CN110003089A - A kind of 3- methylol -9- substituted carbazole and preparation method thereof - Google Patents

A kind of 3- methylol -9- substituted carbazole and preparation method thereof Download PDF

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CN110003089A
CN110003089A CN201910160754.6A CN201910160754A CN110003089A CN 110003089 A CN110003089 A CN 110003089A CN 201910160754 A CN201910160754 A CN 201910160754A CN 110003089 A CN110003089 A CN 110003089A
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methylol
carbazole
preparation
substituted carbazole
dehydrated alcohol
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CN110003089B (en
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刘玉婷
杨岚
尹大伟
党阳
邹倩
李洁
孙嘉希
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Shaanxi University of Science and Technology
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system

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  • Organic Chemistry (AREA)
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Abstract

The present invention provides a kind of preparation methods of 3- methylol -9- substituted carbazole.In dry 100mL three-necked flask, A mL DMSO, B mol paraformaldehyde, C mol sodium ethoxide, D mL dehydrated alcohol are sequentially added under ice salt bath is cooling, stirring, after solid dissolution, quickly instill the DMSO solution of E mol N- alkyl carbazole, A:E=(100 ~ 300): 1, C:D=1:8, B:C:E=1:1.5:1 is reacted after reacting 3 min with the termination of a few drop concentrated hydrochloric acids.Then distilled water is added, there is solid precipitation, filters, wash, be drying to obtain crude product.Crude product recrystallizes to obtain sterling 3- methylol -9- substituted carbazole with dehydrated alcohol.Operation of the present invention is simple, and the reaction time is short, and product purity is high, and yield is high, and reaction condition is mild, safety and environmental protection, and the synthesis and development to such compound are significant.

