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Novel diazo benzothiapyrone photosensitive protecting groups and synthesis method thereof

A technology of benzothiopyrone and diazobenzene, which is applied in the field of preparation of new compounds, can solve the problems of increased difficulty in experimental operation, inconvenient experiment, and reduced reaction yield, and achieves efficient and rapid photodissociation reactions with good relative The effect of stability

Inactive Publication Date: 2015-04-01
TIANJIN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method has disadvantages in implementing
The protecting group has its unique properties, and specific reagents must be used when performing up-protection and deprotection. In multi-step synthesis, this virtually increased two-step reaction will bring great inconvenience to the experiment, and will make The yield of the reaction is greatly reduced, especially when there are multiple sites in a molecule that need to be protected, the difficulty of experimental operation will increase

Method used

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  • Novel diazo benzothiapyrone photosensitive protecting groups and synthesis method thereof
  • Novel diazo benzothiapyrone photosensitive protecting groups and synthesis method thereof
  • Novel diazo benzothiapyrone photosensitive protecting groups and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] A preparation of 1,1-dioxo-2-diazo-3-phenyl-4H-benzothiopyrone, the specific steps are as follows:

[0060] ⑴2-Methyl-4H-benzothiopyrone

[0061] 12.5g H 3 PO 4 , 18gP 2 o 5 Stir at 70°C, after dissolving, add the mixture of 1.5mL thiophenol and 1.5mL ethyl acetoacetate dropwise (15min) with a constant pressure dropping funnel, react for 3 hours, pour into ice water, extract with ethyl acetate, The organic layer was washed with 10% NaOH aqueous solution (20mL×3), adjusted to pH=9, after washing with water, the organic layer was washed with anhydrous MgSO 4 After drying, the obtained product was concentrated and crystallized with ether to obtain 1.6 g of yellow crystals, with a yield of 77.4%.

[0062] 1 H-NMR (CDCl 3 / TMS) δ: 8.48(1H, J=7.9Hz, d), 7.56-7.52(2H, m), 7.50(1H, J=7.6, 7.9Hz, dd), 6.82(1H, s), 2.44(3H ,s).

[0063] 13 C-NMR (CDCl 3 )δ: 180.63, 151.32, 137.64, 131.35, 130.70, 128.54, 127.48, 125.98, 124.89, 23.31.

[0064] ⑵3-iodo-2-methyl-4H-benz...

Embodiment 2

[0089] 1,1-dioxo-2-diazo-3-p-methoxyphenyl-4H-benzothiopyrone was synthesized by the same method as in Example 1, and the yield was 84%.

[0090] 1 H-NMR (CDCl3) δ: 8.21 (1H, d, J = 7.9Hz), 8.09 (1H, d, J = 7.9Hz), 7.89 (1H, dd, J = 7.9, 7.9Hz), 7.78 (1H, dd,J=7.9,7.9Hz),7.35(2H,d,J=9.2Hz),7.00(2H,d,J=9.2Hz),5.03(1H,s),3.86(3H,s).

[0091] 13 C-NMR (CDCl 3 )δ: 178.94, 160.63, 147.08, 142.50, 139.96, 134.54, 133.33, 131.18, 129.22, 129.03, 122.99, 122.66, 113.80, 55.32, 47.01.

Embodiment 3

[0093] The synthesis of 1,1-dioxo-2-diazo-3-(3,5-bis(trifluoromethyl))phenyl-4H-benzothiopyrone, the method is the same as in Example 1, and the yield 75%.

[0094] 1 H-NMR (CDCl 3 )δ: 8.25 (1H, d, J = 7.9Hz), 8.13 (1H, d, J = 7.9Hz), 8.02 (1H, s), 7.96 (1H, dd, J = 7.9, 7.9Hz), 7.92 ( 2H,s),7.85(1H,dd,J=7.9,7.9Hz),5.05(1H,s).

[0095] 13 C-NMR (CDCl 3 )δ: 177.79, 149.68, 139.85, 139.81, 135.22, 133.74, 132.58, 132.00, 131.73, 131.46, 130.20, 129.23, 128.56, 124.04, 123.39, 121.87, 46.54.

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Abstract

The invention discloses novel diazo benzothiapyrone photosensitive protecting groups and a synthesis method thereof. A compound disclosed by the invention can be used for protecting a phosphoric acid functional group compound. The novel benzothiapyrone photosensitive protecting groups disclosed by the invention are efficient and rapid in photo-dissociation reaction, have good relative stability under daily illumination conditions, and also have unique photosensitive structures which have response to light and can also be used for releasing potential fluorescent groups. According to the novel diazo benzothiapyrone photosensitive protecting groups disclosed by the invention, tracking and monitoring of a light control process can be facilitated, and the 'controllability' and 'visibility' of release can be achieved; and a novel research method for performing quantitative release and accumulation degree research under cell biological environments can be provided.

Description

technical field [0001] The invention belongs to a preparation method of a new compound, in particular to a novel diazothiopyrone photosensitive protecting group and a synthesis method. Background technique [0002] In order to selectively carry out a certain reaction during an organic reaction, it is necessary to use a specific group to protect the sensitive functional group or interfering functional group in the molecule, and this type of group is a protecting group. However, this approach has disadvantages in its implementation. The protecting group has its unique properties, and specific reagents must be used when performing up-protection and deprotection. In multi-step synthesis, this virtually increased two-step reaction will bring great inconvenience to the experiment, and will make The yield of the reaction is greatly reduced, especially when there are multiple sites in a molecule that need to be protected, the difficulty of experimental operation will increase. [...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D335/06C07F9/6553
CPCC07D335/06C07F9/655372Y02P20/55
Inventor 张有来张欢刘珊珊马驰程艳丽洪丽虹李保芬杜旭泽
Owner TIANJIN UNIVERSITY OF TECHNOLOGY
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