CN103012238A - Preparation method of N-substituted-1H-pyrrole - Google Patents

Preparation method of N-substituted-1H-pyrrole Download PDF

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CN103012238A
CN103012238A CN201310011037XA CN201310011037A CN103012238A CN 103012238 A CN103012238 A CN 103012238A CN 201310011037X A CN201310011037X A CN 201310011037XA CN 201310011037 A CN201310011037 A CN 201310011037A CN 103012238 A CN103012238 A CN 103012238A
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yuan
replacement
aromatic
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methyl
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虞心红
翟民
杨丛斌
朱虹
刘霜
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East China University of Science and Technology
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Abstract

The invention relates to a method for preparing N-substituted-1H-pyrrole. N-substituted- 4-benzoyloxyproline used as a raw material is subjected to oxidative decarboxylation aromatization under the action of an oxidizer in a system using metal as a catalyst and amine as a ligand, thereby generating the target compound N-substituted-1H-pyrrole. The method provided by the invention has the advantages of cheap and accessible raw material, novel method, high efficiency and the like.

Description

A kind of N-replacement-1H-pyrroles's preparation method
Technical field
The present invention relates to a kind of method for preparing pyrrole derivative, specifically, relate to a kind of preparation method of N-replacement-1H-pyrrole derivative.
Background technology
The multiple biological activitys such as it is antibiotic, antiviral, antitumor that azole compounds has, the natural compounds holder Buddhist nun porphyrins with antitumour activity namely is pyrrole derivative.In recent years, find that N-(arylmethyl) azoles is to HIV-lgp41 inhibited (J.Med.Chem., 2008,5:7843-7854; Bioorg.Med.Chem., 2008,16:3039-3048), in many natural crossing cyclic cpdss and functional material, also contain this class formation (JOrg.Chem., 2001,66:550-556; J.Org.Chem.2001,66:4058-4061).
The preparation of N-aryl-pyrrolidine usually by the pyrroles in tetrahydrofuran (THF) or ionic liquid at Na, K, or the lower dehydrogenation of n-BuLi effect and equimolar halohydrocarbons reaction.
Figure BSA00000839880500011
The Pall-Knoor method is by primary amine and Isosorbide-5-Nitrae-dicarbonyl compound reaction preparation pyrrole derivative.Improved Pall-Knoor method makes N-(arylmethyl) azole compounds by benzylamine and the reaction of 2,5-dimethoxy-tetrahydrofuran:
Figure BSA00000839880500012
Primary amine and 2,5-dimethoxy-tetrahydrofuran one-step synthesis N-(arylmethyl)-pyrroles, gained N-(p-nitrophenyl methyl) pyrroles's yield 94%, N-(to the cyano group phenmethyl) pyrroles's yield 44% (J.Org.Chem., 1998,63:6715-6718); Change in the tetrahydrofuran aqueous solution and react, seven aqueous ferric chloride catalysis, 60 ℃ of reaction 104h, N-(phenmethyl) pyrroles yield 78% (Synlett, 2009, (14): 2245-2248); Primary amine and 2,5-dimethoxy-tetrahydrofuran reflux can get N-phenmethyl pyrroles in one hour, yield 64% (Bioorganic ﹠amp; Medicinal Chemistry Letters.2008,18 (15): 4325-4327).
With N-allyl group-N-benzyl third-2-alkene-1-amine at Grubbs catalyzer and RuCl 3Under the combined action, react 12h under 60 ℃ of ultrasonic wave, obtain N-(phenmethyl) pyrroles, yield is 55% (Tetrahedron Letters.2004,45:8995-8998) only.
Benzylamine and Isosorbide-5-Nitrae-two chloro-Isosorbide-5-Nitrae-dimethoxy-butanes react in methylene dichloride and have obtained N-(phenmethyl) pyrroles, and yield 90% (J.Org.Chem., 1983,48:3059-3061);
Figure BSA00000839880500022
Benzylamine and 2-chlorine ring the third formaldehyde react N-(phenmethyl) pyrroles (Zhurnal Organicheskoi Khimii, 1991,27 (8): 1621-1625) that obtained yield 89% in DMF;
Figure BSA00000839880500023
Adopt 3-pyrroline and aromatic aldehyde compound under phenylformic acid catalysis, reflux in toluene reaction 6-12h, N-hydrocarbonylation-aromizing obtains N-(arylmethyl) pyrroles, yield 70-90% (J.Am.Chem.Soc., 2009,131:16626-16627);
Figure BSA00000839880500024
N-(arylmethyl)-Pyrrolidine can be oxidized to N-(arylmethyl) pyrroles in the aqueous solution and under beta-cyclodextrin and the effect of 2-iodoxybenzene formic acid, yield 86% (Tetrahedron Letters.2011,52 (34), 4481-4484).