Description

A kind of 3- methylol -9- substituted carbazole and preparation method thereof
Technical field
The invention belongs to the field of chemical synthesis, in particular to 3- methylol -9- substituted carbazole and preparation method thereof.
Background technique
Carbazole is a kind of nitrogenous aromatic heterocycle compound with rigid conjugate planes structure, and molecular skeleton is easy to introduce The functional group of various functionalization, can be as antimicrobial, fluorescent material etc..Carbazole and its derivative have been widely used for The fields such as medicine, fuel, high molecular material.
Existing aldehyde -ol restoring method introduces methylol, and experiment condition requires harsh, poor selectivity, and expensive. So developing a kind of method that process is easy, yield prepares 3- methylol -9- substituted carbazole has certain meaning high, inexpensively Justice.
Summary of the invention
The purpose of the present invention is to provide a kind of preparation method for preparing 3- methylol -9- substituted carbazole, this method has The advantage that easy to operate, safety, yield are high, reaction condition is mild, the reaction time is short.
In order to achieve the above objectives, the technical solution adopted by the present invention are as follows:
The general structure of 3- methylol -9- substituted carbazole are as follows:
Wherein R is CH3, C2H5, C3H7- n, C12H25- n, C14H29- n, C16H33-n.
The preparation method of 3- methylol -9- substituted carbazole, comprising the following steps:
In dry 100mL three-necked flask, sequentially added under ice salt bath is cooling A mL DMSO, B mol paraformaldehyde, C mol sodium ethoxide, D mL dehydrated alcohol, stirring quickly instill the DMSO solution of E mol N- alkyl carbazole after solid dissolution, A:E=(100~300): 1, C:D=1:8, B:C:E=1:1.5:1 are reacted after reacting 3 min with the termination of a few drop concentrated hydrochloric acids.So After distilled water is added, have solid precipitation, filter, wash, be drying to obtain crude product.Crude product recrystallizes to obtain sterling 3- with dehydrated alcohol Methylol -9- substituted carbazole.
The general structure of the N- alkyl carbazole are as follows:
Wherein R is CH3, C2H5, C3H7- n, C12H25- n, C14H29- n, C16H33-n.
The addition distilled water, DMSO dosage are A mL, distilled water: DMSO=1.5:1.
A few drop concentrated hydrochloric acids are 3 drops.
Compared with the existing technology, the invention has the benefit that
Carbazole enhances its electron rich because of the presence of No. 9 position N, and introduces methylols No. 3 positions, provides one The intermediate of high activity can obtain the derivative with bigger π-electron-conjugated system to continue to introduce other groups.
The preparation method of 3- methylol -9- substituted carbazole provided by the invention is original with N- alkyl carbazole and paraformaldehyde Material, sodium ethoxide make solvent as catalyst, with DMSO, can be prepared by 3- methylol -9- substituted carbazole in the short time.This method Reaction condition is mild, and the reaction time is short, and yield is high, and post-processes simply, and product purity is high, has great application prospect.
Detailed description of the invention
Fig. 1 is the IR spectrogram of 3- methylol -9- methyl carbazole prepared by embodiment 1
Fig. 2 is the IR spectrogram of 3- methylol -9- ethyl carbazole prepared by embodiment 2
Fig. 3 is the IR spectrogram of 3- methylol -9- propyl carbazole prepared by embodiment 3
Fig. 4 is the IR spectrogram of 3- methylol -9- dodecyl carbazole prepared by embodiment 4
Fig. 5 is the IR spectrogram of 3- methylol -9- myristyl carbazole prepared by embodiment 5
Fig. 6 is the IR spectrogram of 3- methylol -9- cetyl carbazole prepared by embodiment 6
Fig. 7 is 3- methylol -9- methyl carbazole prepared by embodiment 11HNMR spectrogram
Fig. 8 is 3- methylol -9- ethyl carbazole prepared by embodiment 21HNMR spectrogram
Fig. 9 is 3- methylol -9- propyl carbazole prepared by embodiment 31HNMR spectrogram
Figure 10 is 3- methylol -9- dodecyl carbazole prepared by embodiment 41HNMR spectrogram
Figure 11 is 3- methylol -9- myristyl carbazole prepared by embodiment 51HNMR spectrogram
Figure 12 is 3- methylol -9- cetyl carbazole prepared by embodiment 61HNMR spectrogram
Specific embodiment
It is that example is combined to be described in further details the present invention below:
The present invention is using N- alkyl carbazole and paraformaldehyde as raw material, and DMSO is solvent, and sodium ethoxide is as catalyst, in short-term It is interior to prepare a series of 3- methylol -9- substituted carbazoles.Its reaction equation is as follows:
Wherein R is CH3, C2H5, C3H7- n, C12H25- n, C14H29- n, C16H33-n.
The preparation of 1 3- methylol -9- methyl carbazole of embodiment:
In dry 100mL three-necked flask, 20mL DMSO, 84mg (2.8mmol) are sequentially added under ice salt bath is cooling Paraformaldehyde, 285.8mg (4.2mmol) sodium ethoxide, 2mL dehydrated alcohol, stirring and dissolving, by 500mg (2.8mmol) N- methyl Carbazole is dissolved in 5mLDMSO, is quickly instilled in reaction system, after reacting 3min, 3 drop concentrated hydrochloric acids is added dropwise and terminate reaction.Then plus Enter 30mL distilled water, there is solid precipitation, filters, washes, is drying to obtain crude product.Crude product recrystallizes to obtain sterling Huang with dehydrated alcohol Color solid 3- methylol -9- methyl carbazole.Yield 90.7%, 87.9~91.2 DEG C of fusing point.
