Method for preparing indolotetrahydropyridinedione and derivative thereof through photo-initiated free radical cascade reaction and product

A technology of tetrahydropyridinedione and indole derivatives, which is applied in the field of organic compound preparation and can solve problems such as application limitations

Pending Publication Date: 2021-12-31
SOUTHWEST UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Overall, however, their applications are limited due to the need for high-energy conditions such as high temperature, UV exposure, or stoichiometrically toxic reagents or oxidants

Method used

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  • Method for preparing indolotetrahydropyridinedione and derivative thereof through photo-initiated free radical cascade reaction and product
  • Method for preparing indolotetrahydropyridinedione and derivative thereof through photo-initiated free radical cascade reaction and product
  • Method for preparing indolotetrahydropyridinedione and derivative thereof through photo-initiated free radical cascade reaction and product

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] The compound (2,4,5-trimethyl-4-(2-oxo-2-phenylethyl)-4,5-dihydro-1H-pyrido[4,3-b]indole-1,3 for preparation of structural formula I-1 (2H)-dione), the preparation method is as follows:

[0036] (1) Add 0.2mmol R 1 for -CH 3 , R 2 for -CH 3 Indole derivatives (structural formula II-1), 0.4mmol of 2,6-lutidine (2,6-lutidine) and 1.0mmol of acid chloride (R 3 -Cl, where R 3 for ) into a round-bottomed flask equipped with a magnetic stirrer, adding the face formula three (2-phenylpyridine) iridium (fac-Ir(ppy) 3 ) (3mol%, relative to the addition of indole derivatives), vacuumize and backfill with argon (three times);

[0037] (2) Inject 2 mL of degassed and dried organic solvent (CH 2 Cl 2 ), at room temperature, under an argon atmosphere (argon balloon), irradiate with a blue LED lamp with a power of 9W, stir and react for 4h to obtain a mixture (the reaction is monitored by thin-layer chromatography, and the indole derivative is reacted until the solution is n...

Embodiment 2

[0042] The compound (2,4,5-trimethyl-4-(2-oxo-2-(p-tolyl)ethyl)-4,5-dihydro-1H-pyrido[4,3-b] of preparation structure I-2 indole-1,3(2H)-dione), the preparation method is as follows:

[0043] R in Example 1 3 for The acid chloride is replaced by R 3 for acid chloride, and the rest were reacted according to the method in Example 1 to prepare 56.9 mg of a compound of structural formula I-2 (white solid, yield 76%).

[0044] 1 H NMR (600MHz, Chloroform-d) δ8.41–8.31(m,1H),7.76(d,J=8.0Hz,2H),7.34–7.28(m,3H), 7.24(d,J=8.0Hz, 2H), 4.34(d, J=18.0Hz, 1H), 4.10(d, J=18.0Hz, 1H), 3.83(s, 3H), 3.42(s, 3H), 2.41(s, 3H), 1.77( s, 3H). 13 C NMR (151MHz, Chloroform-d) δ195.0, 176.3, 162.4, 146.7, 144.7, 138.4, 133.2, 129.4, 128.1, 124.8, 123.4, 122.6, 121.5, 109.2, 104.5, 47.0, 44.0, 31.9, 26.6 .

[0045] HRMS(ESI)calcd.for C 23 h 22 N 2 o 3 [M+Na] + :397.1523, found 397.1532.

Embodiment 3

[0047] The preparation structural formula is the compound (4-(2-(4-(tert-butyl)phenyl)-2-oxoethyl)-2,4,5-trimethyl-4,5-dihydro-1H-pyrido[4, 3-b] indole-1,3(2H)-dione), the preparation method is as follows:

[0048] R in Example 1 3 for The acid chloride is replaced by R 3 for acid chloride, and the rest were reacted according to the method in Example 1 to prepare 58.3 mg of a compound of structural formula I-3 (white solid, yield 70%).

[0049] 1 H NMR (600MHz, Chloroform-d) δ8.36 (dd, J = 5.9, 2.5Hz, 1H), 7.80 (d, J = 8.2Hz, 2H), 7.45 (d, J = 8.2Hz, 2H), 7.34 –7.28(m,3H),4.35(d,J=18.0Hz,1H),4.10(d,J=18.0Hz,1H),3.84(s,3H),3.42(s,3H), 1.77(s, 3H), 1.34(s, 9H). 13 C NMR (151MHz, Chloroform-d) δ195.1, 176.3, 162.4, 157.6, 146.7, 138.4, 133.1, 125.7, 124.8, 123.4, 122.6, 121.5, 109.2, 104.4, 47.0, 44.0, 35.2, 32.0, 21.0, .

[0050] HRMS(ESI)calcd.for C 26 h 28 N 2 o 3 [M+Na] + : 439.1992, found 439.1993.

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Abstract

The invention relates to a method for preparing indolotetrahydropyridinedione and derivative thereof through photo-initiated free radical cascade reaction and a product, and belongs to the technical field of organic compound preparation. The invention discloses the method for preparing indolo tetrahydropyridinedione and a derivative thereof by photo-initiated free radical cascade reaction. The method mainly comprises the following steps: carrying out illumination reaction on an indole derivative and any one of acyl chloride or sulfonyl chloride in the presence of alkali under the catalysis of facic-Ir (ppy) 3 to obtain the indolo tetrahydropyridinedione and the derivative. The method belongs to a photo-oxidation reduction catalytic tandem cyclization reaction between a Michael receptor and a free radical (wherein the free radical is derived from acyl chloride or sulfonyl chloride). According to the preparation method of the photo-initiated free radical tandem reaction, free radical sources are wide, and a simple solution is provided for simple synthesis of various indolo tetrahydropyridinedione derivatives through a free radical tandem strategy.

Description

technical field [0001] The invention belongs to the technical field of organic compound preparation, and relates to a method and a product for preparing indolotetrahydropyridinedione and its derivatives through a series reaction of free radicals induced by light. Background technique [0002] Heterocyclic compounds are among the most important structures in chemicals, especially in pesticides, herbicides, natural products and pharmaceuticals. It is estimated that more than 50% of published chemical literature contains heterocyclic structures, and 70% of drug products have heterocyclic structures. Bicyclic aromatic heterocycles containing nitrogen atoms, such as quinoline, isoquinoline, and indole, are commonly found in Organic compounds in the fields of biology and medicine. In particular, more than 10,000 biologically active indole derivatives have been identified so far. Of these, more than 200 are currently labeled as drugs or are in clinical trials. Moreover, indole n...

Claims

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Application Information

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IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 官智杨得勇何延红
Owner SOUTHWEST UNIVERSITY
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