Figure BSA00000839880500025
Used Isosorbide-5-Nitrae-two in the aforesaid method-(dimethylamino)-1,3-butadiene, 1,4-two chloro-1, the prices such as 4-dimethoxy-butane, 2-chlorine ring the third formaldehyde, 3-pyrroline are expensive and be difficult to obtain, and pyrroles and the 3-pyrroles raw material of etc.ing is unstable, and need react under inert conditions.
Chinese invention patent (CN 102180824 A) disclosed a kind of aromatic aldehyde and CHP under phenylformic acid catalysis at N, synthetic N-(arylmethyl) pyrroles's of back flow reaction method in the dinethylformamide, yield 84%, but the solubleness of CHP in DMF is not high, produce easily side reaction because aldehyde is excessive, need to be heated to 140 ℃, slowly drip aromatic aldehyde and react complex operation.
Figure BSA00000839880500031
Summary of the invention
The object of the invention is to, a kind of novel, method that efficiently oxidation prepares the N-substituted azole derivatives is provided.
The present invention's N-substituted azole derivatives to be prepared, its structural formula is suc as formula shown in the I:
Figure BSA00000839880500032
Among the formula I, Ar is 5～6 yuan of aromatic ring yls of 5～6 yuan of aromatic ring yls, 5～6 yuan of aromatic heterocyclics, replacement;
Wherein, the heteroatoms of said aromatic heterocyclic is selected from: a kind of among N, O or the S, and the heteroatoms number is 1～3 integer;
The substituting group of 5～6 yuan of aromatic ring yls of said replacement or 5～6 yuan of aromatic heterocyclics of replacement is selected from: in halogen, nitro, trifluoromethyl, cyano group or the alkoxyl group one or more.
The method of compound shown in the preparation provided by the present invention; its key step is: catalyzer and part react 10min under the room temperature under protection of inert gas in toluene after; compound shown in the structural formula II and oxygenant are added in the reaction medium; in 110 ℃ of reactions, make target compound (compound shown in the formula I).
Figure BSA00000839880500033
Among the formula II, the definition of Ar is identical with preamble.
Specific implementation method
In the preferred technical solution of the present invention, said catalyzer is (but being not limited to) FeSO 4.7H 2O, CuBr, FeCl 3
Preferred catalyzer is FeSO 4.7H 2O;
In a further preferred technical solution of the present invention, said reaction medium is toluene, dimethylbenzene, water, acetone, Isosorbide-5-Nitrae-dioxane, DMF, N,N-dimethylacetamide, methyl-sulphoxide or tetramethylene sulfone etc.;
In a further preferred technical solution of the present invention, used oxygenant is 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone, tertbutyl peroxide, di-t-butyl peroxide, 2-iodoxybenzene formic acid;
Preferred oxygenant is di-t-butyl peroxide;
In a further preferred technical solution of the present invention, part is triethylamine, triethylene diamine, N, N-dimethyl-ethylenediamine, beta-cyclodextrin;
Preferred part is N, the N-dimethyl-ethylenediamine;
In a further preferred technical solution of the present invention, the mol ratio of Compound I I and catalyzer, oxygenant, part is: 1: 0.1～0.4: 1～1.5: 0.1～0.5;
Preferred mol ratio is: 1: 0.15: 1.4: 0.3;
The solvent of recommendation of the present invention is toluene;
The suggestion consumption of described organic solvent is 10 milliliters～20 ml/gs .4-benzoyloxys-N-substituted azole quinoline-2-carboxylic acid, and namely every gram 4-benzoyloxy N-substituted azole quinoline-2-carboxylic acid (compound shown in the formula II) needs with 10 milliliters～20 milliliters described organic solvents;
In a further preferred technical solution of the present invention, Ar is the hexa-atomic aromatic ring yl of hexa-atomic aromatic ring yl, five yuan of aromatic heterocyclics or replacement;
Wherein, the substituting group of the hexa-atomic aromatic heterocyclic of said replacement is selected from S or O, and number of heteroatoms is 1～2 integer;
The substituting group of the hexa-atomic aromatic ring yl of said replacement is selected from: one or more in methyl, nitro, cyano group, trifluoromethyl or the methoxyl group.