IR (KBr) v:3400 (- OH), 3047 (phenyl ring C-H), 2931,2881 (saturation C-H), 1600,1475 (phenyl ring bones Frame vibration), 1411 (- CH3Bending vibration), 1325 (C-N)
1H NMR(400MHz,DMSO):δ8.08(t,2H),7.52(t,2H),7.45(t,2H),7.19(t,1H), 5.16(t,1H),4.67(d,2H),3.86(s,3H).
The preparation of 2 3- methylol -9- ethyl carbazole of embodiment
In dry 100mL three-necked flask, 20mL DMSO, 78mg (2.6mmol) are sequentially added under ice salt bath is cooling Paraformaldehyde, 265mg (3.9mmol) sodium ethoxide, 2mL dehydrated alcohol, stirring and dissolving, by 500mg (2.6mmol) N- ethyl click Azoles is dissolved in 5mLDMSO, is quickly instilled in reaction system, after reacting 3 min, 3 drop concentrated hydrochloric acids is added dropwise and terminate reaction.Then it is added 30mL distilled water has solid precipitation, filters, washes, is drying to obtain crude product.Crude product recrystallizes to obtain sterling yellow with dehydrated alcohol Solid 3- methylol -9- ethyl carbazole.Yield 81.4%, 70.5~75.1 DEG C of fusing point.
IR (KBr) v:3402 (- OH), 3047 (phenyl ring C-H), 2976,2866 (saturation C-H), 1600,1465 (phenyl ring bones Frame vibration), 1377 (- CH3Bending vibration), 1328 (C-N)
1H NMR(400MHz,DMSO):δ8.11(t,2H),7.53(t,2H),7.43(t,2H),7.18(t,1H), 5.19(t,1H),4.69(d,2H),4.40(d,2H),1.28(s,3H).
The preparation of 3 3- methylol -9- propyl carbazole of embodiment
It is more that 20mL DMSO, 72mg (2.4mmol) are sequentially added in dry 100mL three-necked flask, under ice salt bath is cooling Polyformaldehyde, 245mg (3.6mmol) sodium ethoxide, 2mL dehydrated alcohol, stirring and dissolving, by 500mg (2.4mmol) N- propyl carbazole It is dissolved in 5mLDMSO, quickly instills in reaction system, after reacting 3 min, 3 drop concentrated hydrochloric acids are added dropwise and terminate reaction.Then it is added 30mL distilled water has solid precipitation, filters, washes, is drying to obtain crude product.Crude product recrystallizes to obtain sterling yellow with dehydrated alcohol Solid 3- methylol -9- propyl carbazole.Yield 77.5%, m.p.:94.3~95.0 DEG C.
IR (KBr) v:3386 (- OH), 3039 (phenyl ring skeletal vibrations), 2923,2877 (saturation C-H), 1602,1465 (phenyl ring skeletal vibration), 1377 (- CH3Bending vibration), 1328 (C-N)
1H NMR(400MHz,DMSO):δ8.08-8.12(t,1H),7.54(q,2H),7.42(t,2H),7.17(t, 1H), 5.14(s,1H),4.65(s,2H),4.34(t,2H),1.78(t,2H),0.85(s,3H)。
The preparation of 4 3- methylol of embodiment-dodecyl carbazole
In dry 100mL three-necked flask, 20mL DMSO, 45mg (1.5mmol) are sequentially added under ice salt bath is cooling Paraformaldehyde, 153mg (2.25mmol) sodium ethoxide, 1mL dehydrated alcohol, stirring and dissolving, by 500mg (1.5mmol) N- dodecane Base carbazole is dissolved in 5mLDMSO, is quickly instilled in reaction system, after reacting 3min, 3 drop concentrated hydrochloric acids is added dropwise and terminate reaction.Then 30mL distilled water is added, has solid precipitation, filters, washes, is drying to obtain crude product.Crude product recrystallizes to obtain sterling with dehydrated alcohol White solid 3- methylol -9- dodecyl carbazole.Yield 84.3%, m.p.:65-66 DEG C.
IR (KBr) v:3269 (- OH), 3055 (phenyl ring C-H), 2920,2850 (saturation C-H), 1602,1469 (phenyl ring bones Frame vibration), 1336 (- CH3 bending vibrations), 1001 (primary alconol C-O)
1H NMR(400MHz,DMSO)δ8.21-8.01(m,2H),7.66-7.49(m,2H),7.43(t, 2H),7.17 (t,1H),5.17(t,1H),4.65(d,2H),4.37(t,2H),1.75(s,2H),1.34-1.07(m, 18H),0.85(t, 3H).
The preparation of 5 3- methylol -9- myristyl carbazole of embodiment
In dry 100mL three-necked flask, 20mL DMSO, 42mg (1.4mmol) are sequentially added under ice salt bath is cooling Paraformaldehyde, 143mg (2.1mmol) sodium ethoxide, 1mL dehydrated alcohol, stirring and dissolving, by 500mg (1.4mmol) the N- tetradecane Base carbazole is dissolved in 5mLDMSO, is quickly instilled in reaction system, after reacting 3min, 3 drop concentrated hydrochloric acids is added dropwise and terminate reaction.Then 30mL distilled water is added, has solid precipitation, filters, washes, is drying to obtain crude product.Crude product recrystallizes to obtain sterling with dehydrated alcohol White solid 3- methylol -9- myristyl carbazole.Yield 79.2%, m.p.:62-62 DEG C.
IR (KBr) v:3267 (- OH), 3049 (phenyl ring C-H), 2920,2854 (saturation C-H), 1608,1471 (phenyl ring bones Frame vibration), 1348 (- CH3 bending vibrations), 1070 (primary alconol C-O)
1H NMR(400MHz,DMSO)δ8.09(m,2H),7.55(dd,2H),7.43(dd,2H),7.17 (t,1H), 5.15(t,1H),4.64(t,2H),4.37(t,2H),1.75(m,2H),1.22(dd,22H),0.85(t, 3H).
The preparation of 6 3- methylol -9- cetyl carbazole of embodiment
In dry 100mL three-necked flask, 20mL DMSO, 39mg (1.3mmol) are sequentially added under ice salt bath is cooling Paraformaldehyde, 133mg (1.95mmol) sodium ethoxide, 1mL dehydrated alcohol, stirring and dissolving, by 500mg (1.3mmol) N- hexadecane Base carbazole is dissolved in 5mLDMSO, is quickly instilled in reaction system, after reacting 3min, 3 drop concentrated hydrochloric acids is added dropwise and terminate reaction.Then 30mL distilled water is added, has solid precipitation, filters, washes, is drying to obtain crude product.Crude product recrystallizes to obtain sterling with dehydrated alcohol White solid 3- methylol -9- cetyl carbazole.Yield 88.5%, m.p.:59-60 DEG C.
IR (KBr) v:3325 (- OH), 3051 (phenyl ring C-H), 2918,2850 (saturation C-H), 1602,1471 (phenyl ring bones Frame vibration), 1336 (- CH3Bending vibration), 1006 (primary alconol C-O)
1H NMR(400MHz,DMSO)δ8.14(m,2H),7.58(dd,2H),7.45(t,2H),7.20(t,1H), 5.18(t,1H),4.68(d,2H),4.40(t,2H),1.78(s,2H),1.23(d,26H),0.88(t,3H)。

