CN113045576B - Construction method of pyrimido [1,2-b ] indazole parent nucleus - Google Patents

Construction method of pyrimido [1,2-b ] indazole parent nucleus Download PDF

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CN113045576B
CN113045576B CN202110305406.0A CN202110305406A CN113045576B CN 113045576 B CN113045576 B CN 113045576B CN 202110305406 A CN202110305406 A CN 202110305406A CN 113045576 B CN113045576 B CN 113045576B
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刘想
曹华
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Guangdong Pharmaceutical University
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Abstract

The invention relates to a construction method of a pyrimido [1,2-b ] indazole parent nucleus and a pyrimido [1,2-b ] indazole compound prepared by the method.

Description

Construction method of pyrimido [1,2-b ] indazole parent nucleus
Technical Field
The invention relates to the field of organic chemistry, in particular to a method for constructing a pyrimido [1,2-b ] indazole parent nucleus.
Background
Pyrimido [1,2-b ] s]Indazole (pyrimido [1,2-b ]]indole) parent nucleus having a structure represented by the following formula
Figure BDA0002986663790000011
The parent nucleus is present in a variety of biologically active small molecules.
Chinese patent application CN103370321A discloses a substituted pyrimido [1,2-b ] indazole compound having the structure of the following formula
Figure BDA0002986663790000012
The compounds have a modulating effect on the PI3K/AKT pathway, wherein pyrimido [1,2-b ] is]An indazole core is constructed by the following method,
Figure BDA0002986663790000013
jismy et al (b.jismy, a.el Qami, a.
Figure BDA0002986663790000015
R.Frlan,J.Kos,S.Gobec,D.Knez,M.Abarbri,Pyrimido[1,2-b]indole derivatives of human monoamine oxidase with polyamine inhibitory activity pyrido [1,2-b ] is reported]Indazole derivatives having the structure
Figure BDA0002986663790000014
The mother core construction method is similar to that in CN 103370321A.
Lei Li et al (Tetrahedron, 2017(73), 36, 5358-5365) report a process for the preparation of pyrimido [1,2-b ] indazole derivatives, as follows,
Figure BDA0002986663790000021
sandip Gangadhar Balwe et al (org. Biomol. chem.,2018,16,1287-1296) reported a process for the preparation of pyrimido [1,2-b ] indazole derivatives as follows,
Figure BDA0002986663790000022
the organic selenium compound has important significance in organic catalysis, material science and medical industry (ACS Catal.2017,7, 5828-. In particular, they have good biological activities such as antidepressant, anticancer, antitumor and anti-inflammatory activities, etc. (eur.j.med.chem.,2014,87, 306; j.m.chem.,2015,90, 184;). N-fused heterocycles, selenoamidones, are widely found in natural products and bioactive molecules and have received a great deal of attention in drug development. The synthesis of several selenoylazacyclic compounds has been reported (Blackwell Science, Oxford, 2000; org. chem. Front.,2019,6, 1906-one 1928.). However, due to the fact that the synthesis difficulty of the N-fused heterocycle is large, and the introduction of elements such as selenium and tellurium into the compound is few, a method for simultaneously introducing a selenium group and a pyrimido [1,2-b ] indazole skeleton into an organic compound is not reported, and the development of a new method for constructing the selenium-substituted pyrimido [1,2-b ] indazole compound becomes a very challenging task.
Disclosure of Invention
The invention aims to provide a construction method of a pyrimido [1,2-b ] indazole parent nucleus, in particular to a synthesis method for introducing selenium and tellurium elements into the 3-position of the pyrimido [1,2-b ] indazole parent nucleus.
The object of the present invention is achieved by the following single scheme.
