CN106967077A - A kind of chromene simultaneously [2,3 b] quinoline and its preparation method and application - Google Patents

A kind of chromene simultaneously [2,3 b] quinoline and its preparation method and application Download PDF

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CN106967077A
CN106967077A CN201710352936.4A CN201710352936A CN106967077A CN 106967077 A CN106967077 A CN 106967077A CN 201710352936 A CN201710352936 A CN 201710352936A CN 106967077 A CN106967077 A CN 106967077A
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quinoline
chromene
formaldehyde
hydroresorcinol
derivatives
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CN106967077B (en
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林伟
蔡琦
胡秀秀
王雅珍
王赟
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Jiangsu University of Technology
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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D491/00Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04Ortho-condensed systems
    • C07D491/044Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/052Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being six-membered

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Abstract

A kind of chromene simultaneously [2,3 b] quinoline, structure shown in its structural formula as I:Wherein, R1For H, CH3O, Cl or (CH3)3Any one in C;R2For H or CH3;R3For H, CH3Or Ph.The derivative is with formaldehyde of 2 chloroquinoline 3 or derivatives thereof, malononitrile and 1, and 3 cyclohexanediones or derivatives thereof are raw material, one-step synthesis.Synthesis route is simple and direct, mild condition, and total recovery is up to more than 61%.The compound that the present invention is provided confirms that there is preferably external Inhibit proliferaton to act on to human body hepatoma cell line HepG2 through pharmacological evaluation, with the effect for suppressing growth of tumour cell, can be applied in antineoplastic is prepared.

Description

A kind of chromene simultaneously [2,3-b] quinoline and its preparation method and application
Technical field
The invention belongs to technical field of organic synthesis, it is related to the preparation method of chromene simultaneously [2,3-b] quinoline, and Application in antineoplastic
Background technology
Chromene, also known as chromene, its skeleton are widely present in natural products, for example:Vitamin E, flavones, isoflavones Deng all contain chromene skeleton.Chromene derivative has extensive biological and pharmacological activity.Existing antiallergy and anticancer isoreactivity side The report in face.
Quinoline, is also benzo pyridine or azanaphthalene, is the very important nitrogen-containing heterocycle compound of a class, especially in pharmacy work Had a wide range of applications in industry.Moreover, they are also the parent nucleus of many natural products and biologically active drug structure, such as:Chlorine The peaceful alkali of quinoline, camel, camptothecine.By the continuous research of medicine scholar, substantial amounts of quinoline derivatives are synthesized, and it Have extensive bioactivity, for example:Anti-malarial, antibacterial, anti-inflammatory, antitumor, anti-diabetic, anti-asthma, anti-hypertension, Anti- alzheimer that disease, platelet aggregation-against, AntiHIV1 RT activity isoreactivity.
Simultaneously quinoline is the important fused heterocyclic compound of a class to chromene, with extensive bioactivity, in medicine Thing chemical field has important application value.For example:Simultaneously [4,3-b] quinoline can be female as beta-selective for 6H- chromenes Androgen receptor ligand.Further, since it has a very strong photoluminescent property, chromene and quinoline can also be applied to it is biological into Picture.There is document report that there is the derivatives such as the chromene and quinoline of spirane structure to have good antitumor activity recently, as a result table Such bright compound has cytotoxic activity to breast cancer, cervical carcinoma.So, design and synthesize some structures novelty has color Simultaneously quinoline has certain meaning to alkene.
The content of the invention
It is an object of the invention to provide a kind of synthesis of new chromene simultaneously [2,3-b] quinoline, through extracorporeal anti-tumor Active testing, such compound has preferable antitumor activity.
A kind of chromene simultaneously [2,3-b] quinoline, structure shown in its structural formula as I:
Wherein, R1For H, CH3O, Cl or (CH3)3Any one in C;R2For H or CH3;R3For H, CH3Or Ph.
