2,3-disubstituted indoline compound as well as preparation method and application thereof

A compound, indoline technology, applied in organic chemistry, bulk chemical production, etc., can solve disclosure problems

Pending Publication Date: 2020-06-05
INST OF NEW MATERIALS & IND TECH WENZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although many significant advances have been made, the aforementioned arylation and cy

Method used

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  • 2,3-disubstituted indoline compound as well as preparation method and application thereof
  • 2,3-disubstituted indoline compound as well as preparation method and application thereof
  • 2,3-disubstituted indoline compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] In the Schlenk capped reactor at room temperature, the imine-alkyne amine compound (0.1 mmol) protected by tert-butylsulfonyl (Bus) shown in formula I-1 and phenylboronic acid (0.2 mmol) shown in formula II were added successively. mmol), CuOTf (0.01mmol), the reactor was protected with argon, and anhydrous methanol (0.25mL) was added with a syringe, and then the reactor was placed at 50°C (oil bath) and stirred for 19h, and the reaction was completely monitored by TLC , followed by adding 0.01 mol of diethyl phthalate as an internal standard to the reaction solution, concentrating the reaction solution, taking a sample for nuclear magnetic detection, calculating the yield III-1 to be 50%, and the raw material hydrolyzate <1%.

Embodiment 2

[0057] The catalyst was replaced by CuI, and the reaction time was 48 hours until the raw materials were completely consumed. Other conditions were the same as in Example 1. The yield of III-1 NMR was 20%, and the yield of hydrolyzed products of raw materials was 28%.

Embodiment 3

[0059] Replacement catalyst is Cu(MeCN) 4 PF 6 , the reaction time is 44h until the raw materials are completely consumed, and the rest of the conditions are the same as in Example 1. The NMR yield of III-1 is 14%, and the hydrolyzed product yield of raw materials is less than 1%.

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Abstract

The invention discloses a preparation method of a 2,3-disubstituted indoline compound, as well as a preparation method and application thereof. A tert-butyl sulfonyl (Bus) protected imine-alkyne aminecompound shown as a formula I and aryl boronic acid are used as raw materials; according to the preparation method, high-regioselectivity arylation cyclization is realized under mild reaction conditions in the presence of a cheap copper catalyst, and various 2,3-disubstituted indoline compounds are conveniently prepared at medium to excellent yield, and have a wide substrate application range andgroup tolerance. The 2,3-disubstituted indoline compound can be conveniently made into various useful 2-benzyl-1H-indole compounds and indolyl methanol compounds.

Description

technical field [0001] The application belongs to the technical field of organic synthesis methodology, and specifically relates to a 2,3-disubstituted indoline compound and its preparation method and application. Background technique [0002] Transition metal-catalyzed carbometallation / cyclization tandem reactions of alkyne compounds with unsaturated organoboronic acids have been one of the effective strategies in the field of organic synthesis for the rapid construction of complex heterocyclic / carbocyclic molecular structures. However, compared with alkyne substrates containing carbonyl structural units, transition metal-catalyzed arylation and cyclization of imine-containing alkyne substrates is rarely reported, and this type of arylation cyclization reaction is often limited Noble metal catalysts such as rhodium (Rh) and palladium (Pd), or based on the gem dimethyl effect (Thorpe-Ingoldeffect) can only use specific reaction substrates such as 2-iminoaryl boronic acid com...

Claims

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Application Information

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IPC IPC(8): C07D209/40C07D209/08C07D209/12
CPCC07D209/08C07D209/12C07D209/40Y02P20/55
Inventor 钱鹏程叶龙武
Owner INST OF NEW MATERIALS & IND TECH WENZHOU UNIV
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