Aza medium ring lactone compound and preparation method thereof

A technology for cyclic lactones and compounds, applied in the field of compound preparation, can solve rare problems and the like, and achieve the effects of short reaction time, high product yield, and convenient and easy-to-obtain raw materials

Inactive Publication Date: 2021-04-09
BEIJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In contrast, at present, vinyl ethylene carbonate is used as a building block in organic synthesis for the construction of azalide compounds.

Method used

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  • Aza medium ring lactone compound and preparation method thereof
  • Aza medium ring lactone compound and preparation method thereof
  • Aza medium ring lactone compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033]

[0034] Weigh 1a (38.0mg, 0.2mmol), 2a (17.7mg, 0.1mmol), palladium catalyst (2.9mg, 0.0025mmol) and ligand PPh 3 (2.6mg, 0.01mmol) was dissolved in 1mL of ethyl acetate, heated and stirred at 60°C for 5 hours (reaction detected by TLC), after the reaction was complete, the crude product was subjected to column chromatography to obtain the target product 3aa (31.8mg) , the yield was 98%.

[0035] Characterization and analysis of target objects:

[0036] 3aa: white solid, 1 H NMR (400MHz, CDCl 3 ): δ7.58(d, J=7.2Hz, 1H), 7.51-7.47(m, 3H), 7.41-7.33(m, 3H), 7.27-7.25(m, 2H), 6.11(t, J=6.8 Hz, 1H), 5.26(s, 2H), 4.69(d, J=6.0Hz, 2H), 3.45(s, 3H)ppm; 13 C NMR (100MHz, CDCl 3 ): δ167.9, 154.2, 145.8, 141.1, 140.8, 131.3, 130.0, 128.6, 128.2, 127.5, 126.8, 125.4, 124.6, 124.5, 64.1, 61.6, 38.1ppm; HRMS (ESI) m / z: C 19 h 17 NO 4 [M+H] + The theoretical calculation value is 324.1230, and the measured value is 324.1218.

Embodiment 2

[0038]

[0039] Weigh 1a (38.0mg, 0.2mmol), 2b (21.2mg, 0.1mmol), palladium catalyst (2.9mg, 0.0025mmol) and ligand PPh 3 (2.6mg, 0.01mmol) was dissolved in 1mL of ethyl acetate, heated and stirred at 60°C for 4 hours (reaction detected by TLC), after the reaction was complete, the crude product was subjected to column chromatography to obtain the target product 3ab (31.1mg) , the yield was 87%.

[0040] Characterization and analysis of target objects:

[0041] 3ab: white solid, 1 H NMR (400MHz, CDCl 3 ): δ7.55(s,1H),7.49(d,6.4Hz,2H),7.45-7.36(m,4H),7.20(d,J=8.8Hz,1H),6.13(t,J=8.0Hz ,1H),5.26(s,2H),4.68(d,J=4.8Hz,2H),3.42(s,3H)ppm; 13 C NMR (100MHz, CDCl 3 ): δ166.6, 153.9, 145.9, 140.8, 139.4, 131.4, 131.2, 131.0, 128.6, 128.3, 127.5, 126.8, 125.9, 124.4, 64.3, 61.6, 38.1ppm; HRMS (ESI) m / z: C 19 h 16 ClNO 4 [M+H] + The theoretically calculated value is 358.0841, and the measured value is 358.0827.

Embodiment 3

[0043]

[0044] Weigh 1b (53.8mg, 0.2mmol), 2a (17.7mg, 0.1mmol), palladium catalyst (2.9mg, 0.0025mmol) and ligand PPh 3(2.6mg, 0.01mmol) was dissolved in 1mL of ethyl acetate, heated and stirred at 60°C for 2 hours (reaction detected by TLC), after the reaction was complete, the crude product was subjected to column chromatography to obtain the target product 3ba (34.9mg) , the yield was 87%.

[0045] Characterization and analysis of target objects:

[0046] 3ba: white solid, 1 H NMR (400MHz, CDCl 3 ): δ7.57(d, J=7.2Hz, 1H), 7.51-7.47(m, 3H), 7.36(d, J=8.0Hz, 2H), 7.27-7.25(m, 2H), 6.09(t, J=6.4Hz, 1H), 5.19(s, 2H), 4.67(d, J=4.8Hz, 2H), 3.43(s, 3H)ppm; 13 C NMR (100MHz, CDCl 3 ): δ167.8, 154.1, 144.5, 140.9, 140.1, 131.7, 131.3, 130.0, 128.5, 127.5, 125.5, 125.0, 124.6, 122.3, 64.1, 61.3, 38.1ppm; HRMS (ESI) m / z: C 19 h 16 BrNO 4 [M+H] + The theoretical calculation value is 402.0336, and the measured value is 402.0321.

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Abstract

The invention discloses an aza medium ring lactone compound and a preparation method thereof, and belongs to the technical field of compound preparation. According to the invention, the [5 + 6] cycloaddition reaction of vinyl ethylene carbonate and isatin anhydride is constructed for the first time,so that the chemical synthesis of aza medium ring lactone is efficiently and simply realized; specifically, vinyl ethylene carbonate and isatin anhydride are used as synthetic building blocks, a metal palladium catalyst and a phosphorus-containing ligand are added, and a target product is obtained through a reaction under a heating condition of 50-70 DEG C; the preparation method is simple to operate, quick in reaction, high in product yield, simple in aftertreatment and wide in substrate application range; and the synthesis method is a brand-new and efficient synthesis method of the aza medium ringlactone compound with potential biological activity and medicinal value.

Description

technical field [0001] The invention specifically relates to a preparation method of an azalide compound, which belongs to the technical field of compound preparation. Background technique [0002] Azalides are a class of heterocyclic compounds with unique chemical structures. As the dominant drug skeleton structure, they widely exist in active natural products and drug molecular structures, such as anti-inflammatory, anti-fungal, anti-tumor, anti-viral and anti-inflammatory drugs. parasites etc. At present, there are many reports on the synthesis of azamacrolides. In contrast, the construction of azalide compounds faces great difficulties, mainly due to the need to overcome unfavorable entropy effects and cross-ring interactions when constructing azalide compounds. At present, there are few reports on the synthesis methods of azalides, and there is still a lot of room for development. Therefore, the design and development of new, efficient, environmentally friendly, and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D273/01
CPCC07D273/01
Inventor 赵洪武吴慧慧范晓祖张恒汤喆毕晓帆蔡璐羽
Owner BEIJING UNIV OF TECH
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