A method for constructing a pyrimido [1,2-b ] indazole parent nucleus is shown in the following reaction formula
Figure BDA0002986663790000023
The reaction is carried out by the compound 1, the compound 2 and the compound 3 under the condition of the existence of a photosensitizer, photons and Lewis acid.
Further, X is selected from selenium or tellurium.
Further, the photosensitizer is selected from at least one of rose bengal, yellow Y and rhodamine B.
Further, the Lewis acid is selected from FeCl3、AlCl3At least one of AcOH and TFA.
Further, the photons are generated by light between 450nm and 465 nm.
Further, the intensity of the light is 20-50W.
Further, the reaction is carried out in an aprotic solvent.
The solvent may be conventionally selected depending on the solubility of the raw material.
Further, the solvent is selected from at least one of acetonitrile, dichloromethane or toluene.
Further, said R1、R2And R3Each independently selected from H, halogen, alkyl or aryl.
Further, the alkyl group is selected from C1-C6An alkyl group.
Further, the alkyl group is selected from a linear alkyl group, a branched alkyl group, or a cyclic alkyl group, a spiro ring group, or a bridged ring group.
Further, the halogen is selected from fluorine, chlorine, bromine or iodine.
Further, the aryl group is benzene.
Further, the alkyl group and the aryl group may be substituted with at least one substituent selected from the group consisting ofHalogen, C1-C6Alkyl or aryl.
Further, said R1Selected from hydrogen or halogen;
R2is selected from C1-C6Alkyl radical, C1-C6Alkyl substituted C1-C6Alkyl, phenyl or C1-C6Alkyl-substituted phenyl;
R3is selected from C1-C6Alkyl radical, C1-C6Alkyl substituted C1-C6Alkyl, phenyl or C1-C6Alkyl-substituted phenyl;
further, 1eq of compound 1, 0.5 to 1.5eq of compound 2, 0.5 to 1.5eq of compound 3, 0.02 to 0.05eq of photosensitizer, and 0.5 to 2eq of lewis acid were measured by molar equivalents, and the amount of solvent was added so that the concentration of compound 1 was 0.05 to 0.5 mol/L.
The reaction may be carried out by a condensation reaction of aminoindazole and alkynal with a Lewis acid to form intermediate A. On the other hand, diphenyl diselenide is converted to radical cations under the action of a photosensitizer and visible light diffraction. And then capturing diphenyl diselenide free radical positive ions by the intermediate A, and carrying out electrophilic cyclization reaction to generate a target product.
Figure BDA0002986663790000041
The invention also provides a compound obtained by the preparation method of the invention, which has the following structure
Figure BDA0002986663790000042
Wherein R is1、R2And R3As defined above.
The invention has the advantages that:
1. in the preparation method, the substrate has wide application range and high atom economy, and accords with the green chemical concept.
2. The method directly constructs the pyrimido [1,2-b ] indazole parent nucleus in one step, and simultaneously introduces selenium or tellurium element, so that the method is novel and ingenious.
3. The method does not need strong alkali, strong acid, strong oxidizing property or strong corrosive reagent, and is safe and simple to operate.
Drawings
FIG. 1 ultraviolet absorption spectrum of the compound obtained in example 1;
FIG. 2 fluorescence emission spectrum of the compound obtained in example 1.
Detailed Description
The materials used in the present invention are commercially available unless otherwise specified.
Wherein
Rose Bengal (RB): CAS No.: 632-69-9
And (3) rhodamine B: CAS No.: 81-88-9
Deploying red Y: CAS No.: 17372-87-1
Example 1:
39.9mg (0.3mmol) of the 3-aminoindazole, 39.0mg (0.3mmol) of alkynal and 93.6mg (0.3mmol) of diphenyldiselenide shown below were added to a reaction tube with a stirrer, followed by 48.6mg (0.3mmol) of additive FeCl3And 9.1mg (0.009mmol) of the photosensitizer RB, followed by addition of a MeCN (2ml) solvent for dissolution, stirring at room temperature for 12 hours under a 20W LED lamp, spin-drying, and then separating by silica gel chromatography to give the desired product in 80% yield.
Figure BDA0002986663790000051
1H NMR(400MHz,CDCl3)δppm 8.53(s,1H),8.27(d,J＝8.3Hz,1H),7.79(d,J＝8.7Hz,1H),7.65–7.57(m,6H),7.45–7.41(m,2H),7.33–7.27(m,4H).
13C NMR(100MHz,CDCl3)δppm 151.22,148.89,145.48,143.37,134.05,131.35,130.89,129.90,129.67,129.47,128.96,128.64,127.97,121.40,120.58,117.03,116.91,113.82.
HRMS MALDI(m/z):calcd for C22H15N3Se[M+H]+:402.0509,found:402.0511.
Example 2:
45.3mg (0.3mmol) of the 3-aminoindazole shown below, 39.0mg (0.3mmol) of alkynal and 93.6mg (0.3mmol) of diphenyldiselenide are introduced into a reaction tube with stirrer, followed by 48.6mg (0.3mmol) of the additive FeCl3And 9.1mg (0.009mmol) of the photosensitizer RB, followed by addition of a MeCN (2ml) solvent for dissolution, stirring at room temperature for 12 hours under a 20W LED lamp, spin-drying, and then separating by silica gel chromatography to give the desired product in 72% yield.
Figure BDA0002986663790000052
1H NMR(400MHz,CDCl3)δppm 8.55(s,1H),7.64(q,J＝3.5Hz,5H),7.54(s,1H),7.51–7.45(m,3H),7.36–7.27(m,3H),6.91(dd,J＝10.2,7.4Hz,1H).
13C NMR(100MHz,CDCl3)δppm 156.96(d,J＝256.8Hz),152.78(d,J＝4.7Hz),149.63,144.99,141.60,134.57,131.07,131.03,130.19,130.11,130.00,129.59,129.04,128.96,128.80,118.05,112.85(d,J＝4.6Hz),105.12(d,J＝17.7Hz).
HRMS MALDI(m/z):calcd for C22H14FN3Se[M+H]+:420.0415,found:420.0419.
Example 3:
39.3mg (0.3mmol) of the 3-aminoindazole, 43.2mg (0.3mmol) of alkynal and 93.6mg (0.3mmol) of diphenyldiselenide shown below were added to a reaction tube with a stirrer, followed by 48.6mg (0.3mmol) of the additive FeCl3And 9.1mg (0.009mmol) of the photosensitizer RB, followed by addition of a MeCN (2ml) solvent for dissolution, stirring at room temperature for 12 hours under a 20W LED lamp, spin-drying, and then separating by silica gel chromatography to give the desired product in 76% yield.
Figure BDA0002986663790000061
1H NMR(400MHz,CDCl3)δppm 8.50(s,1H),8.26(dd,J＝8.3,1.1Hz,1H),7.81(d,J＝8.6Hz,1H),7.57(dd,J＝8.1,6.4Hz,3H),7.47–7.41(m,4H),7.35–7.27(m,4H),2.49(s,3H).
13C NMR(100MHz,CDCl3)δppm 151.17,148.82,145.59,143.31,141.22,134.08,134.03,129.89,129.82,129.69,129.58,128.62,128.39,121.31,120.57,116.96,116.93,113.82,21.89.
HRMS MALDI(m/z):calcd for C23H17N3Se[M+H]+:416.0666,found:416.0661.
Example 4:
39.3mg (0.3mmol) of the 3-aminoindazole, 41.4mg (0.3mmol) of alkynal and 93.6mg (0.3mmol) of diphenyldiselenide shown below were added to a reaction tube with a stirrer, followed by 48.6mg (0.3mmol) of additive FeCl3And 9.1mg (0.009mmol) of the photosensitizer RB, followed by addition of a MeCN (2ml) solvent for dissolution, stirring at room temperature for 12 hours under a 20W LED lamp, spin-drying, and then separating by silica gel chromatography to give the desired product in 65% yield.
Figure BDA0002986663790000062
1H NMR(400MHz,CDCl3)δppm 8.63(s,1H),8.27(d,J＝8.3Hz,1H),7.88(d,J＝8.7Hz,1H),7.63(ddd,J＝8.3,6.8,1.1Hz,1H),7.43–7.38(m,2H),7.29–7.25(m,4H),3.67(t,2H),1.85–1.79(m,2H),1.49–1.42(m,2H),1.40–1.34(m,2H),0.90(t,J＝7.2Hz,3H).
13C NMR(100MHz,CDCl3)δppm 151.49,151.29,150.33,143.28,132.04,130.65,130.11,129.84,127.93,121.17,120.87,116.59,114.51,113.88,32.03,31.78,26.07,22.54,14.07.
HRMS MALDI(m/z):calcd for C21H21N3Se[M+H]+:396.0979,found:396.0981.
Example 5:
39.3mg (0.3mmol) of the 3-aminoindazole, 41.4mg (0.3mmol) of alkynal and 110.7mg (0.3mmol) of diphenyldiselenide shown below were added to a reaction tube with a stirrer, followed by 48.6mg (0.3mmol) of additive FeCl3And 9.1mg (0.009mmol) of the photosensitizer RB, followed by addition of a MeCN (2ml) solvent for dissolution, stirring at room temperature for 12 hours under a 20W LED lamp, spin-drying, and then separating by silica gel chromatography to obtain the desired product in 60% yield.