It is a kind of such as the synthetic method of chromene simultaneously [2,3-b] quinoline, with 2- chloroquinoline -3- formaldehyde or derivatives thereof, Malononitrile and 1, hydroresorcinol or derivatives thereof be raw material, the compound shown in one-step synthesis Formulas I, its reaction equation is such as Under:
Described 2- chloroquinoline -3- formaldehyde derivatives are the chloro- 6- methoxy quinolines -3- formaldehyde of 2-, 2,6- dichloroquinolines -3- Any one in formaldehyde and the chloro- 6- tert-butyl groups quinoline-3-formaldehydes of 2-;Described hydroresorcinol derivative is 5,5- diformazans Any of base-hydroresorcinol, 5- phenyl-hydroresorcinol.
The solvent of reaction is acetonitrile, tetrahydrofuran, toluene, ethylene glycol, N,N-dimethylformamide (DMF), water and ethanol Any of, wherein preferred alcohol.The catalyst of reaction can be alkali, for example sodium hydroxide, sodium carbonate, cesium carbonate, hexahydro Pyridine or acid, such as p-methyl benzenesulfonic acid, acetic acid either organic micromolecule catalyst such as L-PROLINE.Preferably L- Proline.
Mole of 2- chloroquinoline -3- formaldehyde or derivatives thereof, malononitrile, hydroresorcinol or derivatives thereof and catalyst Than for 1:1:1:0.1~0.6.It is preferred that 1:1:1:0.5.Reaction is carried out in microwave reactor, and the temperature of reaction is 80~110 DEG C, preferably 100 DEG C, the effect of microwave can accelerate reaction.
It is preferred that, 2- chloroquinoline -3- formaldehyde, malononitrile and 1, hydroresorcinol is catalyst in microwave using L-PROLINE Under radiation, 100 DEG C are reacted 20 minutes, and the mol ratio of raw material is 2- chloroquinoline -3- formaldehyde:Malononitrile:Hydroresorcinol:L- dried meat Propylhomoserin=1:1:1:0.5.
The chromene that the present invention is synthesized simultaneously [2,3-b] quinoline, is a kind of compound of quite stable, these compounds There is preferably external Inhibit proliferaton effect to human body hepatoma cell line HepG2, show by anti tumor activity in vitro test, Most compounds have obvious antitumor activity, and wherein compound Ic, Id, Ig, Ii has good antitumor activity, it IC50Value is as follows:
Beneficial effect:The synthesis route of the present invention is simple and direct, mild condition, and total recovery is up to more than 61%, and the present invention is carried For chromene, simultaneously [2,3-b] quinoline confirms have to human body hepatoma cell line HepG2 preferably in vitro through pharmacological evaluation Inhibit proliferaton is acted on, and with the effect for suppressing growth of tumour cell, can be applied in antineoplastic is prepared.
Embodiment
Embodiment 1
