Indolo-pyrroloquinoline compounds and synthesis method thereof

A technology of indolopyrrole and synthesis method, applied in directions such as organic chemistry, can solve the problems of small expansion range of substrates, harsh reaction conditions, difficult to obtain raw materials, etc., and achieves large expansion range of substrates and high diastereoselectivity. , the effect of high yield

Inactive Publication Date: 2018-05-11
YANGZHOU UNIV
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Problems solved by technology

[0004] At present, the synthesis research of indolopyrroloquinoline compounds has not been reported in the literature, and the existing reports only involve the synthesis of part of the ring structure, and there are some shortcomings, such as the expansion range of substrates is small, the raw materials are not easy to obtain, and the reaction conditions are relatively harsh. , the yield is too low, etc., so the synthesis of indolopyrroloquinoline compounds has a good application prospect

Method used

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  • Indolo-pyrroloquinoline compounds and synthesis method thereof
  • Indolo-pyrroloquinoline compounds and synthesis method thereof
  • Indolo-pyrroloquinoline compounds and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Example 1, preparation of 3',3'-dicyano-2-oxo-3',3a'-dihydro-1'H-spiro[indoline-3,2'-pyrrolo with the following structural formula [1,2-a]quinoline]-1'-ethyl carboxylate, the reaction formula is as follows:

[0025]

[0026] The preparation method is as follows:

[0027] In a 50mL round bottom flask, add 0.2950g (1.0mmol) quinoline quaternary ammonium salt, 0.1950g (1.0mmol) isatin malononitrile, 0.1517g (1.5mmol) Et 3 N was used as a basic catalyst and 10 mL of dry acetonitrile was used as a solvent, stirred at room temperature for 12 hours, and the reaction progress was detected by thin-layer chromatography.

[0028] After the reaction was completed, the solvent was concentrated and evaporated on a rotary evaporator, and separated by column chromatography (mixing ethyl acetate and petroleum ether in a volume ratio of 1:3, and used as a developing solvent for column chromatography separation) to obtain pure 3' , 3'-dicyano-2-oxo-3',3a'-dihydro-1'H-spiro[indoline-3...

Embodiment 2

[0031] Example 2, preparation of 5-chloro-3', 3'-dicyano-2-oxo-3', 3a'-dihydro-1'H-spiro[indoline-3,2 Ethyl '-pyrrolo[1,2-a]quinoline-1'-carboxylate:

[0032]

[0033] In a 50mL round bottom flask, add 0.2950g (1.0mmol) quinoline quaternary ammonium salt, 0.1950g (1.0mmol) isatin malononitrile, 0.1517g (1.5mmol) Et 3 N was used as a basic catalyst and 10 mL of dry acetonitrile was used as a solvent, stirred at room temperature for 12 hours, and the reaction progress was detected by thin-layer chromatography.

[0034] After the reaction was completed, the solvent was concentrated and evaporated on a rotary evaporator, and separated by column chromatography (mixing ethyl acetate and sherwood oil with a volume ratio of 1:3, and performing column chromatography separation as a developer), in Example 1 , the isatin malononitrile used is replaced with 5-chloroisatin malononitrile in equimolar amounts, and other steps are the same as in Example 1 to obtain 5-chloro-3', 3'-dicyano...

Embodiment 3

[0037] Example 3, preparation of 3',3'-dicyano-5-methyl-2-oxo-3',3a'-dihydro-1'H-spiro[indoline-3, 2'-Pyrrolo[1,2-a]quinoline]-1'-carboxylic acid ethyl ester:

[0038]

[0039] In Example 1, the isatin malononitrile used is replaced with an equimolar amount of 5-methyl isatin malononitrile, and the other steps are the same as in Example 1 to obtain 3', 3'-dicyano-5-methanol yl-2-oxo-3',3a'-dihydro-1'H-spiro[indoline-3,2'-pyrrolo[1,2-a]quinoline]-1'-carboxylic acid Ethyl ester, its isolated yield is 87%, and structural characterization data is as follows:

[0040] 1 H NMR (400 MHz, DMSO- d 6 ) δ: major isomer: 11.34 (s, 1H, NH), 7.44 (m,1H, ArH), 7.35 (d, J = 8.0 Hz, 1H, ArH), 7.12-7.06 (m, 2H, ArH), 6.96-6.87(m, 2H, ArH), 6.78-6.71 (m, 1H, ArH), 6.50 (d, J = 8.0 Hz, 1H, ArH), 6.06-6.05 (m, 1H, ArH), 5.92-5.86 (m, 1H, CH), 5.16 (s, 1H, CH), 4.19-4.13 (m, 1H, CH) , 3.98-3.92 (m, 1H, CH), 2.30 (s, 3H, CH 3 ), 1.06 (t, J = 7.2 Hz, 3H, CH 3 ); minor isomer: 11.37 (s...

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Abstract

The invention discloses indolo-pyrroloquinoline compounds and a synthesis method thereof and belongs to the technical field of organic synthesis. Quinoline quaternary ammonium salt and 2-(2-oxoindol-3-ylidene)malononitrile compounds are mixed and stirred at the normal temperature to react, column chromatography on silica gel is performed with a mixed solvent of ethyl acetate and petroleum ether after the reaction, spiro[dihydroindole-3,2'-pyrrolo[1,2-a]quinoline] compounds are obtained. The method for synthesizing spiro[dihydroindole-3,2'-pyrrolo[1,2-a]quinoline] compounds has the characteristics that the reaction condition is mild, raw materials are easy to use, the substrate expansion range is wide, the operation is simple, the yield is high and the diastereoselectivity is high. The target molecular structure has not been reported in literature yet at present and has important application value in various fields such as medicine, pesticide, bioscience and the like.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis. Background technique [0002] Many quinoline compounds are important pharmaceutical intermediates and drugs. Recent studies have shown that quinoline compounds also have good antihypertensive effects (Muruganantham, N., Sivakumar, R., Anbalagan, N., et al. Synthesis , anticonvu-lsant and antihypertensive activities of 8-substituted quinoline derivatives. [J]. Biol Pharm Bull, 2004, 27(10), 1683-1687), the newly designed and synthesized quinoline derivatives with complex structure can directly act on have antitumor activity on tumor cells (Bekhit, A. A., El-Sayed, O. A., Al-Allaf, T. A., et al. Synthesis, characterization-on and cytotoxicity evaluation of some new platinum(II) complexes of tetraz-olo [l , 5-a]quinolines. [J]. Eur J Med Chem, 2004, 39(6)., 499-505), the quinoline drugs synthesized by Li et al. can inhibit the growth of new blood vessels in the tumor and thus have a relat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/20
Inventor 孙晶张瑜颜朝国韩莹
Owner YANGZHOU UNIV
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