CN110172061A - A kind of synthetic method of pyrrolo- [3,4-b] quinoline -1,8- derovatives - Google Patents
A kind of synthetic method of pyrrolo- [3,4-b] quinoline -1,8- derovatives Download PDFInfo
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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Abstract
A kind of pyrrolo- [3,4-b] quinoline -1, the synthetic method of 8- derovatives, it include: addition 0.04 mM of the aldehyde, 0.04 mM of 1- benzyl -2 in 95% ethanol solution, 4- dioxo pyrrolidin -3- carboxylic acid, ethyl ester and 0.04 mM of ketones with Enamino-esters, back flow reaction 6-8 hours is to get arriving corresponding pyrrolo- [3,4-b] quinoline -1,8- derovatives.Synthetic method of the invention, under the conditions of 95% alcohol reflux, aldehyde, 1- benzyl -2,4- dioxo pyrrolidin -3- carboxylic acid, ethyl ester have simply and efficiently synthesized pyrrolo- [3,4-b] quinoline with up to three component one kettle way of ketones with Enamino-esters derived from rice ketone.This method has the advantages such as raw material is easy to get, yield is higher, simple to operation, atom utilization is high, meets the requirement of Green Chemistry, can be used as the new way of synthesis pyrrolo- [3,4-b] quinolines.
Description
Technical field
The present invention relates to organic syntheses, and in particular to a kind of synthesis of pyrrolo- [3,4-b] quinoline -1,8- derovatives
Method.
Background technique
Pyrrolo- [3,4-b] quinoline -1,8- derovatives contain pyrrole skeleton.Pyroles skeleton is widely present in life
In alkaloids, protein, natural dye and drug molecule and chemical products (Martin, M.C., Patil, D.V., France,
S.J.Org.Chem, 2014,79 (7), 3030), some azole derivatives have bioactivity, can be used as anti-microbial type, antitumor
Class and anti-inflammatory and antalgic class drug (Di Santo, R., Costi, R., Artico, M., Bioorg.Med.Chem.Lett., 1998,
8(20),2931；Baker,E.S.,Lee,J.T.,Sessler,J.L.,Bowers,M.T.,J.Amer.Chem.Soc.,
2006,128(8),2641；Wei,W.-H.,Wang,Z.,Mizuno,T.,Cortez,C.,Fu,L.,Sirisawad,M.,
Naumovski,L.,Magda,D.,Sessler,J.L.,Dalton Trans.,2006,(16),1934；Gale,P.A.,
Tong,C.C.,Haynes,C.J.E.,Adeosun,O.,Gross,D.E.,Karnas,E.,Sedenberg,E.M.,
Quesada,R.,Sessler,J.L.,J.Amer.Chem.Soc.,2010,132(10),3240.).In addition, azole derivatives
Also there is outstanding performance in terms of pesticide, such as chlorfenapyr is exactly that a kind of good desinsection kills snail agent, can be used for various crop
The prevention and control of plant diseases, pest control (Xu Shangcheng, Jiang Mugeng, Pesticide Science journal, 2002,4 (2), 1), in addition to this, azole derivatives can also be made
For raw material be widely used in the fields such as organic synthesis, photosensitive material, rubber, epoxy resin (Sessler, J.L., Camiolo,
S.,Gale,P.A.,Coord.Chem.Rev.,2003,240(1-2),17).Therefore these two types of structural units are spliced and is tied
The novel high bioactivity compound of structure is always a hot spot of chemist and pharmaceutical science worker concern.Due to pyrrole
Coughing up class compound has above-mentioned important biomolecule pharmaceutical value and material science value, therefore its synthetic method is always organic synthesis
One of hot spot of research.
Summary of the invention
The purpose of the present invention is to provide the new synthetic methods of pyrrolo- [3,4-b] quinoline -1,8- derovatives.
To achieve the above object, technical solution of the present invention is specific as follows:
A kind of synthetic method of pyrrolo- [3,4-b] quinoline -1,8- derovatives, comprising: in ethanol solution, returning
Under the conditions of stream, aldehyde, 1- benzyl -2,4- dioxo pyrrolidin -3- carboxylic acid, ethyl ester, ketones with Enamino-esters are reacted, target product is obtained.
Further, the aldehyde, 1- benzyl -2,4- dioxo pyrrolidin -3- carboxylic acid, ethyl ester, ketones with Enamino-esters molar ratio be 1:
1:1。
Further, the aldehyde is mono-substituted virtue or the benzaldehyde with halogen atom and nitro.
Further, the quantity of the substituent group is no more than 3, and the position of substituent group is in the o-, m- and/or right of aldehyde radical
Position.