By 2- chloroquinoline -3- formaldehyde (0.2mmol), malononitrile (0.2mmol) and 5,5- dimethyl-hydroresorcinol (0.2mmol) is added in 5mL microwave reaction pipes, is added L-PROLINE (0.1mmol) and ethanol 2mL, will be reacted the seal of tube, Stir 10 seconds in advance, mixture is reacted 30 minutes under microwave radiation in 100 DEG C, and after reaction terminates, reaction system is cooled to Room temperature, suction filtration is carried out after solid is separated out, then is carried out with the mixed solvent of DMF and water being recrystallized to give 2- (3,3- dimethyl -1- Oxo -2,3,4,12- tetrahydro -1H- chromenes simultaneously [2,3-b] quinoline -12- bases) malononitrile (Ia):Yield 71%;m.p.:248- 250℃;IR(KBr,ν,cm-1):3047,2920,2254,1622,1598,1448,1399,1215,1091,1055,1027, 999,752,689;1H NMR(400MHz,DMSO-d6)(δ,ppm):8.71 (s, 1H, ArH), 8.07 (d, J=7.6Hz, 1H, ), ArH 7.94 (d, J=8.4Hz, 1H, ArH), 7.88-7.84 (m, 1H, ArH), 7.67-7.63 (m, 1H, ArH), 5.23 (d, J =4.0Hz, 1H, CH), 5.00 (d, J=4.0Hz, 1H, CH), 2.81 (d, J=18.0Hz, 1H, CH), 2.68 (d, J= 18.0Hz, 1H, CH), 2.48 (d, J=16.0Hz, 1H, CH), 2.35 (d, J=16.0Hz, 1H, CH), 1.16 (s, 3H, CH3), 1.14(s,3H,CH3)。
Embodiment 2
According to the method for embodiment 1,2- chloroquinoline -3- formaldehyde is changed into 6- methoxyl group -2- chloroquinoline -3- formaldehyde, with L- Proline is catalyst, is reacted 30 minutes under microwave radiation, target product 2- is recrystallized to give with DMF and water mixed solvent (9- methoxyl group -3,3- dimethyl -1- oxo -2,3,4,12- tetrahydro -1H- chromenes simultaneously [2,3-b] quinoline -12- bases) malononitrile (Ib):Yield 74%;m.p.:268-270℃;IR(KBr,ν,cm-1):2896,2254,1635,1613,1466,1356, 1238,1216,1142,1112,1029,834;1H NMR(400MHz,DMSO-d6)(δ,ppm):8.57(s,1H,ArH),7.84 (d, J=9.2Hz, 1H, ArH), 7.51-7.48 (m, 1H, ArH), 7.45 (d, J=2.4Hz, 1H, ArH), 5.20 (d, J= 4.0Hz, 1H, CH), 4.97 (d, J=3.6Hz, 1H, CH), 3.93 (s, 3H, CH3), O 2.79 (d, J=17.6Hz, 1H, CH), 2.65 (d, J=17.2Hz, 1H, CH), 2.45 (d, J=16.4Hz, 1H, CH), 2.33 (d, J=16.4Hz, 1H, CH), 1.15 (s,3H,CH3),1.13(s,3H,CH3)。
Embodiment 3
According to the method for embodiment 1,2- chloroquinoline -3- formaldehyde is changed into the 6- tert-butyl group -2- chloroquinoline -3- formaldehyde, with L- Proline is catalyst, is reacted 30 minutes under microwave radiation, target product 2- is recrystallized to give with DMF and water mixed solvent (the 9- tert-butyl group -3,3- dimethyl -1- oxo -2,3,4,12- tetrahydro -1H- chromenes simultaneously [2,3-b] quinoline -12- bases) malononitrile (Ic):Yield 75%;m.p.:228-230℃;IR(KBr,ν,cm-1):2960,2937,2254,1642,1611,1439, 1394,1346,1265,1236,1212,1174,1145,1118,1024,997,831;1HNMR(400MHz,DMSO-d6)(δ, ppm):8.68 (s, 1H, ArH), 8.01-7.89 (m, 3H, ArH), 5.25 (d, J=3.6Hz, 1H, CH), 4.99 (d, J= 3.6Hz, 1H, CH), 2.81 (d, J=18.0Hz, 1H, CH), 2.52 (d, J=18.8Hz, 2H, CH2), 2.36 (d, J= 16.0Hz,1H,CH),1.41(s,9H,(CH3)3C)。
Embodiment 4
