CN108752281A - A kind of barbiturates-cyclohexene spiro-compound and its synthetic method - Google Patents
A kind of barbiturates-cyclohexene spiro-compound and its synthetic method Download PDFInfo
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Abstract
The invention discloses a kind of barbiturates-cyclohexene spiro-compounds and its synthetic method for carrying imido grpup, belong to technical field of organic chemistry.Using 1,1- dicyanos -1,3- diene 1 and 1, formal [5+1] cyclisation occurs in the presence of a base for 3- dimethyl barbituric acids, barbiturates-spiro-compound 2 of the high selectivity with function dough.The synthetic method is applicable to a variety of different types of 1,1- dicyanos 1, and 3- diolefinic compounds 1 have many advantages, such as that raw material is easy to get, is easy to operate, mild condition, reaction yield are high, can expand quantitative response.The method of the present invention is reacted using cycloaddition mode, and Atom economy is good；Using organocatalysis, the use of transition-metal catalyst is avoided, heavy metal pollution is not present in product.
Description
Technical field
The present invention relates to the preparation methods of a kind of spiro-compound, and in particular to a kind of barbiturates-hexamethylene alkenes spiral shell
Cycle compound and its synthetic method, belong to technical field of organic synthesis.
Background technology
Barbiturates (also known as malonyl urea), entitled 2,4, the 6- pyrimidine trione of chemistry can be used as analytical reagent, organic synthesis
The catalyst etc. of raw material, the intermediate of plastics and dyestuff, polymerisation；Two hydrogen atom quilts on malonyl urea methylene
Part after alkyl substitution is known as barbituric acid derivatives, and being one kind has the active compound of valuable pharmacological, has calmness, fiber crops
Liquor-saturated, antianxiety is anticonvulsion, analgesia, anticancer, the various actives such as anti-AIDS and immunological regulation (Bioorg.Med.Chem.2011,
19,4985；CNSNeurosci.Ther.2009,15,24；CNSDrugs.2008,22,1037；
Clin.CancerRes.2004,10,4038.).Wherein a system is also showed that as the spiral shell barbiturates in barbiturate
The pharmacology and physiological activity (Org.Biomol.Chem.2017,15,5298 of row；TetrahedronLett.2017,58,2865；
Adv.Synth.Catal.2016,358,2619；J.Org.Chem.2015,80,10380；Org.Lett.2016,18,
1302.), and many concerns are caused.
It is some spiral shell barbiturates compounds with physiological activity as shown in Figure 1.For example, compound (I)
(Pharm.Res.1995,12,1240.), (II) and (VII) (Farmaco.2001,56,459.) shows anti-convulsant activity.Spiral shell
Phenobarbital-pentamethylene (III) may be used as modified oligonucleotide structure in conformation lock cell (J.Org.Chem.2002,
67,1302.).Spiral shell barbital-pyrrolidones (IV) is effective inhibitor of MMP-13, can be used for osteoarthritis and rheumatoid
Arthritis (Bioorg.Med.Chem.Lett.2005,15,1101.).Spiral shell barbital-pyrrolidines (V) be loop coil neuropeptide seemingly
Object (J.Org.Chem.2008,73,3608.).Spiral shell barbital-cyclohexanone (VI) is effective alpha-glucosidase restrainer
(Bioorg.Med.Chem.2015,23,6740.), spiral shell barbital-ring butyl oxide link (VIIII) are a kind of TNF converting enzyme inhibitors
(USPat.Appl.2003,0229084.).Other than biologic importance, these loop coils are widely used in synthesizing new and match
Body, catalyst and some special organic optoelectronic synthetic materials.Therefore, exploitation one kind efficiently synthesizing barbiturates loop coil class
The method for closing object is worthy of expecting.
It investigates document to find, often be spread out by the condensation reaction between barbiturates and corresponding carbonyl derivative (aldehyde and ketone)
Cycloaddition between raw barbiturates alkene and acetylenic ketone, 3- isosulfocyanate radicals hydroxyindole or connection olefin(e) acid ester builds barbiturates-
Spirocyclic derivatives, but barbiturates and 1 is directly replaced by N, N '-two, the series connection cyclisation between 1- dicyano -1,3- diene is anti-
Barbital acids-cyclohexene spiro-compound should be built even to be rarely reported.In consideration of it, the synthetic method that is simple and efficient of development and
Various barbital acids spiro-compound is very important.
Invention content
The technical problem to be solved by the present invention is to provide a kind of synthetic method of barbiturates-cyclohexene spiro-compound,
Be provided in particular in it is a kind of under identical solvent directly by the regulation and control of catalyst, two molecule substrates carry out two kinds of Cyclization not
With barbiturates-cyclohexene spiro-compound of function dough.
