Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Spiropyridino[2,1-a]isoquinoline compound and synthesizing method thereof

A technology of spirocyclic pyridine and synthesis method, which is applied in biocides, organic chemistry, drug combination, etc., can solve the problems of small expansion range of substrates, harsh reaction conditions, and difficult acquisition of raw materials, etc., to achieve large expansion range of substrates, The effect of high diastereoselectivity and easy availability of raw materials

Inactive Publication Date: 2018-05-18
YANGZHOU UNIV
View PDF1 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Currently spiropyrido[2,1- a ] The synthesis of isoquinoline compounds has not been reported in the literature, and the existing reports only involve the synthesis of partly combined ring structures, and there are some deficiencies, such as the expansion range of substrates is small, the raw materials are not easy to obtain, the reaction conditions are harsh, and the yield is too high. inferior

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Spiropyridino[2,1-a]isoquinoline compound and synthesizing method thereof
  • Spiropyridino[2,1-a]isoquinoline compound and synthesizing method thereof
  • Spiropyridino[2,1-a]isoquinoline compound and synthesizing method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1, preparation of 1,3-dioxo-2'-phenyl-1,3-dihydro-2' with the following structural formula H , 11b' H -Spiro[indene-2,1'-pyrido[2,1- a ]isoquinoline]-3',4'-dicarboxylic acid dimethyl ester, its reaction formula is as follows:

[0027]

[0028] Preparation:

[0029]Dissolve 0.1460 g (1.0 mmol) of 1,3-indandione in 15 mL of absolute ethanol, and add 0.0530 g (0.5 mmol) of benzaldehyde and 1.0119 g (10 mmol) of triethylamine dropwise under stirring, at 20°C The reaction was carried out for 10 hours, and suction filtration was completed after the reaction to obtain 1,3-indandione benzaldehyde.

[0030] Add 0.2340 g (1.0 mmol) 1,3-indanedionate benzaldehyde, 0.1420 g (1.0 mmol) dimethyl butynedioate and 10 mL dry acetonitrile into a round bottom flask, and add 0.1290 g ( 1.0mmol) isoquinoline, be warming up to 30 ℃, stir 0.5 hour, analyze by thin-layer chromatography, after reaction finishes, stop reaction, solvent is concentrated and evaporated on rotary evap...

Embodiment 2

[0036] Example 2, preparation of 1,3-dioxo-2'-(p-tolyl)-1,3-dihydro-2' with the following structural formula H ,11b' H -Spiro[indene-2,1'-pyrido[2,1- a ]isoquinoline]-3',4'-dicarboxylic acid dimethyl ester:

[0037]

[0038] specific method:

[0039] Dissolve 0.1460 g (1.0 mmol) of 1,3-indandione in 15 mL of absolute ethanol, and add dropwise 0.0600 g (0.5 mmol) of p-tolualdehyde and 1.5178 g (15 mmol) of triethylamine under stirring, at 25 The reaction was carried out under the condition of ℃ for 10 hours, and after the reaction was completed, it was filtered with suction to obtain 1,3-indandione acetal p-tolualdehyde.

[0040] Add 0.2340 g (1.0 mmol) 1,3-indanedione p-methylbenzaldehyde, 0.0710 g (0.5 mmol) dimethyl butyndioate and 10 mL of dry acetonitrile into a round bottom flask, and add them under stirring at room temperature 0.0645 g (0.5mmol) isoquinoline, be warming up to 45 ℃, stir 1 hour, analyze by thin-layer chromatography, after reaction finishes, stop re...

Embodiment 3

[0046] Example 3, preparation of 2'-(2-methoxyphenyl)-1,3-dioxo-1,3-dihydro-2' with the following structural formula H ,11b' H -Spiro[indene-2,1'-pyrido[2,1- a ]isoquinoline]-3',4'-dicarboxylic acid dimethyl ester:

[0047]

[0048] specific method:

[0049] 0.1460 g (1.0 mmol) of 1,3-indandione was dissolved in 15 mL of absolute ethanol, and 0.1360 g (1.0 mmol) of o-methoxybenzaldehyde and 1.5178 g (15 mmol) of triethylamine were added dropwise under stirring. The reaction was carried out at 30° C. for 11 hours. After the reaction was completed, it was filtered with suction to obtain 1,3-indandione acetal-o-methoxybenzaldehyde.

[0050]Add 0.2340 g (1.0 mmol) of 1,3-indanedione acetal-o-methoxybenzaldehyde, 0.0710 g (0.5 mmol) of dimethyl butyndioate and 10 mL of dry acetonitrile into a round bottom flask, and stir at room temperature Add 0.1290 g (1.0 mmol) isoquinoline, be warming up to 45 ℃, stir 2 hours, analyze by thin-layer chromatography, after reaction finishes...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a spiropyridino[2,1-a]isoquinoline compound and a synthesizing method thereof, and belongs to the technical field of organic synthesis. In acetonitrile, a 1,3-indandione condensed aromatic aldehyde compound, dimethyl acetylenedicarboxylate and isoquinoline are mixed to have a [4+2] cycloaddition reaction for 0.5-5 h at 30-70 DEG C, and silica gel column chromatography is conducted with a mixed solvent of ethyl acetate and petroleum ether after the addition reaction ends to obtain the spiropyridino[2,1-a]isoquinoline compound. The compound is light yellow solid, has themelting point of about 210-240 DEG C, can be easily dissolved in an organic solvent, and can be applied in medicines and pesticides.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis. Background technique [0002] Recent studies have shown that isoquinoline derivatives have certain activity as angiotensin-converting enzyme inhibitors. (Markmee, S.; Ruchirawat, S.; Prachyawarakorn, V.; Lngkaninan, K.; Khorana, N. Isoquinoline derivatives as potential acetylcholinesterase inhibitors. Bioorg. Med. Chem. Lett. 2006, 16, 2170-2172). In 2006, Trotter et al. designed and synthesized a series of 3-cyano substituted isoquinoline derivatives for the treatment of atrial fibrillation. (Trotter, B. W.; Nanda, K.K.; Kett, N. R.; Regan, C. P.; Lynch, J. J.; Stump, G. L.; Kiss, L.; Wang, J.; Spencer, R. H.; Kane, S. A.; White, R. B.; Zhang, R. .; Anderson, K. D.; Liverton, N. J.; McIntyre, C. J.; Beshore, D. C.; Hartman, G. D.; Dinsmore, C.J. Design and Synthesis of Novel Isoquinoline-3-nitrites as Orally Bioavailable Kv1.5 Antagonists for the Treatment of Atrial Fibrillation. ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07D471/10A01P3/00A01P1/00A61P31/04A61P33/02A61P21/02
Inventor 韩莹张媛媛颜朝国孙晶
Owner YANGZHOU UNIV
Features
  • Generate Ideas
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com