Further, the synthetic method specifically includes: the aldehyde of 0.04 mM of addition, 0.04 in 95% ethanol solution
MM 1- benzyl -2,4- dioxo pyrrolidin -3- carboxylic acid, ethyl ester and 0.04 mM of ketones with Enamino-esters, back flow reaction 6-8 it is small
When to get arrive corresponding pyrrolo- [3,4-b] quinoline -1,8- derovatives.
Compared with prior art, beneficial effects of the present invention:
Synthetic method of the invention, under the conditions of 95% alcohol reflux, aldehyde, 1- benzyl -2,4- dioxo pyrrolidin -3- carboxylic
Acetoacetic ester has simply and efficiently synthesized pyrrolo- [3,4-b] quinoline derivatives with up to three component one kettle way of ketones with Enamino-esters derived from rice ketone
Object.This method has the advantages such as raw material is easy to get, yield is higher, simple to operation, atom economy utilization rate height, meets greenization
Requirement can be used as the new way of synthesis pyrrolo- [3,4-b] quinolines.
Specific embodiment:
Embodiment 1
1- benzyl -4- (2- bromophenyl) -7,7- dimethyl -9- phenyl -6,7,8,9- tetrahydro-1 H-pyrrolo simultaneously [2,3-b] quinoline
Quinoline -3,5 (2H, 4H)-diketone preparation: 2- bromobenzaldehyde (0.04mmol), 1- benzyl -2,4- dioxo pyrrolidin -3- carboxylic acid second
Ester (0.04mmol), ketones with Enamino-esters (0.04mmol) are added 95% ethyl alcohol 2.5mL, react under counterflow condition in 10mL reaction tube
6-8h, TLC monitoring, after fully reacting, are poured into saturated salt solution, stand filtering, the mixing of crude product dehydrated alcohol and DMF
Solvent recrystallizes to get target product (yield 87%).This product is yellow powder, fusing point: 275-276 DEG C.
Embodiment 2
1- benzyl -4- (4- chlorphenyl) -7,7- dimethyl -9- phenyl -6,7,8,9- tetrahydro-1 H-pyrrolo simultaneously [2,3-b] quinoline
Quinoline -3,5 (2H, 4H)-diketone preparation: 4- chlorobenzaldehyde (0.04mmol), 1- benzyl -2,4- dioxo pyrrolidin -3- carboxylic acid second
Ester (0.04mmol), ketones with Enamino-esters (0.04mmol) are added 95% ethyl alcohol 2.5mL, react under counterflow condition in 10mL reaction tube
6-8h, TLC monitoring, after fully reacting, are poured into saturated salt solution, stand filtering, the mixing of crude product dehydrated alcohol and DMF
Solvent recrystallizes to get target product (yield 85%).This product is yellow powder, fusing point: 241-242 DEG C.
Embodiment 3-6
The reaction process of embodiment 3-6 is similar with condition with Examples 1 and 2, the reaction raw materials of each embodiment, reacts item
Part, yield and fusing point are specifically shown in the following table 1.
The reaction raw materials of 1 embodiment 1-6 of table, reaction condition and yield
As shown in Table 1, method of the invention has many advantages, such as that wide application range of substrates, environmental-friendly, Atom economy is high,
Meet the requirement of Green Chemistry, there is good prospects for commercial application.
The characterize data of compound obtained by each embodiment is as follows:
1- benzyl -4- (2- bromophenyl) -7,7- dimethyl -9- phenyl -6,7,8,9- tetrahydro-1 H-pyrrolo simultaneously [2,3-b] quinoline
Quinoline -3,5 (2H, 4H)-diketone (4a)
Yellow solid；IR(KBr,ν,cm-1):2960,1684,1673,1644,1578,1492,1450,1368,
1271,1243,1194,1168,1153,1022,979,960,838,786,745,701,670,617,577,568,513,
455,446；1H NMR(DMSO-d6,400MHz)δ:7.44-7.57(m,7H,ArH),7.19-7.34(m,4H,ArH),7.07
(t,3H,ArH),5.23(s,1H,CH),4.45(d,1H,HCH),4.21(d,1H,HCH),3.52(s,2H,CH2),2.19(t,
2H,CH2),1.98(d,1H,HCH),1.94(d,1H,HCH),0.90(s,3H,CH3),0.83(s,3H,CH3)；13C NMR
(101MHz,DMSO-d6)δ:193.7,169.9,156.9,141.3,137.8,136.6,134.5,131.5,130.9,
129.5,129.4,128.9,128.9,128.6,128.5,128.1,127.7,126.6,125.0,106.4,86.6,53.0,
52.4,49.5,46.1,42.8,32.5,32.4,30.9,28.8,28.3；HRMS(ESI)m/z:Calcd.for
C32H29BrN2NaO2[M+Na]+:575.1310,found:575.1297.