Claims (10)

1. a kind of 3- methylol -9- substituted carbazole, which is characterized in that structural formula are as follows:
In formula, R CH3、C2H5、C3H7-n、C12H25-n、C14H29- n or C16H33-n。
2. a kind of preparation method of 3- methylol -9- substituted carbazole, which comprises the steps of:
Under condition of ice bath, N- alkyl carbazole is reacted in DMSO solution by catalyst of sodium ethoxide with formaldehyde, obtains one kind 3- methylol -9- substituted carbazole.
3. a kind of preparation method of 3- methylol -9- substituted carbazole according to claim 2, which is characterized in that described N- substituted carbazole structural formula are as follows:
In formula, R CH3、C2H5、C3H7-n、C12H25-n、C14H29- n or C16H33-n。
4. a kind of preparation method of 3- methylol -9- substituted carbazole according to claim 2, which is characterized in that described Formaldehyde is paraformaldehyde.
5. a kind of preparation method of 3- methylol -9- substituted carbazole according to claim 2, which is characterized in that the N- After alkyl carbazole is configured to the DMSO solution of 0.1-0.2g/mL, instillation is dispersed in the DMSO solution of formaldehyde, sodium ethoxide, is started Reaction.
6. a kind of preparation method of 3- methylol -9- substituted carbazole according to claim 2, which is characterized in that also to The dehydrated alcohol for dissolving sodium ethoxide is added in DMSO, the concentration of sodium ethoxide in ethanol is 0.15g/mL.
7. a kind of preparation method of 3- methylol -9- substituted carbazole according to claim 2, which is characterized in that reaction is opened Begin that appropriate concentrated hydrochloric acid is added and terminates reaction after time 3min.
8. a kind of preparation method of 3- methylol -9- substituted carbazole according to claim 2, which is characterized in that reaction knot Shu Hou is added appropriate distilled water and product is enabled to be precipitated, filters, washes, is drying to obtain crude product；Crude product is recrystallized with dehydrated alcohol Sterling.
9. a kind of preparation method of 3- methylol -9- substituted carbazole according to claim 2, which is characterized in that formaldehyde, second Sodium alkoxide, N- alkyl carbazole molar ratio are 1:1.5:1.
10. a kind of preparation method of 3- methylol -9- substituted carbazole according to claim 2, which is characterized in that specific step Suddenly include:
In dry 100mL three-necked flask, A mL DMSO, B mol paraformaldehyde, C mol are sequentially added under ice salt bath is cooling Sodium ethoxide, D mL dehydrated alcohol, stirring quickly instill the DMSO solution of E mol N- alkyl carbazole, A:E=after solid dissolution (100~300): 1, C:D=1:8, B:C:E=1:1.5:1 are reacted after reacting 3min with the termination of a few drop concentrated hydrochloric acids；Reaction terminates Afterwards, appropriate distilled water, which is added, enables product be precipitated, and filters, washes, is drying to obtain crude product；Crude product recrystallizes pure with dehydrated alcohol Product.
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