According to the method for embodiment 1,2- chloroquinoline -3- formaldehyde is changed into 2,6- dichloroquinoline -3- formaldehyde, with L-PROLINE For catalyst, reacted 30 minutes under microwave radiation, being recrystallized to give target product 2- with DMF and water mixed solvent, (9- is chloro- 3,3- dimethyl -1- oxo -2,3,4,12- tetrahydro -1H- chromenes simultaneously [2,3-b] quinoline -12- bases) malononitrile (Id):Yield 70%;m.p.:264-266℃;IR(KBr,ν,cm-1):2901,2257,1637,1345,1232,1212,1024,993,827, 763;1H NMR(400MHz,DMSO-d6)(δ,ppm):8.69 (s, 1H, ArH), 8.25 (d, J=2.4Hz, 1H, ArH), 7.96 (d, J=9.2Hz, 1H, ArH), 7.89-7.86 (m, 1H, ArH), 5.23 (d, J=4.4Hz, 1H, CH), 5.00 (d, J= 4.0Hz, 1H, CH), 2.80 (d, J=18.0Hz, 1H, CH), 2.67 (d, J=18.0Hz, 1H, CH), 2.47 (d, J= 16.4Hz, 1H, CH), 2.34 (d, J=16.4Hz, 1H, CH), 1.15 (s, 3H, CH3),1.13(s,3H,CH3)。
Embodiment 5
According to the method for embodiment 1, by 5,5- dimethyl -1, hydroresorcinol changes 1, hydroresorcinol, with L- dried meat ammonia into Acid is catalyst, is reacted 30 minutes under microwave radiation, target product 2- (1- are recrystallized to give with DMF and water mixed solvent Oxo -2,3,4,12- tetrahydro -1H- chromenes simultaneously [2,3-b] quinoline -12- bases) malononitrile (Ie):Yield 75%;m.p.:272- 274℃;IR(KBr,ν,cm-1):2930,2253,1656,1634,1498,1240,1214,1184,1048,1024,789, 764;1H NMR(400MHz,DMSO-d6)(δ,ppm):8.71 (s, 1H, ArH), 8.07 (d, J=8.0Hz, 1H, ArH), 7.94 (d, J=8.4Hz, 1H, ArH), 7.88-7.84 (m, 1H, ArH), 7.67-7.63 (m, 1H, ArH), 5.14 (d, J=4.0Hz, 1H, CH), 5.00 (d, J=3.6Hz, 1H, CH), 2.85-2.82 (m, 2H, CH2),2.49-2.43(m,2H,CH2),2.15- 1.97(m,2H,CH2)。
Embodiment 6
According to the method for embodiment 2, by 5,5- dimethyl -1, hydroresorcinol changes 1, hydroresorcinol, with L- dried meat ammonia into Acid is catalyst, is reacted 30 minutes under microwave radiation, target product 2- (9- are recrystallized to give with DMF and water mixed solvent Methoxyl group -1- oxo -2,3,4,12- tetrahydro -1H- chromenes simultaneously [2,3-b] quinoline -12- bases) malononitrile (If):Yield 73%; m.p.:278-280℃;IR(KBr,ν,cm-1):2912,2254,1629,1614,1504,1457,1398,1358,1218, 1142,1025,1002,829,785;1H NMR(400MHz,DMSO-d6)(δ,ppm):8.57 (s, 1H, ArH), 7.84 (d, J= 9.2Hz, 1H, ArH), 7.51-7.48 (m, 1H, ArH), 7.45 (d, J=2.8Hz, 1H, ArH), 5.11 (d, J=4.0Hz, 1H, ), CH 4.97 (d, J=3.6Hz, 1H, CH), 3.92 (s, 3H, CH3O),2.84-2.82(m,2H,CH2),2.49-2.47(m,2H, CH2),2.15-1.96(m,2H,CH2)。
Embodiment 7
According to the method for embodiment 3, by 5,5- dimethyl -1, hydroresorcinol changes 1, hydroresorcinol, with L- dried meat ammonia into Acid is catalyst, is reacted 30 minutes under microwave radiation, target product 2- (9- are recrystallized to give with DMF and water mixed solvent The tert-butyl group -1- oxo -2,3,4,12- tetrahydro -1H- chromenes simultaneously [2,3-b] quinoline -12- bases) malononitrile (Ig):Yield 73%; m.p.:246-248℃;IR(KBr,ν,cm-1):2956,2931,2257,1639,1504,1393,1236,1211,1185, 1047,1023,995,831,763;1H NMR(400MHz,DMSO-d6)(δ,ppm):8.66(s,1H,ArH),8.00-7.97 (m, 1H, ArH), 7.93 (d, J=2.0Hz, 1H, ArH), 7.87 (d, J=8.8Hz, 1H, ArH), 5.12 (d, J=3.6Hz, 1H, CH), 4.97 (d, J=3.6Hz, 1H, CH), 2.84-2.81 (m, 2H, CH2),2.48-2.46(m,2H,CH2),2.14- 1.99(m,2H,CH2),1.40(s,9H,(CH3)3C)。