The method of the present invention is a kind of 1,1- dicyano -1,3- diene and 1,3- dimethyl barbituric acids of effective amine catalysis
The method of reaction synthesis barbiturates-cyclohexene spiro-compound.This method is to be catalyzed to carry out by amine.The equation of reaction is used
Following formula indicates：
It is characterised in that it includes following operation：By 1,1- dicyanos -1,3- diene 1 and 1,3- dimethyl barbituric acids,
In organic solvent, using base catalyzed reactions, barbiturates-cyclohexene spiro-compound 2 with imido grpup is obtained.
Wherein, R1For alkyl, phenyl or substituted-phenyl, R2For phenyl, substituted-phenyl, thienyl or naphthalene.
Further, the R1Middle alkyl is selected from isopropyl, cyclohexyl or cyclopropyl, R1Substituent group is selected from substituted-phenyl
It is one or more in methyl, methoxyl group or chlorine；R2Substituent group is in fluorine, chlorine, bromine, nitro, methyl, methoxyl group in substituted-phenyl
It is one or more.
Further, in the base catalyzed reactions, alkali includes organic base or inorganic base.Organic base is selected from diisopropylamine, three
Ethamine, diisopropyl ethyl amine, DBU, tetramethylguanidine, methenamine, triethylene diamine, tetramethylethylenediamine, three tertiary amines, diethyl
Base amine, piperidines, tert-butylamine, n-butylamine, nafoxidine, 4-dimethylaminopyridine, pyridine, N, N '-dimethyl-ethylenediamines, N, N- bis-
The bis- dimethylamino naphthalenes of methyl ethylenediamine, 1,8-；Inorganic base is selected from potassium carbonate, cesium carbonate or sodium hydroxide.Alkali preferably is selected from：Three second
Amine, diisopropyl ethyl amine, tetramethylguanidine, DBU, diisopropylamine.
Further, the reaction dissolvent can be polarity or nonpolar solvent, such as dichloromethane, chloroform, dichloro
Ethane, methanol, acetonitrile, tetrahydrofuran, toluene, dimethylformamide, ethyl acetate, ether.It is preferred that tetrahydrofuran.
Further, 1,1- dicyanos -1,3- diene 1,1,3- dimethyl barbituric acids and base catalyst molar ratio
It is 1:1-1.5：0.01-0.1.Specific ratio is selected according to the selection of catalyst, such as selection i-Pr2NH is catalyst
When, three's molar ratio is preferably 1:1.2:0.05；As selection Et3When N is catalyst, three's molar ratio is preferably 1:1.2:
0.02。
It is detached by column chromatography method using the method for the present invention products therefrom.Eluant, eluent used is for polar solvent
With the mixed solvent of nonpolar solvent.Recommendation solvent is ethyl acetate-petroleum ether mixed solvent, and volume ratio is polar solvent：
Nonpolar solvent=1：10.Ethyl acetate：Petroleum ether=1：10.
Further, this reaction preferably carries out at room temperature.With i-Pr2NH (5mol%) or Et3N (2mol%) is catalyzed
For agent, reaction yield is good, obtains target compound 2 respectively with 45-99% and 46-97%.
Invention advantageous effect：
1) building-up process is simple, efficient, and by 1,1- dicyanos -1,3- diene and 1,3- dimethyl barbituric acids are formal
[5+1] cyclization, a step obtain barbiturates-cyclohexene spiro-compound；
2) raw material is cheap and easy to get；Reaction condition is mild, easy to operate；Substrate applied widely and can the amount of being enlarged
Experiment.
Description of the drawings：
Fig. 1 is some spiral shell barbiturates compound structure figures with physiological activity in background technology.
Specific implementation mode
The above of the present invention is described in further details by the following examples, but this should not be interpreted as to this
The range for inventing above-mentioned theme is only limitted to embodiment below, and all technologies realized based on the above of the present invention belong to this hair
Bright range.
