Indole eight-membered middle-ring compound and preparation method thereof

A ring compound and compound technology, applied in the field of indolo eight-membered ring compound and its preparation, can solve the problems of severe reaction conditions, complex synthesis of raw materials, limited substrates, etc., and achieve the effect of mild conditions and simple operation

Inactive Publication Date: 2021-07-16
QINGDAO AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, in order to overcome the problems in the prior art and obtain a better reaction path for mesocyclic compounds, to improve the existing problems of severe reaction conditions, complex raw material synthesis, and limited substrates

Method used

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  • Indole eight-membered middle-ring compound and preparation method thereof
  • Indole eight-membered middle-ring compound and preparation method thereof
  • Indole eight-membered middle-ring compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071]

[0072] White solid; 30.2mg, 95% yield; mp 192-194°C; column chromatography yeluent, petroleum ether / EtOAc=250:1; 1 H NMR (500MHz, CDCl 3 )δ7.43(d, J=8.0Hz, 1H), 7.10(d, J=8.2Hz, 1H), 7.05-7.00(m, 1H), 6.96-6.91(m, 1H), 6.85-6.81(m ,2H),6.76-6.68(m,2H),5.45(dd,J=8.2,6.6Hz,1H),5.14(d,J=14.5Hz,1H),4.16(d,J=14.5Hz,1H) ,3.54(s,3H),3.42-3.32(m,1H),3.17-3.08(m,1H),2.92(s,3H),2.46-2.36(m,1H),2.36-2.28(m,1H) ,2.20-2.01(m,2H); 13 CNMR (125MHz, CDCl 3 )δ144.00,143.26,137.08,135.03,126.09,122.96,122.14,120.93,120.80,120.65,118.93(2C),114.01,109.11,60.88,52.71,50.91,44.20,31.28,29.43,24.02;HRMS(ESI-TOF) m / z calcd for C 21 h 24 N 3 [M+H] + :318.1965; found: 318.1967.

Embodiment 2

[0074]

[0075] Colorless oil; 28.7mg, 83% yield; column chromatography eluent, petroleummether / EtOAc=250:1; 1 H NMR (500MHz, CDCl 3 )δ7.45(d, J=7.8Hz, 1H), 7.02(d, J=7.9Hz, 1H), 6.98(t, J=7.4Hz, 1H), 6.93(t, J=7.3Hz, 1H) ,6.82(d,J=7.7Hz,1H),6.78-6.70(m,2H),6.68-6.61(m,1H),5.80-5.69(m,1H),5.65(t,J=7.5Hz,1H ),4.89(d,J=10.0Hz,1H),4.82(d,J=14.5Hz,1H),4.53(s,2H),4.38(d,J=17.5Hz,1H),4.13(d,J =14.0Hz,1H),3.41-3.31(m,1H),3.15-3.04(m,1H),2.85(s,3H),2.47-2,36(m,2H),2.20-2.02(m,2H ); 13 CNMR (125MHz, CDCl 3 )δ144.10,143.37,136.56,135.07,133.08,126.30,123.64,121.80,121.45,120.91,119.84,119.16,119.14,116.35,114.10,109.42,60.16,53.22,50.69,44.97,44.25,30.62,24.02;HRMS(ESI -TOF)m / zcalcd for C 23 h 26 N 3 [M+H] + :344.2121; found: 344.2122.

Embodiment 3

[0077]

[0078] Yellow solid; 35.0mg, 89% yield; mp 90-92°C; column chromatography yeluent, petroleum ether / EtOAc=200:1; 1 H NMR (500MHz, CDCl 3 )δ7.51-7.45(m,1H),7.12-7.05(m,3H),6.99(dt,J=6.2,3.3Hz,1H),6.97-6.92(m,2H),6.75(qd,J= 8.2,4.2Hz,2H),6.67(dd,J=10.0,4.5Hz,2H),6.63(dd,J=7.4,1.4Hz,2H),5.67(t,J=7.5Hz,1H),5.18( s,2H),4.85(d,J=14.0Hz,1H),4.12(d,J=14.0Hz,1H),3.43–3.32(m,1H),3.17-3.07(m,1H),2.69(s ,3H),2.48-2.40(m,2H),2.23-2.04(m,2H); 13 C NMR (125MHz, CDCl 3 )δ143.98,143.34,137.75,136.83,135.05,128.80(2C),127.17,126.38,125.86(2C),123.56,121.86,121.59,121.10,119.96,119.31,119.15,114.37,109.56,60.23,53.25,50.75,46.23 ,44.04,30.65,23.98; HRMS(ESI-TOF)m / z calcd for C 27 h 28 N 3 [M+H] + :394.2278; found: 394.2277.

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Abstract

The invention discloses an indole eight-membered middle-ring compound and a preparation method thereof, which belong to the technical field of organic synthesis. Indole-2-formaldehyde and N-substituted aniline are subjected to an in-situ reaction to initiate [1, 6]-HT, and generated high-activity imine positive ions and electronegative indole C-3 are subjected to a Friedel-Crafts reaction to synthesize the indole diaza eight-membered fused ring compound. The reaction has the advantages of simple and easily available raw materials, strong universality, mild reaction conditions, good chemical selectivity, high product yield and the like.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to an indolo eight-membered mesocyclic compound and a preparation method thereof. Background technique [0002] Mesocyclic compounds widely exist in many natural products, drug molecules and functional molecules, most of which have important pharmacological and physiological activities. An example is the antihypertensive drug Benazepril. The special conformation of the middle ring structure can not only enhance the binding degree of functional groups to biological targets, but also improve bioavailability and enhance cell permeability, such as related literature (J.Am.Chem.Soc.2006, 128, 2510; Chem.Biol. 2007,14,671; J.Med.Chem.2002,45,2615 and Nat.Chem.Biol.2013,9,21) introduced the role of mesocyclic compounds in cell permeability. [0003] Among many active molecules, indole or benzo eight / nine-membered aza skeletons are particularly common. For example, ...

Claims

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Application Information

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IPC IPC(8): C07D487/14A01N43/90A01P7/02
CPCC07D487/14A01N43/90
Inventor 肖建邱斌王琳璇
Owner QINGDAO AGRI UNIV
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