamine, 0.02mmol of nickel bromide, 0.02mmol of 2, 9-dimethyl-1,10-phenanthroline, 0.4mmol of lithium iodide, 0.4mmol of manganese powder, 2.0mL of N, N-dimethylformamide as a solvent into a 10mL reaction tube, and reacting for 12 hours at 120 ℃ in a nitrogen atmosphere. After the reaction was completed, the compound 7e was isolated by column chromatography as a white solid with a yield of 92%.
Example 6
Adding 10.2mmol of dibromonaphthylamine, 0.02mmol of nickel bromide, 0.02mmol of 2, 9-dimethyl-1,10-phenanthroline, 0.4mmol of lithium iodide, 0.4mmol of manganese powder, 2.0mL of N, N-dimethylformamide as a solvent into a 10mL reaction tube, and reacting for 12 hours at 120 ℃ in a nitrogen atmosphere. After the reaction was completed, the compound 7f of dinaphthylazepine was isolated by column chromatography as a white solid with a yield of 93%.
Example 7
Adding 10.2mmol of dibromonaphthylamine, 0.02mmol of nickel bromide, 0.02mmol of 2, 9-dimethyl-1,10-phenanthroline, 0.4mmol of lithium iodide, 0.4mmol of manganese powder, 2.0mL of N, N-dimethylformamide as a solvent into a 10mL reaction tube, and reacting for 12 hours at 120 ℃ in a nitrogen atmosphere. After the reaction was completed, 7g of the dinaphthylazepine compound was obtained as a white solid by column chromatography with a yield of 88%.
Example 8
Adding 10.2mmol of dibromonaphthylamine, 0.02mmol of nickel bromide, 0.02mmol of 2, 9-dimethyl-1,10-phenanthroline, 0.4mmol of lithium iodide, 0.4mmol of manganese powder, and 2.0mL of N, N-dimethylformamide into a 10mL reaction tube, and reacting for 12 hours at 120 ℃ in a nitrogen atmosphere. After the reaction was completed, the compound dinaphthoazepine was obtained by column chromatography for 7 hours as a white solid with a yield of 89%.
Example 9
Adding 10.2mmol of dibromonaphthylamine, 0.02mmol of nickel bromide, 0.02mmol of 2, 9-dimethyl-1,10-phenanthroline, 0.4mmol of lithium iodide, 0.4mmol of manganese powder, 2.0mL of N, N-dimethylformamide as a solvent into a 10mL reaction tube, and reacting for 12 hours at 120 ℃ in a nitrogen atmosphere. After the reaction was completed, the compound 7i of dinaphthylazepine was obtained as a white solid by column chromatography in 84% yield.
Example 10
Adding 10.2mmol of dibromonaphthylamine, 0.02mmol of nickel bromide, 0.02mmol of 2, 9-dimethyl-1,10-phenanthroline, 0.4mmol of lithium iodide, 0.4mmol of manganese powder, and 2.0mL of N, N-dimethylformamide into a 10mL reaction tube, and reacting for 12 hours at 120 ℃ in a nitrogen atmosphere. After the reaction was completed, the compound 7j was isolated by column chromatography as a white solid with a yield of 84%.
Example 11
Adding 10.2mmol of dibromonaphthylamine, 0.02mmol of nickel bromide, 0.02mmol of 2, 9-dimethyl-1,10-phenanthroline, 0.4mmol of lithium iodide, 0.4mmol of manganese powder, 2.0mL of N, N-dimethylformamide as a solvent into a 10mL reaction tube, and reacting for 12 hours at 120 ℃ in a nitrogen atmosphere. After the reaction was completed, the compound 7k was isolated by column chromatography as a white solid with a yield of 93%.
Example 12
Adding 10.2mmol of dibromonaphthylamine, 0.02mmol of nickel bromide, 0.02mmol of 2, 9-dimethyl-1,10-phenanthroline, 0.4mmol of lithium iodide, 0.4mmol of manganese powder, 2.0mL of N, N-dimethylformamide as a solvent into a 10mL reaction tube, and reacting for 12 hours at 120 ℃ in a nitrogen atmosphere. After the reaction was completed, 7l of the dinaphthylazepine compound was obtained as a white solid by column chromatography with a yield of 92%.
Example 13
Adding 10.2mmol of dibromonaphthylamine, 0.02mmol of nickel bromide, 0.02mmol of 2, 9-dimethyl-1,10-phenanthroline, 0.4mmol of lithium iodide, 0.4mmol of manganese powder, 2.0mL of N, N-dimethylformamide as a solvent into a 10mL reaction tube, and reacting for 12 hours at 120 ℃ in a nitrogen atmosphere. After the reaction was completed, the compound 7m was isolated by column chromatography as a white solid with a yield of 89%.