Embodiment 1
Reaction condition screens
[5+1] cyclization builds two kinds of differences in form for 1,1- dicyano 1,3- diene and 1,3- dimethyl barbituric acids
The spiral shell barbituric acid compound reaction condition of structure screens：By taking the reaction of substrate 1a and 1,3- dimethyl barbituric acid as an example：
Reaction equation is as follows：
Embodiment 2
The synthesis of barbiturates with imido grpup-cyclohexene spiro-compound 2
At ambient temperature, 1 (0.3mmol), 1,3- dimethyl barbituric acids are sequentially added into reaction bulb
Catalyst i-Pr is added in (0.36mmol), tetrahydrofuran (0.6mL) later2NH (5mol%) or Et3N (2mol%).Reaction knot
Shu Hou, direct silica gel post separation (petrol ether/ethyl acetate=10/1) of crossing obtain corresponding target product 2.Specific experiment data
It is as follows：
3H), 7.31 (s, 3H), 7.13 (s, 2H), 4.17 (d, J=12.1Hz, 1H)；3.91-3.80(m,1H),3.15(s,3H),
3.15 (s, 3H), 3.01 (d, J=19.1Hz, 1H)；13C NMR(75MHz,CDCl3):δ=169.1,167.3,166.6,
165.6,150.1,137.4,135.8,131.4,129.3,129.2,129.1,127.7,127.5,114.3,109.6,62.6,
47.3,34.7,28.8,28.4；DEPT-135C NMR(75MHz,CDCl3):δ=131.3,129.2,129.1,129.0,
127.6,127.5,47.3,34.6,28.8,28.4；HRMS(ESI):m/zcalcd for C24H21N4O3 +[M+H]+
413.1608,found:413.1608.
2H), 7.01-6.98 (m, 2H), 4.13 (d, J=12.7Hz, 1H), 3.88-3.78 (m, 1H), 3.18 (s, 3H), 3.16 (s,
3H), 2.98 (d, J=18.6Hz, 1H), 2.31 (s, 3H)；13C NMR(75MHz,CDCl3):δ=169.2,167.5,166.7,
165.8,150.2,139.2,137.5,132.7,131.4,129.9,129.1,127.6,114.4,109.6,62.6,47.0,
34.9,28.9,28.5,21.3；HRMS(ESI)m/z calcd forC25H23N4O3 +[M+H]+427.1765,found:
427.1762.
(m, 3H), 7.05-7.02 (m, 2H), 6.81-6.78 (m, 2H), 4.13 (dd, J=12.3Hz, J=4.2Hz, 1H)；3.86-
3.76(m,1H),3.77(s,3H),3.18(s,3H),3.16(s,3H),3.01-2.93(m,1H)；13C NMR(75MHz,
CDCl3):δ=169.2,167.4,166.7,165.7,160.0,150.2,137.4,131.3,129.1,12 8.8,127.6,
127.5,114.4,109.5,62.7,55.3,46.6,35.0,28.9,28.4；HRMS(ESI)m/z calcd for
C25H23N4O4 +[M+H]+443.1714,found:443.1712.
J=12.2Hz, 1H)；3.85 (dd, J=18.9Hz, J=12.5Hz 1H), 3.19 (s, 3H), 3.17 (s, 3H), 2.99 (d, J
=19.0Hz, 1H)；13C NMR(75MHz,CDCl3):δ=168.9,167.2,166.4,165.4,150.1,137.3,
131.9,131.5,129.7,129.6,129.1,127.5,116.4,116.1,114.3,109.4,62.4,46.1,35.0,
28.9,28.5；HRMS(ESI)m/z calcd for C24H20FN4O3 +[M+H]+431.1514,found:431.1510.
7.11-7.06 (m, 2H), 4.21 (d, J=12.1Hz, 1H)；3.87 (dd, J=18.8Hz, J=12.5Hz 1H), 3.21 (s,
3H), 3.19 (s, 3H), 2.99 (d, J=19.2Hz, 1H)；13C NMR(75MHz,CDCl3):δ=168.8,167.2,166.3,
165.4,150.1,137.3,135.2,134.6,131.5,129.5,129.3,129.2,127.5,114.3,109.3,62.3,
46.1,34.9,29.0,28.6；HRMS(ESI)m/z calcd for C24H20ClN4O3 +[M+H]+447.1218,found:
447.1214.
7.03-7.01 (m, 1H), 4.17 (dd, J=12.2Hz, J=4.2Hz, 1H)；3.83 (dd, J=19.0Hz, J=12.3Hz
1H), 3.19 (s, 3H), 3.17 (s, 3H), 3.00 (dd, J=19.0Hz, J=4.4Hz, 1H)；13C NMR(75MHz,CDCl3):
δ=168.7,167.1,166.2,165.1,150.0,138.0,137.2,135.2,131.4,13 0.3,129.4,129.1,
127.9,127.5,126.1,114.2,109.4,62.2,46.5,34.5,28.9,28.4；HRMS(ESI)m/z calcd for
C24H20ClN4O3 +[M+H]+447.1218,found:447.1214.