1- benzyl -4- (4- chlorphenyl) -7,7- dimethyl -9- phenyl -6,7,8,9- tetrahydro-1 H-pyrrolo simultaneously [2,3-b] quinoline
Quinoline -3,5 (2H, 4H)-diketone (4b)
Yellow solid；IR(KBr,ν,cm-1):2955,2899,1686,1624,1571,1490,1417,1359,
1315,1276,1213,1203,1146,1106,1088,1057,974,940,912,898,834,819,754,731,702,
656,644,541,514,419；1H NMR(DMSO-d6,400MHz)δ:7.41-7.45(m,4H,ArH),7.34(t,5H,
ArH),7.25-7.29(m,4H,ArH),7.08(t,1H,ArH),6.21(s,1H,CH),5.86(d,1H,HCH),4.73(d,
1H,HCH),4.43(s,1H,HCH),4.05(d,1H,HCH),2.03(s,2H,CH2),1.82(d,1H,HCH),1.73(d,
1H,HCH),0.87(s,3H,CH3),0.84(s,3H,CH3)；13C NMR(101MHz,DMSO-d6)δ:195.5,169.6,
151.7,149.7,145.3,138.4,137.8,131.0,130.2,130.0,129.0,128.3,127.9,127.6,
112.0,110.1,60.2,50.1,48.1,45.1,34.4,32.4,29.3,26.9,21.2,14.6；HRMS(ESI)m/z:
Calcd.For C32H29ClN2NaO2[M+Na]+:531.1815,found:531.1829.
1- benzyl -4- (4- nitrobenzophenone) -7,7- dimethyl -9- phenyl -6,7,8,9- tetrahydro-1 H-pyrrolo is simultaneously [2,3-b]
Quinoline -3,5 (2H, 4H)-diketone (4c)
Yellow solid；IR(KBr,ν,cm-1):3495,2961,1675,1635,1567,1510,1493,1447,
1396,1370,1344,1272,1241,1170,1106,985,864,834,743,701,607,567,503,454,434,
408；1H NMR(DMSO-d6,400MHz)δ:8.17(d,2H,ArH),7.65(d,2H,ArH),7.56(d,5H,ArH),7.18-
7.29(m,3H,ArH),7.08(d,2H,ArH),4.98(s,1H,CH),4.47(d,1H,HCH),4.23(d,1H,HCH),
3.57(s,2H,CH2),2.24(d,1H,HCH),2.19(d,1H,HCH),2.03(t,2H,CH2),0.91(s,3H,CH3),
0.83(s,3H,CH3)；13C NMR(101MHz,DMSO-d6)δ:195.4,172.3,153.5,150.7,149.3,144.7,
141.1,136.8,136.6,129.9,129.2,128.5,127.6,123.1,122.5,111.7,106.2,101.8,60.8,
56.0,52.2,51.9,44.3,42.7,33.2,27.1；HRMS(ESI)m/z:Calcd.for C32H29N3NaO4[M+Na]+:
542.2056,found:542.2074.
1- benzyl -4- (3,4,5- trimethoxyphenyl) -7,7- dimethyl -9- phenyl -6,7,8,9- tetrahydro-1 H-pyrrolo
And [2,3-b] quinoline 3,5 (2H, 4H)-diketone (4d)
Yellow solid；IR(KBr,ν,cm-1):3031,2954,1673,1635,1593,1567,1506,1496,
1447,1421,1397,1320,1306,1247,1229,1195,1174,1156,1126,1008,976,926,798,772,
761,730,712,696,684,589,563,448,437,425；1H NMR(DMSO-d6,400MHz)δ:7.41-7.56(m,
5H,ArH),7.19-7.29(m,3H,ArH),7.11(d,2H,ArH),6.61(s,2H,ArH),4.82(s,1H,CH),4.54
(d,1H,HCH),4.25(d,1H,HCH),3.76(s,6H,2×OCH3),3.63(s,3H,OCH3),3.54(s,2H,CH2),
2.26(t,2H,CH2),2.08(d,1H,HCH),1.97(d,1H,HCH),0.92(s,6H,2×CH3)；13C NMR(101MHz,
DMSO-d6)δ:195.4,172.5,153.4,152.8,149.2,141.7,141.3,136.5,136.2,129.7,128.7,
127.7,127.3,122.9,122.4,111.7,106.4,101.8,61.0,56.3,52.1,51.6,44.3,43.2,33.2,
27.7,27.3；HRMS(ESI)m/z:Calcd.for C35H36N2NaO5[M+Na]+:587.2522,found:587.2513.
