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Method for synthesizing dihydrogen phenanthridine

A synthesis method and a technology for dihydrophenanthridine, applied in the field of synthesizing dihydrophenanthridine, can solve the problems of not having too many effective methods for obtaining this type of compound, and achieve the effects of high yield and few reaction steps.

Inactive Publication Date: 2013-03-06
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] However, so far, there are not many effective methods for obtaining such compounds

Method used

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  • Method for synthesizing dihydrogen phenanthridine
  • Method for synthesizing dihydrogen phenanthridine
  • Method for synthesizing dihydrogen phenanthridine

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Embodiment 1: the synthesis of compound (2a)

[0028]

[0029] Phenanthridine 1a (36mg, 0.20mmol) and [Ru(p-cymene)I 2 ] 2 (2.0 mg, 0.002 mmol) was dissolved in 2 mL of dichloromethane. After stirring at room temperature for 10 min, the reaction system was transferred to an autoclave and filled with hydrogen (40 atm). After stirring the reaction at room temperature for 24 h, the remaining hydrogen was carefully released, and column chromatography gave dihydrophenanthridine 2a, 35 mg of white solid, yield 97%, mp 100-102 °C, 1 H NMR (400MHz, CDCl 3 )δ7.64-7.72 (m, 2H), 7.31 (t, J = 7.8Hz, 1H), 7.21 (td, J = 7.4, 1.1Hz, 1H), 7.10 (td, J = 7.8, 1.2Hz, 2H ), 6.84(td, J=7.7, 1.1Hz, 1H), 6.67(dd, J=7.9, 0.9Hz, 1H), 4.40(s, 2H). 13 C NMR (100MHz, CDCl 3 )δ 145.6, 132.6, 131.9, 128.7, 127.5, 127.0, 125.9, 123.4, 122.3, 121.8, 119.1, 115.0, 46.2.

Embodiment 2

[0030] Embodiment 2: the synthesis of compound (2b)

[0031]

[0032] Phenanthridine 1b (39mg, 0.20mmol) and [Ru(p-cymene)I 2 ] 2 (2.0 mg, 0.002 mmol) was dissolved in 2 mL of dichloromethane. After stirring at room temperature for 10 min, the reaction system was transferred to an autoclave and filled with hydrogen (40 atm). After stirring the reaction at room temperature for 24 hours, the remaining hydrogen was carefully released, and column chromatography gave dihydrophenanthridine 2b, 37 mg of white solid, yield 95%, mp 87-89 °C, 1 H NMR (400MHz, CDCl 3 )δ7.65-7.76(m, 2H), 7.20-7.35(m, 2H), 7.09-7.16(m, 2H), 6.83(t, J=7.4Hz, 1H), 6.66(t, J=9.4Hz , 1H).4.55(q, J=6.3Hz, 1H), 3.95(s, 1H), 1.44(d, J=6.4Hz, 3H). 13 C NMR (100MHz, CDCl 3 )δ 146.6, 133.6, 131.9, 128.9, 127.5, 127.0, 125.9, 124.1, 122.5, 122.2, 119.4, 115.3, 60.2, 21.6.

Embodiment 3

[0033] Embodiment 3: the synthesis of compound (2c)

[0034]

[0035] Phenanthridine 1c (51mg, 0.20mmol) and [Ru(p-cymene)I 2 ] 2 (2.0 mg, 0.002 mmol) was dissolved in 2 mL of dichloromethane. After stirring at room temperature for 10 min, the reaction system was transferred to an autoclave and filled with hydrogen (60 atm). After stirring and reacting at 50°C for 24h, the remaining hydrogen was carefully released, and column chromatography gave dihydrophenanthridine 2c, 48 mg of white solid, 94% yield, mp111-113°C, 1 H NMR (400MHz, CDCl 3 )δ7.67-7.82(m, 3H), 7.28-7.44(m, 5H), 7.13(q, J=8.0Hz, 2H), 6.85(t, J=7.5Hz, 1H), 6.79(d, J =7.6Hz, 1H), 6.64(d, J=7.9Hz, 1H), 4.28(s, 1H). 13C NMR (100MHz, CDCl 3 )δ 146.6, 142.6, 141.7, 133.6, 131.9, 129.3, 129.1, 128.9, 128.7, 128.1, 127.5, 127.0, 125.9, 124.1, 122.5, 122.2, 119.4, 115.3, 66.9.

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Abstract

The invention relates to a method for synthesizing dihydrogen phenanthridine. According to the invention, transition metals [Ru (II), Rh (I), and Ir (I)] are adopted as catalyst for realizing phenanthridine catalytic hydrogenation. Also, according to the invention, 9,10-dihydrogen phenanthridine in-situ regeneration is applied in asymmetric transfer hydrogenation of unsaturated imine. Only a catalytic amount of phenanthridine is needed to be added, and chiral amine can be synthesized with high enantioselectivity.

Description

technical field [0001] The invention relates to a method for synthesizing dihydrophenanthridine. Background technique [0002] 9,10-dihydrophenanthridine and its derivatives are not only an important class of organic synthesis intermediates, but also the structural units of many phenanthridine alkaloids with physiological activity, so they have attracted widespread attention. (Reference 1: (a) Harayama, T.; Akiyama, T.; Akamatsu, H.; Kawano, K.; Abe, H.; Takeuchi, Y. Synthesis 2001, 2001, 444; (b) Donaldson, L.R. ; Haigh, D.; Hulme, A.N. Tetrahedron 2008, 64, 4468; (c) Yang, C.-H.; Cheng, M.-J.; .-J.; Chen, I.-S.J.Nat.Prod.2008, 71, 669.) For example, the compound Lycorine (lycorine) has a strong emetic effect and can be used as a substitute for ipecac, which is stronger than emetine. Not as good as apomorphine, which is less toxic; it has an expectorant effect. Betaine salts made from lycorine showed antitumor effects in animals. Compound Chelidonine (chelidonine) can b...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/12C07D265/36
Inventor 周永贵陈庆安高凯时磊余长斌
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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