Below by embodiment the present invention is further set forth, purpose only is better to understand content of the present invention.Therefore, listed protection scope of the present invention that do not limit:
Embodiment 1 N-phenmethyl-1H-pyrroles's preparation
Figure BSA00000839880500041
FeSO 4.7H 2O (0.021g, 0.15mmol), N, N-dimethyl-ethylenediamine (0.027g, 0.3mmol) be suspended in 10 milliliters of toluene, stirring at room 10min, rear adding 4-(benzoyloxy)-1-benzyl-tetramethyleneimine-2-carboxylic acid (0.33g, 1mmol), di-t-butyl peroxide (0.2g, 1.4mmol), back flow reaction is spent the night, and desolventizing is revolved in the reaction solution decompression, and silica gel column chromatography (washing and dehydrating integrated machine is petrol ether/ethyl acetate=10: 1 (v/v)) obtains N-phenmethyl-1H-pyrroles 0.10g, colourless liquid, yield 64%; 1HNMR (400MHz, CDCl 3) δ ppm5.18 (s, 2H), 6.36 (t, J=2.01,2.01Hz, 2H), 6.84 (t, J=1.99,1.99Hz, 2H), 7.26 (d, J=7.08Hz, 2H), 7.45 (m, 3H); 13C NMR (101MHz, CDC1 3) δ ppm 53.43,108.68,121.30,127.14,127.77,128.86,138.371; MS, m/z (relative intensity): 157.1 (69.8), 91.1 (100), 158.1 (7.7), 156.1 (8.3), 92.1 (6.5).
Embodiment 2 N-phenmethyl-1H-pyrroles's preparation
Except replacing FeSO with CuBr (0.022g, 0.15mmol) 4.7H 2Outside the O (0.021g, 0.15mmol), the other the same as in Example 1 obtains N-phenmethyl-1H-pyrroles 0.10g, colourless liquid, yield 62%; 1H NMR (400MHz, CDC1 3) δ ppm5.18 (s, 2H), 6.36 (t, J=2.01,2.01Hz, 2H), 6.84 (t, J=1.99,1.99Hz, 2H), 7.26 (d, J=7.08Hz, 2H), 7.45 (m, 3H); 13C NMR (101MHz, CDC1 3) δ ppm 53.43,108.68,121.30,127.14,127.77,128.86,138.371; MS, m/z (relative intensity): 157.1 (69.8), 91.1 (100), 158.1,7.7), 156.1 (8.3), 92.1 (6.5).
Embodiment 3 N-(4-trifluoromethyl-phenmethyl)-1H-pyrroles's preparation
Figure BSA00000839880500052
Except with 4-(benzoyloxy)-1-(4-(trifluoromethyl)-benzyl) tetramethyleneimine-2-carboxylic acid (0.39g, 1mmol) replace 4-(benzoyloxy)-1-(4-benzyl) tetramethyleneimine-2-carboxylic acid (0.33g, 1mmol), the other the same as in Example 1, obtain N-(4-trifluoromethyl-phenmethyl)-1H-pyrroles 0.14g, yellow liquid, yield 63%; 1NMR (400MHz, CDCl 3) δ ppm 5.19 (s, 2H), 6.31 (s, 2H), 6.76 (s, 2H), 7.25 (d, J=7.96Hz, 2H), 7.64 (d, J=7.97Hz, 2H); 13C NMR (101MHz, CDC1 3) δ ppm 52.80,109.10,121.24,125.74 (q, J=3.77,3.75,3.75Hz, 1C), 127.10,142.43; ESI for[M+H]: calculated, 226.0844; Found, 226.0843.
