Synthesis and application of naphthalenone-sulfoxide ylide hybrid

A technology of sulfoxide leaf and naphthalene ketone is applied in the synthesis and application field of naphthalene ketone-sulfoxide ylide hybrid, and achieves the effects of wide application range, good application prospect and high atom economy

Active Publication Date: 2019-05-10
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Combining naphthalene and sulfoxide ylide to form a new naphthone-sulfoxide ylide hybrid (that is, containing both naphthalene and sulfoxide ylide structural units in the same molecule), and using it as a key common intermediate , to complete the transformation of the above-mentioned functional group naphthalene derivatives has not yet been reported in public information

Method used

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  • Synthesis and application of naphthalenone-sulfoxide ylide hybrid
  • Synthesis and application of naphthalenone-sulfoxide ylide hybrid
  • Synthesis and application of naphthalenone-sulfoxide ylide hybrid

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Experimental program
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Effect test

Embodiment 1

[0032]

[0033] 1a (0.5mmol, 98mg), 2a (0.5mmol, 109mg), silver hexafluoroantimonate (27.5mg, 0.08mmol), [RhCp*Cl 2 ] 2 (12mg, 0.02mmol) and 2,2,2-trifluoroethanol (3mL), stirred at 80°C for 24h under nitrogen atmosphere. 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 (ethyl acetate / methanol=20 / 1) to obtain the product 3a (79 mg, 43%) as a white solid. The characterization data of this compound are as follows: 1 H NMR (400MHz, CDCl 3 )δ: 0.81(t, J=7.2Hz, 3H), 3.70(s, 6H), 3.84(q, J=7.2Hz, 2H), 7.24-7.28(m, 5H), 7.38(t, J=7.2 Hz,1H),7.53(t,J=7.6Hz,1H),7.63(dd,J 1 =8.4Hz,J 2 =0.8Hz,1H),8.32(d,J=8.0Hz,1H). 13C NMR (150MHz, CDCl 3 )δ: 13.7, 43.8, 60.9, 97.1, 118.0, 124.7, 124.9, 125.5, 127.2, 127.6, 129.3, 130.2, 131.1...

Embodiment 2

[0035] 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. 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 (ethyl acetate / methanol=20 / 1) to obtain the product 3a (20 mg, 11%) as a white solid.

Embodiment 3

[0037] 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. 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 (ethyl acetate / methanol=20 / 1) to obtain the product 3a (28 mg, 15%) as a white solid.

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Abstract

The invention discloses a synthesis and an application of a naphthalenone-sulfoxide ylide hybrid and belongs to the technical field of organic chemistry. Firstly, the naphthalenone-sulfoxide ylide hybrid is synthesized through the cascade reaction between aryl formyl sulfoxide ylide and Alpha-diazo carbonyl compound. The hybrid is capable of efficiently generating 4-hydroxy-1- naphthalene carbonylderivative under the action of raney nickel, generating 3-hydroxy-4-oxo-1- naphthalene carbonyl derivative under the action of p-toluenesulfonic acid, efficiently synthesizing 4-hydroxy-3-sulfinyl-1-naphthalene carbonyl derivative under the action of lithium chloride and methanesulfonic acid and synthesizing 3,4-dioxo-1-naphthalene carbonyl derivative under the action of lithium chloride and sulfuric acid. Thus, the naphthalenone-sulfoxide ylide hybrid has deriving diversity and has an excellent application prospect.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry, and specifically relates to the synthesis and application of a naphthone-sulfoxide ylide hybrid. Background technique [0002] Functionalized naphthalene derivatives such as: 4-hydroxy-1-naphthoate, 3-hydroxy-4-oxo-1-naphthoate, 4-hydroxy-3-sulfinyl-1-naphthoate Esters, 3,4-dioxo-1-naphthoate and 4-hydroxy-1-naphthone derivatives, etc., are commonly found in a variety of natural products, pharmaceuticals and optical / electronic materials with significant biological activities. At the same time, the ester group, carbonyl group and hydroxyl group contained in these compounds can undergo a variety of important functional group transformation reactions, and are widely used in the synthesis of drugs and functional materials. [0003] However, the synthesis methods for the above-mentioned types of compounds are still very limited, and these literature methods still have some shortcomings such...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C381/00C07C315/04C07C315/00C07C317/44C07C67/317C07C69/94C07C67/313C07C69/757
Inventor 张新迎陈茜王慕华范学森
Owner HENAN NORMAL UNIV
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