Figure BDA0002986663790000071
1H NMR(400MHz,CDCl3)δppm 9.94(s,1H),8.74(s,1H),8.33(d,J＝8.3Hz,1H),7.83(d,J＝8.7Hz,1H),7.72(d,J＝8.1Hz,2H),7.67–7.56(m,6H),7.41(d,J＝8.2Hz,2H),7.37–7.31(m,1H).
13C NMR(100MHz,CDCl3)δppm 191.33,151.65,150.16,148.03,140.06,137.69,135.33,131.40,131.03,130.56,130.37,130.06,129.62,128.89,121.87,120.75,117.09,114.03.
HRMS MALDI(m/z):calcd for C23H15N3OSe[M+H]+:430.0459,found:430.0467.
Example 6:
39.3mg (0.3mmol) of the 3-aminoindazole, 41.4mg (0.3mmol) of alkynal and 65.3mg (0.3mmol) of dimethyldiselenide shown below were added to a reaction tube with a stirrer, followed by 48.6mg (0.3mmol) of the additive FeCl3And 9.1mg (0.009mmol) of the photosensitizer RB, followed by addition of a MeCN (2ml) solvent for dissolution, stirring at room temperature for 12 hours under a 20W LED lamp, spin-drying, and then separating by silica gel chromatography to give the desired product in 71% yield.
Figure BDA0002986663790000072
1H NMR(400MHz,CDCl3)δppm 8.81(s,1H),8.32(d,J＝8.3Hz,1H),7.80(d,J＝8.7Hz,1H),7.68–7.58(m,6H),7.34–7.30(m,1H),2.85(q,J＝7.4Hz,2H),1.35(t,J＝7.4Hz,3H)..
13C NMR(100MHz,CDCl3)δppm 151.17,148.98,146.37,143.55,131.65,130.75,129.87,129.82,128.89,121.34,120.61,116.94,114.86,113.83,22.77,15.34.
HRMS MALDI(m/z):calcd for C18H15N3Se[M+H]+:354.0509,found:354.0508.
Example 7:
39.3mg (0.3mmol) of the 3-aminoindazole, 41.4mg (0.3mmol) of alkynal and 123.9mg (0.3mmol) of diphenylditelluril shown below were charged to a reaction tube with a stirrer, followed by 48.6mg (0.3mmol) of additive FeCl3And 9.1mg (0.009mmol) of the photosensitizer RB, followed by addition of a MeCN (2ml) solvent for dissolution, stirring at room temperature for 12 hours under a 20W LED lamp, spin-drying, and then separating by silica gel chromatography to give the desired product in 68% yield.
Figure BDA0002986663790000073
1H NMR(400MHz,CDCl3)δppm 8.43(s,1H),8.25(d,J＝8.3,1.1Hz,1H),7.85–7.78(m,3H),7.64(s,5H),7.59–7.55(m,1H),7.41(td,J＝7.6,7.1,1.4Hz,1H),7.33–7.27(m,3H).
13C NMR(100MHz,CDCl3)δppm 150.84,150.48,143.56,140.31,133.88,131.08,130.23,129.90,129.49,129.37,129.08,121.23,120.58,116.83,113.67,113.44,102.76.
HRMS MALDI(m/z):calcd for C22H15N3Te[M+H]+:452.0406,found:452.0406.
Effect example 1 fluorescence Performance test of the Compound produced according to the present invention
The compound of example 1 was dissolved in various solvents to prepare 5X 10-6Mu.g/ml of the solution was subjected to UV absorption spectroscopy to obtain FIG. 1. Fluorescence emission spectroscopy tests were performed on the solutions of example 1 dissolved in different solvents using the maximum absorption wavelength in the corresponding solution as excitation light, resulting in fig. 2.
As can be seen, pyrimido [1,2-b ] obtained in example 1]Indazoles exhibit good optical properties. The compound is prepared into 5 × 10-6μ g/ml, 270-320nm in DCM, DCE, MeCN, MeOHStrong absorption, two strong emission peaks at 340-360nm and 425-440 nm. The strong fluorescence emission makes the fluorescent material a reliable candidate material of the luminescent material, and the fluorescent molecules with double emission peaks have certain application potential in the anti-counterfeiting material.
Finally, it should be noted that the above-mentioned contents are only used for illustrating the technical solutions of the present invention, and not for limiting the protection scope of the present invention, and that the simple modifications or equivalent substitutions of the technical solutions of the present invention by those of ordinary skill in the art can be made without departing from the spirit and scope of the technical solutions of the present invention.