7.22-7.13 (m, 3H), 4.84 (dd, J=12.2Hz, J=4.3Hz, 1H)；3.70 (dd, J=18.8Hz, J=12.2Hz
1H), 3.23 (s, 3H), 3.19 (s, 3H), 2.98 (dd, J=18.9Hz, J=4.4Hz, 1H)；13C NMR(75MHz,CDCl3):
δ=167.9,167.9,166.8,164.9,150.3,137.2,134.6,134.2,131.5,13 0.8,130.2,129.1,
127.7,127.6,127.4,114.3,109.6,61.4,42.5,35.5,29.2,28.7；HRMS(ESI)m/z calcd for
C24H20ClN4O3 +[M+H]+447.1218,found:447.1213.
10H), 5.07 (dd, J=12.1Hz, J=3.7Hz, 1H)；3.93 (dd, J=18.8Hz, J=12.2Hz, 1H), 3.16 (s,
3H), 3.06 (dd, J=18.7Hz, J=3.9Hz, 1H), 2.61 (s, 3H)；13C NMR(75MHz,CDCl3):δ=168.8,
168.0,167.1,165.4,149.9,137.3,134.0,132.2,131.0,130.0,129.2,129.1,127.6,
127.0,126.5,124.7,124.5,122.8,114.5,110.0,62.5,41.0,35.9,28.5,28.4；HRMS(ESI)
m/z calcd for C28H23N4O3 +[M+H]+463.1765,found:463.1760.
(dd, J=12.0Hz, J=4.4Hz, 1H)；3.84 (dd, J=19.1Hz, J=12.2Hz, 1H), 3.27 (s, 3H), 3.19 (s,
3H),3.19-3.10(m,1H)；13C NMR(75MHz,CDCl3):δ=168.9,167.0,166.0,165.1,150.3,
138.6,137.1,131.4,129.1,127.5,127.3,126.8,126.1,114.2,109.3,62.6,42.1,36.6,
29.1,28.7；HRMS(ESI)m/z calcd for C22H19N4O3S+[M+H]+419.1172,found:419.1170.
MHz,CDCl3):δ=169.2,167.4,166.8,165.5,150.1,142.2,135.9,134.5,129.8,12 9.3,
129.2,127.7,127.6,114.7,108.9,62.6,47.4,34.5,28.8,28.4,21.6；HRMS(ESI)m/zcalcd
for C25H23N4O3 +[M+H]+427.1765,found:427.1761.
(m, 1H), 3.16 (s, 3H), 3.14 (s, 3H), 3.01 (dd, J=18.1Hz, J=4.2Hz, 1H)；13C NMR(75MHz,
CDCl3):δ=169.2,167.5,166.9,164.7,162.4,150.2,136.0,129.9,129.4,12 9.3,129.2,
127.7,115.0,114.5,107.9,62.7,55.6,47.3,34.3,28.8,28.4；HRMS(ESI)m/z calcd for
C25H23N4O4 +[M+H]+443.1714,found:443.1715.
1H),3.15(s,3H),3.14(s,3H),3.00-2.93(m,1H)；13C NMR(75MHz,CDCl3):δ=169.0,167.3,
166.3,164.0,150.0,137.7,135.7,135.6,129.5,129.4,129.2,129.0,127.7,114.1,
109.9,62.5,47.3,34.6,28.9,28.4；HRMS(ESI)m/z calcd for C24H20ClN4O3 +[M+H]+
447.1218,found:447.1214.
(m, 2H), 3.13 (s, 3H), 3.12 (s, 3H), 2.71 (dd, J=19.2Hz, J=4.3Hz, 1H), 1.25 (t, J=7.1Hz,
6H)；13C NMR(75MHz,CDCl3):δ=175.5,169.0,167.2,166.4,150.0,136.0,129.2,129.1,
127.6,113.3,107.0,62.8,47.2,36.4,28.7,28.3,28.2,20.8,19.7；HRMS(ESI)m/z calcd
for C21H23N4O3 +[M+H]+379.1765,found:379.1764.
Hz, J=12.3Hz, 1H), 3.05 (s, 3H), 3.04 (s, 3H), 2.92-2.84 (m, 1H), 2.67 (dd, J=19.1Hz, J=
4.4Hz,1H),1.81-1.65(m,5H),1.46-1.35(m,6H)；13C NMR(75MHz,CDCl3):δ=175.0,169.1,
167.2,166.5,150.1,136.1,129.2,129.1,127.7,113.5,109.1,62.8,47.2,30.9,29.8,
29.7,28.8,28.3,27.0,25.8,25.6；HRMS(ESI)m/z calcd for C24H27N4O3 +[M+H]+419.2078,
found:419.2076.
