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Polysubstituted thiapyran derivative and synthesis method thereof

A synthetic method and a multi-substituted technology are applied in the field of multi-substituted thiopyran derivatives and their synthesis to achieve the effects of wide applicability, good stereoselectivity and high yield of target products

Active Publication Date: 2022-04-22
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, most of these methods require noble metal catalysis, and the method using Lewis acid as catalyst has not been reported yet.

Method used

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  • Polysubstituted thiapyran derivative and synthesis method thereof
  • Polysubstituted thiapyran derivative and synthesis method thereof
  • Polysubstituted thiapyran derivative and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040]

[0041] In the glove box, weigh 1-methylthio-1-benzylamine-1-butene-3-phenyl-3-thione 2a (0.3mmol), butynedioic acid dimethyl ester 3 (0.45mmol ), zinc chloride (0.03mmol) in a 25mL Schlenk reaction flask, under nitrogen, add DMF 2mL, put into 120 ℃ oil bath and react for 12 hours. After the reaction, the mixture was cooled to room temperature, and the volatile components were removed under reduced pressure, and then separated by silica gel column chromatography (eluent was petroleum ether (60-90°C) / ethyl acetate, v / v=20:1 ), to obtain the yellow liquid target product 1a (92 mg, yield 81%). The target product was confirmed by NMR and high-resolution mass spectrometry.

[0042] Compound Characterization Data

[0043] 6-Phenyl-4-anilino-4hydro-thiopyran derivative (1a), yellow solid. 1 H NMR (400MHz, CDCl 3 )δ7.01(m,2H),6.92(m,4H),6.63-6.45(m,5H),3.69(s,3H),3.63(s,3H). 13 C{ 1 H}NMR (100MHz, CDCl 3 )δ162.0, 157.0, 151.3, 150.4, 140.1, 138.3, 135.2, 131.0, 126.9,...

Embodiment 2

[0045]

[0046] In the glove box, weigh 1-methylthio-1-p-toluidine-1-butene-3-o-bromophenyl-3-thione 2b (0.3mmol), dimethyl butyndioate 3 (0.45mmol), zinc chloride (0.03mmol) in a 25mL Schlenk reaction flask, under nitrogen, add DMF 2mL, and put it in an oil bath at 120°C for 12 hours. After the reaction, the mixture was cooled to room temperature, and the volatile components were removed under reduced pressure, and then separated by silica gel column chromatography (eluent was petroleum ether (60-90°C) / ethyl acetate, v / v=20:1 ), to obtain the yellow liquid target product 1b (108mg, yield 85%). The target product was confirmed by NMR and high-resolution mass spectrometry.

[0047] Compound Characterization Data

[0048] 6-o-methylphenyl-4-p-methoxyanilino-4hydro-thiopyran derivative (1b), yellow solid. 1 H NMR (400MHz, CDCl 3 )δ7.01(m,1H),6.90(m,3H),6.61-6.44(m,5H),3.69(s,3H),3.62(s,3H),3.46(s,3H),2.00(s ,3H). 13 C{ 1 H}NMR (100MHz, CDCl 3 C 23 h 21 NO 5 HRMS theore...

Embodiment 3

[0050]

[0051] In the glove box, successively weigh 1-ethylthio-1-ethylamine-1-butene-3-naphthyl-3-thione 2c (0.3mmol), butyndioic acid di-tert-butyl ester 4 ( 0.45mmol) (Aldrich CAS: 66086-33-7), zinc chloride (0.03mmol) in a 25mL Schlenk reaction flask, under nitrogen, add DMF 2mL, and put it in an oil bath at 120°C for 12 hours. After the reaction, the mixture was cooled to room temperature, and the volatile components were removed under reduced pressure, and then separated by silica gel column chromatography (eluent was petroleum ether (60-90°C) / ethyl acetate, v / v=20:1 ), the target product 1c (74 mg, yield 53%) was obtained as a yellow liquid. The target product was confirmed by NMR and high-resolution mass spectrometry.

[0052] Compound Characterization Data

[0053] 6-Naphthyl-4-ethylamino-4hydro-thiopyran derivative (1c), yellow liquid. 1 H NMR (400MHz, CDCl 3 )δ7.05(m,1H),6.94(m,2H),6.65-6.40(m,4H),4.11(q,J=7.1Hz,2H),1.55(s,9H),1.45(s,9H ), 1.09(t,J=7.1Hz,3H...

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Abstract

The invention discloses a polysubstituted thiapyran derivative and a synthesis method thereof. Alpha-thiocarbonyl-N, S-ketene and butynoic acid ester are used as starting materials, Lewis acid is used as an accelerant, a thiapyran ring is constructed in one step, a series of polysubstituted thiapyran derivatives are generated, and the obtained polysubstituted thiapyran derivatives have certain potential pharmaceutical activity. The method has the advantages of easily available raw materials, simple operation, mild synthesis reaction conditions, high reaction efficiency and diversity of functional groups.

Description

technical field [0001] The invention belongs to the technical field of thiopyran compounds, and in particular relates to a multi-substituted thiopyran derivative and a synthesis method thereof. Background technique [0002] Thiopyran compounds are very important six-membered heterocyclic derivatives. Many natural product molecules contain thiopyran skeletons. Antibiotics with thiopyran rings have better efficacy than phenyl homologues. Therefore, it is of great significance to develop new methods for the synthesis of thiopyran derivatives. At present, there are two main methods for the synthesis of thiopyran derivatives: functionalization on the basis of existing thiopyran rings or ring-closing reactions using simple substrates. However, most of these methods require noble metal catalysis, and methods using Lewis acids as catalysts have not been reported yet. Contents of the invention [0003] The purpose of the present invention is to use α-thiocarbonyl-N,S-ketal II, wh...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D335/02
CPCC07D335/02Y02P20/55
Inventor 余正坤何媛
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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