Example 14
Adding 10.2mmol of dibromonaphthylamine, 0.02mmol of nickel bromide, 0.02mmol of 2, 9-dimethyl-1,10-phenanthroline, 0.4mmol of lithium iodide, 0.4mmol of manganese powder, 2.0mL of N, N-dimethylformamide as a solvent into a 10mL reaction tube, and reacting for 12 hours at 120 ℃ in a nitrogen atmosphere. After the reaction was completed, the compound 7n was isolated by column chromatography to give a white solid with a yield of 91%.
Example 15
Adding 10.2mmol of dibromonaphthylamine, 0.02mmol of nickel bromide, 0.02mmol of 2, 9-dimethyl-1,10-phenanthroline, 0.4mmol of lithium iodide, 0.4mmol of manganese powder, 2.0mL of N, N-dimethylformamide as a solvent into a 10mL reaction tube, and reacting for 12 hours at 120 ℃ in a nitrogen atmosphere. After the reaction was completed, the compound 7o was obtained as a colorless liquid by column chromatography separation, and the yield was 90%.
Example 16
Adding 10.2mmol of dibromonaphthylamine, 0.02mmol of nickel bromide, 0.02mmol of 2, 9-dimethyl-1,10-phenanthroline, 0.4mmol of lithium iodide, 0.4mmol of manganese powder, 2.0mL of N, N-dimethylformamide as a solvent into a 10mL reaction tube, and reacting for 12 hours at 120 ℃ in a nitrogen atmosphere. After the reaction was completed, the compound 7p was isolated by column chromatography as a white solid with a yield of 87%.
Example 17
Adding 10.2mmol of dibromonaphthylamine, 0.02mmol of nickel bromide, 0.02mmol of 2, 9-dimethyl-1,10-phenanthroline, 0.4mmol of lithium iodide, 0.4mmol of manganese powder, 2.0mL of N, N-dimethylformamide as a solvent into a 10mL reaction tube, and reacting for 12 hours at 120 ℃ in a nitrogen atmosphere. After the reaction was completed, the compound 7q was isolated by column chromatography as a colorless liquid in a yield of 68%.
Example 18
Adding 10.2mmol of dibromonaphthylamine, 0.02mmol of nickel bromide, 0.02mmol of 2, 9-dimethyl-1,10-phenanthroline, 0.4mmol of lithium iodide, 0.4mmol of manganese powder, 2.0mL of N, N-dimethylformamide as a solvent into a 10mL reaction tube, and reacting for 12 hours at 120 ℃ in a nitrogen atmosphere. After the reaction was completed, the compound 7r was isolated by column chromatography as a colorless liquid with a yield of 82%.
Example 19
Adding 10.2mmol of dibromonaphthylamine, 0.02mmol of nickel bromide, 0.02mmol of 2, 9-dimethyl-1,10-phenanthroline, 0.4mmol of lithium iodide, 0.4mmol of manganese powder, 2.0mL of N, N-dimethylformamide as a solvent into a 10mL reaction tube, and reacting for 12 hours at 120 ℃ in a nitrogen atmosphere. After the reaction was completed, the compound 7s of dinaphthylazepine was isolated by column chromatography as a white solid with a yield of 86%.
Example 20
Adding 10.2mmol of dibromonaphthylamine, 0.02mmol of nickel bromide, 0.02mmol of 2, 9-dimethyl-1,10-phenanthroline, 0.4mmol of lithium iodide, 0.4mmol of manganese powder, 2.0mL of N, N-dimethylformamide as a solvent into a 10mL reaction tube, and reacting for 12 hours at 120 ℃ in a nitrogen atmosphere. After the reaction was completed, the compound 7t of dinaphthoazepine was obtained as a white solid by column chromatography with a yield of 86%.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the present invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent should be defined by the appended claims.

Claims (2)

1. A kind of dinaphthylazepines and its derivatives 7 and its nickel catalytic synthesis method, in which the structural formula and yield of the product 7 are as follows:
Figure FDA0003663520810000011
2. the application of claim 1, wherein dibromonaniline compound 6 (0.2 mmol) is used as raw material, nickel bromide (10 mol%) is used as catalyst, 2,9-dimethyl-1,10-phenanthroline (10 mol%) is used as ligand, 2.0 equivalent of lithium iodide is used as additive, 2.0 equivalent of manganese powder is used as reducing agent, N, N-dimethylformamide is used as solvent, and the reaction is carried out at 120 ℃ for 12 hours under nitrogen atmosphere to obtain dinaphthylazepine compound 7a-7t, and the yield is 68-94%.
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