Embodiment above describes the basic principles and main features and advantage of the present invention.The technical staff of the industry should
Understand, the present invention is not limited to the above embodiments, and the above embodiments and description only describe the originals of the present invention
Reason, under the range for not departing from the principle of the invention, various changes and improvements may be made to the invention, these changes and improvements are each fallen within
In the scope of protection of the invention.
Claims (10)
1. one kind carries barbiturates-cyclohexene spiro-compound of imido grpup, structural formula is as follows：
Wherein, R1For alkyl, phenyl or substituted-phenyl, R2For phenyl, substituted-phenyl, thienyl or naphthalene.
2. a kind of synthetic method of barbiturates-cyclohexene spiro-compound with imido grpup as described in claim 1, special
Sign is, including operates as follows：By 1,1- dicyanos -1,3- diene 1 and 1,3- dimethyl barbituric acids, in organic solvent,
Using base catalyzed reactions, imido grpup barbiturates-cyclohexene spiro-compound 2 is obtained, reaction equation is：
Wherein, R1For alkyl, phenyl or substituted-phenyl, R2For phenyl, substituted-phenyl, thienyl or naphthalene.
3. carrying the synthetic method of barbiturates-cyclohexene spiro-compound of imido grpup, feature according to claim 2
It is：The R1Middle alkyl is selected from isopropyl, cyclohexyl or cyclopropyl, R1In substituted-phenyl substituent group be selected from methyl, methoxyl group or
It is one or more in chlorine；R2Substituent group is one or more in fluorine, chlorine, bromine, nitro, methyl, methoxyl group in substituted-phenyl.
4. carrying the synthetic method of barbiturates-cyclohexene spiro-compound of imido grpup, feature according to claim 2
It is：The reaction dissolvent is selected from dichloromethane, chloroform, dichloroethanes, methanol, acetonitrile, tetrahydrofuran, toluene, diformazan
Base formamide, ethyl acetate, ether.
5. carrying the synthetic method of barbiturates-cyclohexene spiro-compound of imido grpup, feature according to claim 2
It is：In the base catalyzed reactions, alkali includes organic base or inorganic base.
6. according to the conjunction for the barbiturates-cyclohexene spiro-compound for carrying imido grpup described in claim 2,4 or 5 any one
At method, it is characterised in that：The alkali is selected from diisopropylamine, triethylamine, diisopropyl ethyl amine, DBU, tetramethylguanidine, Wu Luo
Tropine, triethylene diamine, tetramethylethylenediamine, three tertiary amines, diethylamide, piperidines, tert-butylamine, n-butylamine, nafoxidine, 4- bis-
Methylamino pyridine, pyridine, N, N '-dimethyl-ethylenediamines, N, the bis- dimethylamino naphthalenes of N- dimethyl-ethylenediamines, 1,8-, potassium carbonate, carbon
Sour caesium or sodium hydroxide.
7. carrying the synthetic method of barbiturates-cyclohexene spiro-compound of imido grpup, feature according to claim 6
It is：The alkali is selected from triethylamine, diisopropyl ethyl amine, tetramethylguanidine, DBU, diisopropylamine.
8. carrying the synthetic method of barbiturates-cyclohexene spiro-compound of imido grpup, feature according to claim 2
It is：1,1- dicyanos -1,3- the diene 1,1,3- dimethyl barbituric acids and organic alkali catalyst molar ratio are 1:1-
1.5:0.01-0.1。
9. carrying the synthetic method of barbiturates-cyclohexene spiro-compound of imido grpup, feature according to claim 2
It is：Products therefrom is after column chromatography, isolated sterling.
10. the synthetic method of barbiturates-cyclohexene spiro-compound of imido grpup is carried according to claim 2, it is special
Sign is：Reaction carries out at room temperature.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114430068A (en) * | 2020-10-29 | 2022-05-03 | 深圳市研一新材料有限责任公司 | Lithium ion battery electrolyte |
| CN114430068B (en) * | 2020-10-29 | 2024-01-23 | 深圳市研一新材料有限责任公司 | Lithium ion battery electrolyte |
| CN113880704A (en) * | 2021-10-18 | 2022-01-04 | 西北师范大学 | Rapid synthesis18Method for marking aldehyde compound by O |
| CN113880704B (en) * | 2021-10-18 | 2023-07-21 | 西北师范大学 | Quick synthesis 18 Method for marking aldehyde compound by O |
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