Synthesis of 4-oxo-5-(arylformyl acetate-2-yl)naphthalene-sulfoxide ylide hybrids

A technology of arylformyl acetate and arylformyl sulfoxide, which is applied in the field of synthesis of 4-oxo-5-naphthalene-sulfoxide ylide hybrid, and achieves simple operation process, high atom economy, and scope of application wide effect

Active Publication Date: 2020-10-09
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although there are currently effective methods for the synthesis of 4-oxo-5-(arylformylacetate-2-yl)naphthalene or sulfoxide ylides, the construction of 4-oxo-5-(arylformylacetate-2-yl) 2-yl) naphthalene-sulfoxide ylide hybrids, that is, the method of multifunctional naphthalene derivatives with structural units such as α-aryl formyl acetate and sulfoxide ylide on the naphthalene ring has not yet been reported in the literature.

Method used

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  • Synthesis of 4-oxo-5-(arylformyl acetate-2-yl)naphthalene-sulfoxide ylide hybrids
  • Synthesis of 4-oxo-5-(arylformyl acetate-2-yl)naphthalene-sulfoxide ylide hybrids
  • Synthesis of 4-oxo-5-(arylformyl acetate-2-yl)naphthalene-sulfoxide ylide hybrids

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Experimental program
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Effect test

Embodiment 1

[0020]

[0021] 1a (0.5mmol, 98mg), 2a (0.5mmol, 109mg), silver hexafluoroantimonate (27.5mg, 0.08mmol), [RhCp*Cl 2 ] 2 (12mg, 0.02mmol) and 1,2-dichloroethane (3mL), stirred at 80°C for 24h under nitrogen atmosphere. TLC detects that in addition to the main product, there is also a major impurity point generated. Then the reaction system was cooled to room temperature, 10 mL of saturated brine was added to quench the reaction, extracted with ethyl acetate (10 mL×3), the organic phases were combined, and washed with anhydrous Na 2 SO 4 After drying, the solvent was spin-dried and separated by silica gel column (petroleum ether / ethyl acetate=1 / 1) to obtain the product 3a (64 mg, 23%) as a pale yellow solid. The characterization data of this compound are as follows: 1 H NMR (600MHz, CDCl 3 )δ: 0.80(t, J=7.2Hz, 3H), 1.17(t, J=7.2Hz, 3H), 3.56(s, 3H), 3.58(s, 3H), 3.81(q, J=7.2Hz, 2H), 4.17(q, J=7.2Hz, 2H), 7.08(d, J=7.2Hz, 1H), 7.24-7.32(m, 7H), 7.36-7.42(m, 2H), 7.54(d,...

Embodiment 2

[0023] 1a (0.5mmol, 98mg), 2a (0.5mmol, 109mg), silver hexafluoroantimonate (27.5mg, 0.08mmol), [RhCp*Cl 2 ] 2 (12mg, 0.02mmol) and tetrahydrofuran (3mL), stirred at 80°C for 24h under nitrogen atmosphere. TLC detects that in addition to the main product, there is also a major impurity point generated. Then the reaction system was cooled to room temperature, 10 mL of saturated brine was added to quench the reaction, extracted with ethyl acetate (10 mL×3), the organic phases were combined, and washed with anhydrous Na 2 SO 4 After drying, the solvent was spin-dried and separated by silica gel column (petroleum ether / ethyl acetate=1 / 1) to obtain product 3a (39 mg, 14%) as a pale yellow solid.

Embodiment 3

[0025] 1a (0.5mmol, 98mg), 2a (0.5mmol, 109mg), silver hexafluoroantimonate (27.5mg, 0.08mmol), [RhCp*Cl 2 ] 2 (12mg, 0.02mmol) and acetonitrile (3mL), stirred at 80°C for 24h under nitrogen atmosphere. TLC detects that in addition to the main product, there is also a major impurity point generated. Then the reaction system was cooled to room temperature, 10 mL of saturated brine was added to quench the reaction, extracted with ethyl acetate (10 mL×3), the organic phases were combined, and washed with anhydrous Na 2 SO 4 After drying, the solvent was spin-dried and separated by silica gel column (petroleum ether / ethyl acetate=1 / 1) to obtain product 3a (28 mg, 10%) as a pale yellow solid.

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Abstract

The invention discloses a method for synthesizing 4-oxo-5-(aroyl acetate-2-yl) naphthalene-sulfoxide ylide hybrid, and belongs to the technical field of organic synthesis. The synthesis method adopts arylformyl sulfoxide ylide 1 and α-diazocarbonyl compound 2 as raw materials, and in the presence of rhodium catalyst and silver hexafluoroantimonate additive, a series reaction is carried out to obtain 4-oxo-5-(arylmethyl) Acyl acetate-2-yl) naphthalene-sulfoxide ylide hybrid 3. Through the series reaction, the present invention has high atom economy; the operation process is simple and efficient; the reaction process does not require the participation of alkali or acid, and is more economical, green, and environmentally friendly; The synthesis of naphthalene-sulfoxide ylide hybrids provides an economical and practical new method.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for synthesizing 4-oxo-5-(aroyl acetate-2-yl)naphthalene-sulfoxide ylide hybrids. Background technique [0002] 4-Oxo-5-(aroylacetate-2-yl)naphthalene-sulfoxide ylide hybrids are an important class of functionalized naphthalene derivatives, which can be used for the high-efficiency synthesis of various drugs, fragrances and luminescent materials. preparation. At the same time, as an important intermediate in organic synthesis, sulfoxide ylides can be used in organic reactions such as cyclization, insertion and substitution, and have been widely used in the field of organic synthesis. [0003] However, the combination of 4-oxo-5-(arylformylacetate-2-yl)naphthalene and sulfoxide ylide is still a research blank, and it is expected that 4-oxo-5-(arylformylacetate-2-yl)naphthalene and sulfoxide ylide Ester-2-yl)naphthalene-sulfoxide ylide hybrids will ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C381/00C07D307/54
Inventor 范学森王慕华陈茜张新迎
Owner HENAN NORMAL UNIV
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