Embodiment 8
According to the method for embodiment 4, by 5,5- dimethyl -1, hydroresorcinol changes 1, hydroresorcinol, with L- dried meat ammonia into Acid is catalyst, is reacted 30 minutes under microwave radiation, target product 2- (9- are recrystallized to give with DMF and water mixed solvent Chloro- 1- oxos -2,3,4,12- tetrahydro -1H- chromenes simultaneously [2,3-b] quinoline -12- bases) malononitrile (Ih):Yield 68%; m.p.:292-294℃;IR(KBr,ν,cm-1):2895,2256,1630,1486,1391,1341,1234,1185,1024, 995,921,827;1H NMR(400MHz,DMSO-d6)(δ,ppm):8.68(s,1H,ArH),8.24(s,1H,ArH),7.96- 7.93(m,1H,ArH),7.88-7.84(m,1H,ArH),5.14-5.12(m,1H,CH),5.01-4.96(m,1H,CH), 2.89-2.92(m,4H,2×CH2),2.15-1.96(m,2H,CH2)。
Embodiment 9
According to the method for embodiment 1, by 5,5- dimethyl -1, hydroresorcinol changes 5- phenyl -1 into, hydroresorcinol, with L-PROLINE is catalyst, is reacted 30 minutes under microwave radiation, target product is recrystallized to give with the mixed solvent of DMF and water 2- (1- oxo -3- phenyl -2,3,4,12- tetrahydro -1H- chromenes simultaneously [2,3-b] quinoline -12- bases) malononitrile (Ii):Yield 64%;m.p.:226-228℃;IR(KBr,ν,cm-1):2936,2257,1636,1497,1397,1240,1203,1024, 993,761;1H NMR(400MHz,CDCl3)(δ,ppm):8.75-8.73 (m, 1H, ArH), 8.09 (d, J=8.4Hz, 1H, ), ArH 7.95 (d, J=8.0Hz, 1H, ArH), 7.89-7.85 (m, 1H, ArH), 7.68-7.64 (m, 1H, ArH), 7.47- 7.34(m,4H,ArH),7.31-7.25(m,1H,ArH),5.18-5.13(m,1H,CH),5.08-5.05(m,1H,CH), 3.67-3.50(m,1H,CH),3.26-3.13(m,1H,CH),3.06-2.99(m,1H,CH),2.88-2.74(m,1H,CH), 2.68-2.63(m,1H,CH)。
Embodiment 10
According to the method for embodiment 3, by 5,5- dimethyl -1, hydroresorcinol changes 5- phenyl -1 into, hydroresorcinol, with Hexahydropyridine is catalyst, is reacted 30 minutes under microwave radiation, target product is recrystallized to give with the mixed solvent of DMF and water 2- (the 9- tert-butyl group -1- oxo -3- phenyl -2,3,4,12- tetrahydro -1H- chromenes simultaneously [2,3-b] quinoline -12- bases) malononitrile (Ij):Yield 67%;m.p.:248-250℃;IR(KBr,ν,cm-1):2963,2933,2255,1638,1502,1418, 1366,1239,1205,1123,1098,1025,999,947,833;1H NMR(400MHz,DMSO-d6)(δ,ppm):8.73- 8.72(m,1H,ArH),8.04-7.91(m,3H,ArH),7.50-7.30(m,5H,ArH),5.20-5.15(m,1H,CH), 5.09-5.05(m,1H,CH),3.70-3.53(m,1H,CH),3.26-3.16(m,1H,CH),3.08-3.02(m,1H,CH), 2.95-2.88(m,1H,CH),2.71-2.66(m,1H,CH),1.44(s,9H,(CH3)3C)。
Embodiment 11
According to the method for embodiment 4, by 5,5- dimethyl -1, hydroresorcinol changes 5- phenyl -1 into, hydroresorcinol, with P-methyl benzenesulfonic acid is catalyst, is reacted 30 minutes under microwave radiation, and target production is recrystallized to give with DMF and water mixed solvent Thing 2- (the chloro- 1- oxos -3- phenyl -2,3,4,12- tetrahydros -1H- chromenes of 9- simultaneously [2,3-b] quinoline -12- bases) malononitrile (Ik):Yield 69%;m.p.:270-272℃;IR(KBr,ν,cm-1):2902,2256,1639,1492,1454,1444, 1234,1200,1024,997,839,762;1H NMR(400MHz,CDCl3)(δ,ppm):8.73-8.71(m,1H,ArH), 8.27-7.86(m,1H,ArH),7.98-7.96(m,1H,ArH),7.89-7.86(m,1H,ArH),7.47-7.34(m,4H, ArH),7.31-7.25(m,1H,ArH),5.19-5.14(m,1H,CH),5.08-5.05(m,1H,CH),3.67-3.50(m, 1H,CH),3.26-3.11(m,1H,CH),3.06-2.98(m,1H,CH),2.87-2.77(m,1H,CH),2.68-2.63(m, 1H,CH)。

