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A kind of synthetic method of 9h-pyrido[2,3-b]indole compound

A synthetic method, 3-b technology, applied in the direction of organic chemistry, etc., can solve the problems of application limitation, expensive substrate, low product yield, etc., and achieve the effect of simple operation, wide application range, and cheap and easy-to-obtain raw materials

Inactive Publication Date: 2016-08-31
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Since most of these literature methods require multi-step synthesis and separation and purification processes, and the product yield is low and the substrate is expensive, its application in actual production is limited.

Method used

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  • A kind of synthetic method of 9h-pyrido[2,3-b]indole compound
  • A kind of synthetic method of 9h-pyrido[2,3-b]indole compound
  • A kind of synthetic method of 9h-pyrido[2,3-b]indole compound

Examples

Experimental program
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Effect test

Embodiment 1

[0011]

[0012] In a 25 mL reaction tube, add 1a (0.5 mmol, 170 mg), 2a (0.75 mmol, 95 mg), cuprous iodide (0.05 mmol, 9.5 mg), triethylenediamine (0.1 mmol, 11.2 mg), Trimethylacetic acid (0.5 mmol, 51 mg) and N,N-dimethylformamide (3 mL), then concentrated aqueous ammonia (7 mmol, 0.5 mL) was added. Heated to 80°C under air, stirred for 30 hours, added 5 mL of saturated ammonium chloride solution to quench the reaction, extracted with ethyl acetate (10 mL × 2), and then washed the organic phase with water and saturated brine in sequence, and anhydrous Na2SO4 dried. Filtrated, spin-dried, and separated by silica gel column (petroleum ether / ethyl acetate=10 / 1) to obtain the white solid product 3-ethyl-2-propyl-9H-pyridine[2,3-b]indole 3a (61 mg, 51%). The characterization data of this compound are as follows: 1 H NMR (400 MHz, CDCl 3 ) δ: 1.06 (t, J = 7.2 Hz,3H), 1.35 (t, J = 7.2 Hz, 3H), 1.80-1.90 (m, 2H), 2.85 (q, J = 8.0 Hz, 2H), 2.98 ( t, J = 8.0 Hz, 2H), 7.25 (t, ...

Embodiment 2

[0014] According to the method described in Example 1, 1a (0.5 mmol, 170 mg), 2a (0.75 mmol, 95 mg), cuprous iodide (0.05 mmol, 9.5 mg), triethylenedi Amine (0.1 mmol, 11.2 mg), trimethylacetic acid (0.5 mmol, 51 mg) and N,N-dimethylformamide (3 mL), then concentrated aqueous ammonia (7 mmol, 0.5 mL) was added. After heating to 100°C under air and stirring for 30 hours, the product 3-ethyl-2-propyl-9H-pyridino[2,3-b]indole 3a (48 mg, 40%) was obtained.

Embodiment 3

[0016] According to the method described in Example 1, 1a (0.5 mmol, 170 mg), 2a (0.75 mmol, 95 mg), cuprous iodide (0.05 mmol, 9.5 mg), triethylenedi Amine (0.1 mmol, 11.2 mg), trimethylacetic acid (0.5 mmol, 51 mg) and dimethyl sulfoxide (3 mL), then concentrated aqueous ammonia (7 mmol, 0.5 mL) was added. After heating to 80°C under air and stirring for 30 hours, the product 3-ethyl-2-propyl-9H-pyridino[2,3-b]indole 3a (51 mg, 43%) was obtained.

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Abstract

The invention discloses a synthesis method of 9H-pyridino[2,3-b]indole compounds, belonging to the technical field of organic synthesis. The technical scheme is as follows: the synthesis method comprises the following steps: dissolving 1-bromo-2-(2,2-dibromovinyl)benzene or derivatives thereof, ammonia water and alpha,beta-unsaturated aldehyde compounds in an organic solvent, adding a catalyst transition metal salt and an additive, and reacting at 60-100 DEG C in the presence of air to obtain the 9H-pyridino[2,3-b]indole compounds. The synthesis process is one-pot multicomponent series reaction, is simple to operate, avoids waste of resources and environmental pollution caused by the use of multiple reagents in multiple reaction steps, the purification treatment on the intermediate in each reaction step and the like, and provides an economical, practical, green and environment-friendly novel method for synthesizing the 9H-pyridino[2,3-b]indole compounds.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of 9H-pyrido[2,3-b]indole compounds. Background technique [0002] Indole and its derivatives widely exist in nature, and have a broad spectrum of physiological and biological activities, and have been widely concerned by chemists for many years. Among them, 9H-pyrido[2,3-b]indole, also known as α-carboline, is a very important indole derivative and an important structural unit of natural products such as dendrodoine A, grossularines, and cryptotackiene. In addition, many carboline derivatives from natural sources and artificially synthesized have significant antiviral and anticancer activities, which have important research value. At present, the synthesis methods of such compounds mainly include the cyclization of 2-aminoindole and the ring-forming splicing of indole and pyridine. Most of these literature methods require multi-step syn...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 范学森李彬张新迎郭胜海张举沈娜娜
Owner HENAN NORMAL UNIV
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