Claims (5)

1. A method for constructing a pyrimido [1,2-b ] indazole parent nucleus is shown in the following reaction formula
Figure FDA0003473249700000011
The X is selected from Se or Te;
the R is1Selected from hydrogen or halogen;
R2is selected from C1-C6Alkyl radical, C1-C6Alkyl substituted C1-C6Alkyl, phenyl or C1-C6Alkyl-substituted phenyl;
R3is selected from C1-C6Alkyl radical, C1-C6Alkyl substituted C1-C6Alkyl, phenyl or C1-C6Alkyl-substituted phenyl;
1eq of compound 1, 0.5-1.5eq of compound 2, 0.5-1.5eq of compound 3, 0.02-0.05eq of photosensitizer, 0.5-2eq of lewis acid by molar equivalent, and adding an amount of solvent so that the concentration of compound 1 is 0.05-0.5 mol/L; the photosensitizer is selected from at least one of rose bengal, yellow pink Y and rhodamine B; the Lewis acid is selected from FeCl3、AlCl3At least one of AcOH and TFA; the photons are generated by light between 450nm and 465 nm.
2. The method of claim 1, wherein the light intensity of the reaction is 20-50W.
3. The process according to claim 1, characterized in that the reaction is carried out in an aprotic solvent.
4. The method of claim 1, wherein the solvent is at least one of acetonitrile, dichloromethane, or toluene.
5. A pyrimido [1,2-b ] indazole derivative having the structure of formula
Figure FDA0003473249700000012
The X is selected from Se or Te;
the R is1Selected from hydrogen or halogen;
R2is selected from C1-C6Alkyl radical, C1-C6Alkyl substituted C1-C6Alkyl, phenyl or C1-C6Alkyl-substituted phenyl;
R3is selected from C1-C6Alkyl radical, C1-C6Alkyl substituted C1-C6Alkyl, phenyl or C1-C6Alkyl-substituted phenyl;
wherein the pyrimido [1,2-b ] indazole derivative is obtained by the method for constructing a pyrimido [1,2-b ] indazole core according to claim 1.
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Publication number Priority date Publication date Assignee Title
CN109912606A (en) * 2019-04-16 2019-06-21 新乡医学院 A kind of synthetic method of pyrimido indazole compounds
CN111484499A (en) * 2020-06-12 2020-08-04 南京欣久医药科技有限公司 Method for preparing drug intermediate chromene pyrimido indazolone derivative through catalysis

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Title
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Unusual rearrangement of imidazo[1,5-a]imidazoles and imidazo[1,2-b]pyrazoles into imidazo[1,5-a]pyrimidines and pyrazolo[1,5-a]pyrimidines;Khadija Gambouz，等;《RSC Advances》;20191231;第9卷(第50期);第24610-24616页 *

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