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Method for preparing allyl indole compounds by 1,4-difunctionalization reaction of olefin

An allyl indole and compound technology, which is applied in the field of preparing allyl indole compounds by 1,4-difunctionalization reaction of olefins, can solve the problem of harsh process conditions, high reaction cost, difficult source of starting materials, etc. question

Active Publication Date: 2018-11-30
NANCHANG HANGKONG UNIVERSITY
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  • Application Information

AI Technical Summary

Problems solved by technology

However, these methods require the use of expensive gold / silver / organic ligand catalytic systems, and / or the design of complex reaction starting materials to be realized, and there are defects such as harsh process conditions, difficult sources of starting materials, and high reaction costs.

Method used

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  • Method for preparing allyl indole compounds by 1,4-difunctionalization reaction of olefin
  • Method for preparing allyl indole compounds by 1,4-difunctionalization reaction of olefin
  • Method for preparing allyl indole compounds by 1,4-difunctionalization reaction of olefin

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Experimental program
Comparison scheme
Effect test

Embodiment 19

[0066]

[0067] The compound of formula II-2 was used as the raw material, and the rest of the reaction raw materials, operations and parameters were the same as in Example 1 to obtain the target product IV-2 with a yield of 86%; 1 H NMR (500MHz, CDCl 3 )δ: 7.27(d, J=7.5Hz, 1H), 7.23(d, J=9.5Hz, 1H), 7.16(d, J=7.5Hz, 2H), 7.10(t, J=7.5Hz, 1H) ,6.94(t,J=7.3Hz,1H),6.78-6.76(m,2H),6.11-6.06(m,1H),5.44-5.38(m,1H),4.88(d,J=7.5Hz,1H ),4.06-3.99(m,2H),3.75(s,3H),3.65(s,3H),2.51(d,J=7.0Hz,2H),2.42-2.39(m,2H),2.31(s, 3H), 1.92-1.82(m, 4H), 1.15-1.12(m, 3H); 13 CNMR (125MHz, CDCl 3 )δ: 176.9, 157.7, 136.7, 135.9, 135.3, 133.1, 129.0, 126.8, 125.9, 120.3, 119.5, 118.5, 113.4, 112.7, 108.5, 60.2, 55.2, 47.4, 44.3, 40.6, 13, 41.5, 29. , 10.6.

Embodiment 20

[0069]

[0070] Using the compound of formula II-a as the raw material, the rest of the reaction raw materials, operations and parameters are the same as in Example 1 to obtain the target product IV-3 with a yield of 65%; 1 H NMR (500MHz, CDCl 3 )δ: 7.23(t, J=8.3Hz, 2H), 7.11(t, J=8.0Hz, 3H), 6.95(t, J=7.5Hz, 1H), 6.79(d, J=8.5Hz, 2H) ,6.19-6.14(m,1H),5.25-5.19(m,1H),4.92(d,J=6.0Hz,2H),4.65(d,J=6.0Hz,1H),4.62-4.57(m,2H ),3.78-3.73(m,5H),3.65(s,3H),2.49(d,J=7.5Hz,2H),2.30(s,3H); 13 C NMR (125MHz, CDCl 3 )δ: 157.8, 139.6, 136.7, 134.7, 133.3, 128.9, 126.5, 120.4, 119.9, 119.2, 118.7, 113.54, 111.5, 108.7, 93.7, 85.6, 70.2, 55.2, 44.0, 36.8, 26.5, 10.

Embodiment 21

[0072]

[0073] Using the compound of formula II-3 as the raw material, the rest of the reaction raw materials, operations and parameters were the same as in Example 1 to obtain the target product IV-4 with a yield of 66%; 1 H NMR (500MHz, CDCl 3 )δ: 7.27-7.22(m, 2H), 7.15(d, J=8.5Hz, 2H), 7.10(t, J=7.5Hz, 1H), 6.94(t, J=7.5Hz, 1H), 6.77( d,J=9.0Hz,2H),6.17-6.12(m,1H),5.48-5.42(m,1H),4.88(d,J=7.5Hz,1H),4.18-4.07(m,4H),3.75 (s,3H),3.65(s,3H),3.41(t,J=7.5Hz,1H),2.66(t,J=7.3Hz,2H),2.30(s,3H),1.22-1.16(m, 6H); 13 C NMR (125MHz, CDCl 3 )δ: 169.0, 157.7, 136.7, 135.7, 135.4, 133.1, 128.9, 126.7, 126.1, 120.3, 119.4, 118.6, 113.4, 112.4, 108.5, 61.3, 55.2, 52.1, 44.1, 31.7, 20, 10.6, 14.6

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Abstract

The invention discloses a synthetic method for preparing allyl indole compounds. A conjugated diene compound represented by formula I, a compound represented by formula II and indole compounds represented by formula III are used as reaction raw materials, an indium catalyst, Ag2CO3 and an organic solvent are added, the reaction raw materials are heated, stirred and reacted under inert gas protection conditions, and post-treatment is carried out after a result of TLC or GC-MS monitoring shows that the reaction is completed in order to obtain the allyl indole compounds represented by formula IV.The method has the advantages of easily obtained sources of the raw materials, simple process route, mild reaction conditions, low process cost, wide substrate adaptation range and high target product yield.

Description

technical field [0001] The application belongs to the technical field of organic synthesis, and specifically relates to a method for preparing allyl indole compounds through 1,4-difunctionalization reaction of olefins. Background technique [0002] Unsaturated hydrocarbon compounds are important products in petrochemical and coal chemical industries, and are an important material basis of the national economy and an indispensable resource for sustainable development. The rapid increase of molecular complexity from readily available chemicals (especially feedstocks derived from the petroleum industry, such as alkenes, alkanes, and aromatics) through mild, economical, and practical selective catalytic pathways is an important topic in academia and One of the main goals of the industry. In this field, the functionalization of molecules through the transformation of olefins and / or C–H bonds is an attractive and challenging goal, which has aroused great interest among researcher...

Claims

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Application Information

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IPC IPC(8): C07D209/24C07D405/06C07D209/12C07D209/22C07D471/06
CPCC07D209/12C07D209/22C07D209/24C07D405/06C07D471/06
Inventor 李金恒宋仁杰顾昌程
Owner NANCHANG HANGKONG UNIVERSITY
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