1- benzyl -4- (2,3- dichlorophenyl) -7,7- dimethyl -9- phenyl -6,7,8,9- tetrahydro-1 H-pyrrolo simultaneously [2,3-
B] quinoline -3,5 (2H, 4H)-diketone (4e)
Yellow solid；IR(KBr,ν,cm-1):3061,2956,1682,1637,1566,1495,1448,1419,
1400,1368,1310,1273,1245,1193,1167,1153,1110,1045,980,965,938,923,789,761,
733,707,697,674,565,454,447,428,411；1H NMR(DMSO-d6,400MHz)δ:7.43-7.58(m,7H,
ArH),7.19-7.33(m,4H,ArH),7.06(d,2H,ArH),5.33(s,1H,CH),4.46(d,1H,HCH),4.20(d,
1H,HCH),3.54(s,2H,CH2),2.19(t,2H,CH2),1.98(d,1H,HCH),1.95(d,1H,HCH),0.90(s,3H,
CH3),0.83(s,3H,CH3)；13C NMR(101MHz,DMSO-d6)δ:193.2,170.4,158.0,144.2,138.4,
137.5,132.6,131.9,131.0,129.6,129.3,129.3,128.8,128.7,128.4,128.3,127.7,
105.5,86.0,53.5,51.9,49.6,45.5,42.7,32.7,31.2,29.2,27.8；HRMS(ESI)m/z:
Calcd.for C32H28Cl2N2NaO2[M+Na]+:565.1426,found:565.1428.
1- benzyl -4- (2,6- dichlorophenyl) -7,7- dimethyl -9- phenyl -6,7,8,9- tetrahydro-1 H-pyrrolo simultaneously [2,3-
B] quinoline -3,5 (2H, 4H)-diketone (4f)
Yellow solid；IR(KBr,ν,cm-1):3059,2963,1677,1640,1574,1492,1450,1434,
1402,1369,1313,1298,1271,1242,1197,1164,1151,1107,1080,1023,984,960,844,822,
777,758,721,702,671,617,569,513,454,445,433,410；1H NMR(DMSO-d6,400MHz)δ:7.53-
7.59(m,4H,ArH),7.41(d,1H,ArH),7.19-7.35(m,6H,ArH),7.05(d,2H,ArH),5.78(s,1H,
CH),4.43(d,1H,HCH),4.22(d,1H,HCH),3.49(d,2H,CH2),2.15(d,2H,CH2),1.97(d,1H,
HCH),1.90(d,1H,HCH),0.89(s,3H,CH3),0.87(s,3H,CH3)；13C NMR(101MHz,DMSO-d6)δ:
195.2,169.3,153.7,151.6,138.4,138.1,137.6,137.3,135.3,130.9,130.7,130.3,
130.0,129.7,129.5,129.0,128.6,128.6,127.7,127.6,109.9,106.7,50.1,48.0,44.9,
33.1,32.1,31.2,29.4,27.0；HRMS(ESI)m/z:Calcd.for C32H28Cl2N2NaO2[M+Na]+:565.1426,
found:565.1428.
Claims (5)
1. a kind of synthetic method of pyrrolo- [3,4-b] quinoline -1,8- derovatives.It is characterised by comprising: molten in ethyl alcohol
In liquid, under reflux conditions, aldehyde, 1- benzyl -2,4- dioxo pyrrolidin -3- carboxylic acid, ethyl ester, ketones with Enamino-esters is reacted, mesh is obtained
Mark product.
2. synthetic method according to claim 1, which is characterized in that the aldehyde, 1- benzyl -2,4- dioxo pyrrolidin -
3- carboxylic acid, ethyl ester, ketones with Enamino-esters molar ratio be 1:1:1.
3. synthetic method according to claim 2, which is characterized in that the aldehyde is mono-substituted fragrant or with halogen atom
With the benzaldehyde of nitro.
4. synthetic method according to claim 3, which is characterized in that the quantity of the substituent group is no more than 3, substituent group
Position the o-, m- of aldehyde radical and/or contraposition.
5. synthetic method according to claim 1, which is characterized in that the synthetic method specifically includes: in 95% ethyl alcohol
0.04 mM of aldehyde, 0.04 mM of 1- benzyl -2,4- dioxo pyrrolidin -3- carboxylic acid, ethyl ester and 0.04 are added in solution
MM ketones with Enamino-esters, back flow reaction 6-8 hours is to get arriving corresponding pyrrolo- [3,4-b] quinoline -1,8- derovatives.
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