Embodiment 4 N-(3,5-dimethoxy-phenmethyl)-1H-pyrroles's preparation
Figure BSA00000839880500061
Except with 4-(benzoyloxy)-1-(2,5-dimethoxy-benzyl) tetramethyleneimine-2-carboxylic acid (0.37g, 1mmol) replace 4-(benzoyloxy)-1-(4-benzyl) tetramethyleneimine-2-carboxylic acid (0.33g, 1mmol), the other the same as in Example 1 obtains N-(3,5-dimethoxy-phenmethyl)-1H-pyrroles 0.117g, colourless liquid, yield 54%; 1NMR (400MHz, CDCl 3) δ ppm 3.78 (s, 6H), 5.04 (s, 2H), 6.23 (t, J=2.02,2.02Hz, 2H), 6.30 (d, J=2.02Hz, 2H), 6.41 (t, J=2.09,2.09Hz, 1H), 6.73 (t, J=1.97,1.97Hz, 2H); 13C NMR (101MHz, CDCl 3) δ ppm53.39,55.32,99.40,105.07,108.55,121.24,140.62,161.15; ESI for[M+H]: calculated, 218.1181; Found, 218.1182.
Embodiment 5 N-(4-nitro-phenmethyl)-1H-pyrroles's preparation
Figure BSA00000839880500062
Except with 4-(benzoyloxy)-1-(4-nitro-benzyl) tetramethyleneimine-2-carboxylic acid (0.37g, 1mmol) replace 4-(benzoyloxy)-1-(4-benzyl) tetramethyleneimine-2-carboxylic acid (0.33g, 1mmol), the other the same as in Example 1, obtain N-(3,5-dimethoxy-phenmethyl)-and 1H-pyrroles 0.15g, yellow solid, yield 76%; 1HNMR (400MHz, CDCl 3) δ: 8.17 (2H, d, J=8.67Hz), 7.20 (2H, d, J=8.57Hz), 6.70 (2H, t, J=1.97,1.97Hz), 6.25 (2H, t, J=1.99,1.99Hz), 5.19 (2H, s); 13C NMR (101MHz, CDC1 3) δ: 147.46,145.76,127.38,124.02,121.26,109.41,52.56; MS, m/z (relative intensity): 122.1 (100), 103.1 (10.0), 201.1 (28.5), 156.1 (10.7), 155.1 (7.2), 154.1 (7.4), 136.0 (23.5), 128.1 (5.8), 127.1 (4.1), 106.0 (23.2), 90.0 (15.9) 89.0 (21.5), 78.0
Embodiment 6 N-phenmethyl-1H-pyrroles's preparation
Figure BSA00000839880500071
Except with tertbutyl peroxide (0.13g, 1.4mmol) and triethylamine (0.027g, 0.3mmol), replace di-t-butyl peroxide (0.2g, 1.4mmol) and N, N-dimethyl-ethylenediamine (0.027g, 0.3mmol) outside, the other the same as in Example 2 obtains N-phenmethyl-1H-pyrroles 0.10g, colourless liquid, yield 59%; 1H NMR (400MHz, CDCl 3) δ ppm5.18 (s, 2H), 6.36 (t, J=2.01,2.01Hz, 2H), 6.84 (t, J=1.99,1.99Hz, 2H), 7.26 (d, J=7.08Hz, 2H), 7.45 (m, 3H); 13C NMR (101MHz, CDCl 3) δ ppm 53.43,108.68,121.30,127.14,127.77,128.86,138.371; MS, m/z (relative intensity): 157.1 (69.8), 91.1 (100), 158.1 (7.7), 156.1 (8.3), 92.1 (6.5).
Embodiment 7 N-phenmethyl-1H-pyrroles's preparation
Figure BSA00000839880500072
Except with tertbutyl peroxide (0.13g, 1.4mmol) and triethylene diamine (0.04g, 0.3mmol) replacement di-t-butyl peroxide (0.2g, 1.4mmol) and N, outside the N-dimethyl-ethylenediamine (0.027g, 0.3mmol), the other the same as in Example 2, obtain N-phenmethyl-1H-pyrroles 0.08g, colourless liquid, yield 48%; 1HNMR (400MHz, CDCl 3) δ ppm5.18 (s, 2H), 6.36 (t, J=2.01,2.01Hz, 2H), 6.84 (t, J=1.99,1.99Hz, 2H), 7.26 (d, J=7.08Hz, 2H), 7.45 (m, 3H); 13C NMR (101MHz, CDCl 3) δ ppm 53.43,108.68,121.30,127.14,127.77,128.86,138.371; MS, m/z (relative intensity): 157.1 (69.8), 91.1 (100), 158.1,7.7), 156.1 (8.3), 92.1 (6.5).
