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Method for preparing N-sulfonyl-1,4-oxazine derivative

A technology of sulfonyl group and derivatives, which is applied in the field of organic synthesis and achieves the effects of simple preparation method, reduced cost, and cheap and easily available raw materials

Inactive Publication Date: 2014-11-05
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Synthesis of six-ring heterocyclic 1,4-oxazine derivatives from rhodium-catalyzed 1-sulfonyl-1,2,3-triazole compounds has not been reported

Method used

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  • Method for preparing N-sulfonyl-1,4-oxazine derivative
  • Method for preparing N-sulfonyl-1,4-oxazine derivative
  • Method for preparing N-sulfonyl-1,4-oxazine derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] In a dry 15mL pressure-resistant reaction tube, add 60mg of N-p-toluenesulfonyl-4-phenyl-1,2,3-triazole (CAS: 884866-01-7), 36mg of styrene oxide, 1.2 mg of dirhodium tetrapivalate and 0.6 ml of 1,2-dichloroethane. The reaction was stirred at 120°C for 1 hour under nitrogen. After the reaction was completed, it was cooled to room temperature, and directly passed through a silica gel column (the volume ratio of petroleum ether to ethyl acetate was 10:1) to obtain 32 mg of product with a yield of 40%. The reaction process is shown in the following formula:

[0029]

[0030] Carry out nuclear magnetic resonance and mass spectrometry to the product prepared in this embodiment:

[0031] 1 H NMR (400MHz, d 6 -acetone): δ=7.81(d,J=8.0Hz,2H),7.53(d,J=8.0Hz,2H),7.44-7.46(m,4H),7.31-7.35(m,4H),7.25- 7.29(m,2H),6.97(d,J=1.2Hz,1H),5.32(s,1H),4.53(dd,J=4.4,2.0Hz,1H),3.28(dd,J=4.4,2.0Hz ,1H),2.43(s,3H);.

[0032]13 C NMR (400MHz, d 6 -acetone): δ=144.3, 140.7, 138.4, 134.5,...

Embodiment 2

[0035] In a dry 15mL pressure-resistant reaction tube, add 63mg of 1-p-toluenesulfonyl-4-(4-methylphenyl)-1,2,3-triazole (CAS: 937801-34-8), 36 mg of styrene oxide, 1.2 mg of dirhodium tetrapivalate and 0.6 ml of 1,2-dichloroethane. The reaction solution was stirred at 120° C. for 1 hour under nitrogen. After the reaction was completed, it was cooled to room temperature, and directly passed through a silica gel column (the volume ratio of petroleum ether to ethyl acetate was 10:1), and 33 mg of the product was obtained, with a yield of 41%. The reaction process is shown in the following formula:

[0036]

[0037] Carry out nuclear magnetic resonance analysis and mass spectrometry to the product prepared in this embodiment:

[0038] 1 H NMR (400MHz, CDCl 3 ): δ=7.67(d, J=4.0Hz, 2H), 7.35-7.38(m, 4H), 7.23-7.29(m, 5H), 7.12(d, J=4.0Hz, 2H), 6.85(d, J=0.4Hz, 1H), 5.00(s, 1H), 4.38(dd, J=5.6, 0.8Hz, 1H), 3.29(dd, J=5.4, 1.4Hz, 1H), 2.41(s, 3H), 2.33(s,3H);

[0039] 13 C ...

Embodiment 3

[0042] In a dry 15mL pressure-resistant reaction tube, add 69mg of 1-p-toluenesulfonyl-4-(1-naphthyl)-1,2,3-triazole (CAS: 1562417-95-1), 36mg of Styrene and 1.2 mg of dirhodium tetrapivalate and 0.6 ml of 1,2-dichloroethane. The reaction solution was stirred at 120° C. for 1 hour under nitrogen. After the reaction was finished, it was cooled to room temperature, and directly passed through a silica gel column (the volume ratio of petroleum ether and ethyl acetate was 10:1), and 30 mg of the product was obtained, with a yield of 37%. The reaction process is shown in the following formula:

[0043]

[0044] Carry out nuclear magnetic resonance and mass spectrometry to the product prepared in this embodiment:

[0045] 1 H NMR (400MHz, CDCl 3 ):δ=7.66(d,J=4.0Hz,2H),7.35(d,J=4.0Hz,2H),7.20-7.28(m,5H),7.08(d,J=4.0Hz,1H),7.00 -7.01(m,1H),6.92(s,1H),6.81(dd,J=4.0,1.2Hz,1H),5.02(s,1H),4.39(dd,J=5.4,0.6Hz,1H), 3.79(s,3H),3.31(dd,J=5.6,0.6Hz,1H),2.41(s,3H);

[0046] 13 C NMR (...

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Abstract

The invention discloses a method for preparing a N-sulfonyl-1,4-oxazine derivative, in an organic solvent, tetracarboxylic rhodium is taken as a catalyst, a 1-sulfonyl-1,2,3-triazole compound and an epoxy compound are taken as substrates, so that the N-sulfonyl-1,4-oxazine derivative can be obtained. According to the invention, the N-sulfonyl-1,2,3-triazole compound and the epoxy compound are taken as the substrates for nitrogen removal and annulations reactions, so that N-sulfonyl-1,4-oxazine derivative can be obtained. The reaction raw materials have the advantages of simple preparation method, easy preservation, little rhodium catalyst usage, and greatly cost reduction. The method can be used for synthesizing a series of the N-sulfonyl-1,4-oxazine derivative, and the synthesized products have biological activity.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for preparing N-sulfonyl-1,4-oxazine derivatives from 1-sulfonyl-1,2,3-triazole catalyzed by tetracarboxylic acid dirhodium. Background technique [0002] Oxazine compounds, especially 1,4-oxazine derivatives, are an important class of organic heterocyclic compounds, which have important applications in photosensitive materials, enzyme inhibitors and drugs, such as the Kourounakis group (Design of Novel Potent Antihyperlipidemic Agents with Antioxidant / Anti-inflammatory Properties: Exploiting Phenothiazine's Strong Antioxidant Activity.J Med Chem.2014,57,2568-2581.) reported the research of 1,4-oxazine derivatives in antioxidant and anti-inflammatory; and (Lipid-Lowering Aromatic Tetrahydro-1,4-Oxazine Derivatives with Antioxidant and Squalene Synthase Inhibitory Activity.J Med Chem.2008,51,5861-5865) as an application of an enzyme inhibitor. At present, in order to ada...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D265/30C07D413/04
CPCC07D265/30C07D413/04
Inventor 陈万芝马学骥
Owner ZHEJIANG UNIV
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