Claims (9)

1. a kind of chromene simultaneously [2,3-b] quinoline, structure shown in its structural formula as I:
Wherein, R1For H, CH3O, Cl or (CH3)3Any one in C;R2For H or CH3;R3For H, CH3Or Ph.
2. the synthetic method of a kind of chromene as claimed in claim 1 simultaneously [2,3-b] quinoline, it is characterised in that with 2- Chloroquinoline -3- formaldehyde or derivatives thereof, malononitrile and 1, hydroresorcinol or derivatives thereof are raw material, shown in one-step synthesis Formulas I Compound, its reaction equation is as follows:
3. the synthetic method of chromene as claimed in claim 2 simultaneously [2,3-b] quinoline, it is characterised in that described 2- Chloroquinoline -3- formaldehyde derivatives are the chloro- 6- methoxy quinolines -3- formaldehyde of 2-, 2,6- dichloroquinoline -3- formaldehyde and chloro- uncles 6- of 2- Any one in butyl quinoline-3-formaldehyde;Described hydroresorcinol derivative is 5,5- dimethyl -1,3- hexamethylenes two Any of ketone, 5- phenyl-hydroresorcinol.
4. the synthetic method of chromene as claimed in claim 2 simultaneously [2,3-b] quinoline, it is characterised in that reaction it is molten Agent is any of acetonitrile, tetrahydrofuran, toluene, ethylene glycol, N,N-dimethylformamide, water and ethanol.
5. the synthetic method of chromene as claimed in claim 2 simultaneously [2,3-b] quinoline, it is characterised in that reaction is urged Agent is any one in sodium hydroxide, sodium carbonate, cesium carbonate, hexahydropyridine, p-methyl benzenesulfonic acid, acetic acid and L-PROLINE or several Kind.
6. the synthetic method of chromene as claimed in claim 5 simultaneously [2,3-b] quinoline, it is characterised in that 2- chloroquinolines- The mol ratio of 3- formaldehyde or derivatives thereof, malononitrile, hydroresorcinol or derivatives thereof and catalyst is 1:1:1:0.1~ 0.6。
7. the synthetic method of chromene as claimed in claim 2 simultaneously [2,3-b] quinoline, it is characterised in that reaction is micro- Carried out in ripple reactor, the temperature of reaction is 80~110 DEG C.
8. the synthetic method of chromene as claimed in claim 2 simultaneously [2,3-b] quinoline, it is characterised in that 2- chloroquinolines- 3- formaldehyde, malononitrile and 1, hydroresorcinol, by catalyst of L-PROLINE under microwave radiation, 100 DEG C are reacted 20 minutes, former The mol ratio of material is 2- chloroquinoline -3- formaldehyde:Malononitrile:Hydroresorcinol:L-PROLINE=1:1:1:0.5.
9. a kind of simultaneously application of [2,3-b] quinoline in antineoplastic is prepared of chromene as claimed in claim 1.
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