Embodiment 8 N-phenmethyl-1H-pyrroles's preparation
Figure BSA00000839880500081
Except with FeCl 3(0.024g, 0.15mmol) replaces outside the CuBr (0.022g, 0.15mmol), and other arrives N-phenmethyl-1H-pyrroles 0.08g, colourless liquid, yield 48% with embodiment 7; 1HNMR (400MHz, CDC1 3) δ ppm5.18 (s, 2H), 6.36 (t, J=2.01,2.01Hz, 2H), 6.84 (t, J=1.99,1.99Hz, 2H), 7.26 (d, J=7.08Hz, 2H), 7.45 (m, 3H); 13C NMR (101MHz, CDC1 3) δ ppm 53.43,108.68,121.30,127.14,127.77,128.86,138.371; MS, m/z (relative intensity): 157.1 (69.8), 91.1 (100), 158.1 (7.7), 156.1 (8.3), 921 (65).

Claims (9)

1. method for preparing suc as formula compound shown in the I, its key step is: in the presence of catalyzer and oxygenant, in reaction medium, 100 ℃ of-140 ℃ of reactions make target compound I by compound shown in the formula II:
Figure FSA00000839880400011
Wherein, Ar is 5～6 yuan of aromatic ring yls of 5～6 yuan of fragrant heterocycles, 5～6 yuan of aromatic heterocyclics, replacement or 5～6 yuan of aromatic heterocyclics of replacement; The heteroatoms of said aromatic heterocyclic is: among N, O or the S one or more, the heteroatoms number is 1～3 integer;
The substituting group of 5～6 yuan of aromatic ring yls of said replacement or 5～6 yuan of aromatic heterocyclics of replacement is: in halogen, nitro, trifluoromethyl, cyano group or the alkoxyl group one or more.
2. the method for claim 1 is characterized in that, used oxygenant is DDQ, TBHP, DTBP.
3. the method for claim 1 is characterized in that, used catalyzer is FeSO 4.7H 2O, CuBr, IBX, FeCl 3.。
4. the method for claim 1 is characterized in that, used part is TEA, DABCO, TEMED, β-CD.
5. the method for claim 1 is characterized in that, the mol ratio of Compound I I and catalyzer, oxygenant, part is: 1: 0.1～0.4: 1～1.5: 0.1～0.5.
6. the method for claim 1 is characterized in that, wherein said organic solvent is: toluene, dimethylbenzene, water, acetone, Isosorbide-5-Nitrae-dioxane, DMF, N,N-dimethylacetamide, methyl-sulphoxide or tetramethylene sulfone.
7. such as the described method of any one in the claim 1～6, it is characterized in that wherein Ar is 6 yuan of aromatic ring yls, 5 yuan of aromatic heterocyclics or 6 yuan of aromatic ring yls of replacement, 6 yuan of aromatic heterocyclics;
Wherein, the heteroatoms of said aromatic heterocyclic is S or O, and the method for claim 1 is characterized in that, atomicity wherein is 1～2 integer;
The substituting group of 6 yuan of aromatic heterocyclics of said replacement is selected in: one or more in methyl, nitro, cyano group, trifluoromethyl, the methyl or methoxy.
8. method as claimed in claim 7 is characterized in that, wherein Ar is the phenyl of phenyl, furyl, thienyl, pyridyl or replacement;
The substituting group of the phenyl of said replacement is selected in: one or more in methyl, nitro, cyano group, trifluoromethyl or the methoxyl group.
9. method claimed in claim 7 is characterized in that, wherein Ar is phenyl, 4-methyl, 4-nitro, 4-cyano group, 4-trifluoromethyl, 2-cyano group, 3,5-dimethoxy, 3-nitro, 4-methoxyl group, 2-furyl, 2-thienyl, 2-pyridyl.
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CN113788778A (en) * 2021-10-09 2021-12-14 河北威远生物化工有限公司 Aromatizing method of nitrogen-containing heterocyclic compound
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Application publication date: 20130403