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Synthetic method for preparing indole spiral cyclopentane derivant

A technology for the synthesis of indolespirocyclopentane, which is applied in the direction of organic chemistry, etc., can solve the problems of simple synthesis methods that are rarely reported, and achieve the effects of low cost, convenient operation, and good application prospects

Inactive Publication Date: 2013-01-16
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

With the development of indole synthetic chemistry, one-step synthesis methods of heterocyclic indole spiro derivatives such as aza and oxa have been discovered one after another, but the simple synthesis methods of indole spirocyclopentane derivatives are rarely reported.

Method used

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  • Synthetic method for preparing indole spiral cyclopentane derivant
  • Synthetic method for preparing indole spiral cyclopentane derivant
  • Synthetic method for preparing indole spiral cyclopentane derivant

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] The synthesis of embodiment 1 compound 3a

[0016]

[0017] (E)-1-benzyl-3-(3-phenyl-2-propynyl)indolin-2-one (0.1mmol), 4-phenyl-3-butyn-2-one ( 0.2mmol) was dissolved in 1mL dichloromethane / ethyl acetate (9 / 1), and the catalyst PPh was added 3 (0.05mmol), reacted at room temperature for 48h, concentrated and separated by column chromatography to obtain the corresponding indole spirocyclopentane derivative 3a with a yield of 63%. IR(KBr): v=3059, 3028, 1718, 1690, 1619, 1588, 1447, 1362, 1184, 1168, 908, 870, 762, 696cm -1 . 1 H NMR (500MHz, CDCl 3 )δ7.82 (s, 1H), 7.35-7.27 (m, 3H), 7.24-7.21 (m, 3H), 7.16-7.05 (m, 7H), 6.97 (t, J=8.0Hz, 2H), 6.89 -6.86(m, 2H), 6.82(d, J=7.5Hz, 2H), 6.78(d, J=8.0Hz, 1H), 5.08(d, J=16.0Hz, 1H), 4.36(d, J= 16.0Hz, 1H), 3.85(dd, J=11.5, 7.5Hz, 1H), 3.16(dd, J=13.0, 8.0Hz, 1H), 2.98(dd, J=13.0, 6.5Hz, 1H). 13 C NMR (125MHz, CDCl 3 )δ202.44,175.67,142.82,138.63,136.17,135.24,134.25,131.74,130.99,129.74,129.37,129.04,128.80,128.30,...

Embodiment 2

[0018] The synthesis of embodiment 2 compound 3b

[0019]

[0020] (E)-1-benzyl-5-chloro-3-(3-phenyl-2-propynyl)indolin-2-one (0.1mmol), 4-phenyl-3-butyne- 2-Kone (0.2mmol) was dissolved in 1mL dichloromethane / ethyl acetate (9 / 1), catalyst PPh3 (0.05mmol) was added, reacted at room temperature for 48h, concentrated and separated by column chromatography to obtain the corresponding indolespirocyclopentadiene Alkane derivative 3b, yield 72%. 1 H NMR (300MHz, CDCl 3 )δ7.84 (s, 1H), 7.24 (d, J=2.1Hz, 2H), 7.23-7.19 (m, 2H), 7, 19-7.17 (m, 2H), 7.17-7.01 (m, 6H) , 7.00-6.94(m, 2H), 6.80(d, J=7.2Hz, 2H), 6.68(d, J=8.3Hz, 1H), 5.04(d, J=15.8Hz, 1H), 4.37(d, J=15.8Hz, 1H), 3.83(dd, J=10.8, 8.0Hz, 1H), 3.21(dd, J=18.0, 8.0Hz, 1H), 2.96(dd, J=18.0, 10.8Hz, 1H). 13 C NMR (75MHz, CDCl 3 )δ201.97,174.42,166.50,154.59,148.63,141.49,141.37,139.20,135.41,135.22,134.79,134.05,133.99,133.08,132.16,131.74,130.04,129.89,129.25,129.16,129.02,128.93,128.90,128.70 ,128.60,128.52,128.40,128....

Embodiment 3

[0021] The synthesis of embodiment 3 compound 3c

[0022]

[0023] (E)-1-benzyl-5-chloro-3-(3-phenyl-2-propynyl)indolin-2-one (0.1mmol), 4-phenyl-3-butyne- 2-Kone (0.2mmol) was dissolved in 1mL dichloromethane / ethyl acetate (9 / 1), catalyst PPh3 (0.05mmol) was added, reacted at room temperature for 48h, concentrated and separated by column chromatography to obtain the corresponding indolespirocyclopentadiene Alkane derivative 3c, yield 58%. IR(KBr): v=3057, 3030, 2920, 2852, 1731, 1718, 1617, 1558, 1541, 1508, 1490, 1455, 1450, 1186, 1175, 861, 758, 694cm -1 . 1 H NMR (300MHz, CDCl 3)δ7.84 (s, 1H), 7.28-7.17 (m, 6H), 7.14-7.02 (m, 5H), 6.99-6.92 (m, 4H), 6.81 (d, J=7.2Hz, 2H), 6.68 (dd, J=9.3, 4.2Hz, 1H), 5.06(d, J=15.9Hz, 1H), 4.37(d, J=15.9Hz, 1H), 3.85(dd, J=11.1, 8.1Hz, 1H) , 3.21(dd, J=18.0, 8.1Hz, 1H), 2.95(dd, J=18.0, 11.1Hz, 1H). 13 C NMR (75MHz, CDCl 3 )δ201.98,175.56,160.92,139.18,138.88,135.52,134.98,134.03,131.72,129.86,129.37,129.23,128.92,128.69,128.49,1...

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Abstract

The invention belongs to the technical field of organic chemistry, and particularly relates to a synthetic method for preparing an indole spiral cyclopentane derivant. The synthetic method comprises the following steps: adopting a 3-butyn-2-one derivant and three indolone derivants substituted by methyl acetylide as raw materials, and synthetizing the indole spiral cyclopentane derivant with rich functional groups through [3+2] cycloaddition reaction under the triphenylphosphine catalysis. The indole spiral cyclopentane derivant has a broad-spectrum biological activity, and a potential application prospect in drug research and development.

Description

technical field [0001] The invention relates to the technical field of organic chemistry, in particular to a method for synthesizing indole spirocyclopentane derivatives. Background technique [0002] Indole spiro compounds are an important class of heterocyclic compounds, which widely exist in natural products and active pharmaceutical ingredients, and have various pharmacological activities. For example, it has inhibitory activity to NNRTIs type HIV-1 (Jiang T.Bioorg.Med.Chem.Lett.2006,16,2105), has antagonism to glycine receptor (Hershenson, F.M.; Prodan, K.A., et al. J. Med. Chem. 1977, 20, 1448), and tumor inhibitory activity (Numata, A., Takada, T, et al. J. Tetrahedron lett. 1993, 34, 2355). Therefore, the synthesis of indole spiro compounds has received widespread attention. With the development of indole synthesis chemistry, one-step synthesis methods of heterocyclic indole spiro derivatives such as aza and oxa have been discovered one after another, but the simpl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/96
Inventor 周庆发储雪平葛飞飞陆涛
Owner CHINA PHARM UNIV