CN110540516B - Preparation method of 1-sulfonylmethyl-3, 4-dihydronaphthalene - Google Patents

Preparation method of 1-sulfonylmethyl-3, 4-dihydronaphthalene Download PDF

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CN110540516B
CN110540516B CN201910489029.3A CN201910489029A CN110540516B CN 110540516 B CN110540516 B CN 110540516B CN 201910489029 A CN201910489029 A CN 201910489029A CN 110540516 B CN110540516 B CN 110540516B
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刘宇
王巧林
陈赞
唐课文
熊碧权
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Hunan Institute of Science and Technology
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    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C315/00Preparation of sulfones; Preparation of sulfoxides
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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D333/00Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/30Hetero atoms other than halogen
    • C07D333/34Sulfur atoms
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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D333/00Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/54Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
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    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00Systems containing two condensed rings
    • C07C2602/02Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04One of the condensed rings being a six-membered aromatic ring
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Abstract

The invention discloses a synthetic route for preparing 1-sulfonyl methyl substituted 3, 4-dihydronaphthalene compounds. Under the mediation of visible light, vinyl cyclopropane compounds and sulfonyl chloride react to synthesize 1-sulfonyl methyl substituted 3, 4-dihydronaphthalene compounds. The method has the advantages of mild reaction conditions, wide substrate application range, high yield of target products and the like.

Description

Preparation method of 1-sulfonylmethyl-3, 4-dihydronaphthalene
Technical Field
The application belongs to the technical field of organic synthesis, and particularly relates to a preparation method of 1-sulfonylmethyl-3, 4-dihydronaphthalene.
Background
Dihydronaphthalene compounds are very important structural units in organic synthesis and pharmaceutical synthesis, and methods for effectively synthesizing the compounds have attracted great attention of organic synthesis chemists. The inventors have long sought to develop novel synthetic strategies for dihydronaphthalene compounds to incorporate various building blocks to construct novel reaction products and enrich existing synthetic pathways (see 1)J. Org. Chem.201782147394-7401;2) J. Org. Chem.20188384657-4664, 3) CN 106946817B; 4) CN 108129287A; 5) CN109651210A, etc.).
Over the past few decades, the introduction of sulfur-containing building blocks, particularly sulfonyl groups, into organic molecules has attracted a great deal of attention from chemists. Among common sulfonyl sources, sulfonyl chloride is a cheap, abundant and easily available sulfonyl source, and the inventors have reported a synthesis strategy for constructing 2-sulfonyl 3, 4-dihydronaphthalene compounds by the reaction of sulfonyl chloride with methylene cyclopropane compounds under photocatalytic conditions (see 6) CN 109705001A):
Figure 327318DEST_PATH_IMAGE001
however, the prior art also widely reports that arylsulfonyl chlorides can be used under visible light mediated conditionsTo be used as an aryl radical source to participate in the construction of a series of organic synthesis reactions (see 7) derived cyclics of 1, 6-enzymes with aryl sulfonyl Chlorides by Using Visible-Light photothioredox Catalysts, Jin-heng Li et al, Angewandte Chemie International Edition, 2013; 8) Reusable Visible Light photothioredox Catalysts, and functionalized Benzylic C (sp. beta. aromatic C)3) H catalysis/Carbocyclation Reactions, Jin-heng Li et al, Synlett, 2012, etc.).
Aiwen Lei topic group reports a visible light-induced, oxidant-free oxidative cross-coupling reaction to build allylic sulfones from olefins and sulfinic acids, where the following reaction is disclosed in the study of the mechanism (see FIG. 9)Chem. Commun., 2016, 52, 10407--10410):
Figure 551626DEST_PATH_IMAGE002
The inventor conducts long-term intensive research and experimental investigation, and provides a visible light mediated C-C sigma-bond sulfonylation/arylation reaction, and a 1-sulfonylmethyl-substituted 3, 4-dihydronaphthalene compound is synthesized by the reaction of vinyl cyclopropane compounds and sulfonyl chloride.
Disclosure of Invention
The invention aims to enrich synthesis routes for preparing 1-sulfonylmethyl-substituted 3, 4-dihydronaphthalene compounds, and provides a novel method for synthesizing 1-sulfonylmethyl-substituted 3, 4-dihydronaphthalene compounds by reacting vinyl cyclopropane compounds and sulfonyl chloride under the mediation of visible light. The method has the advantages of mild reaction conditions, wide substrate application range, high yield of target products and the like.
The invention provides a novel method for preparing 1-sulfonyl methyl substituted 3, 4-dihydronaphthalene compounds,
Figure 878702DEST_PATH_IMAGE003
the method comprises the following steps:
the method comprises the steps of sequentially adding vinyl cyclopropane compounds shown in the formula I, sulfonyl chloride shown in the formula II, photocatalyst, alkali and an organic solvent into a Schlenk tube sealing reactor, then protecting the reactor with an inert atmosphere, placing the reactor in an oil bath kettle at 90-110 ℃ under the illumination condition, stirring and reacting for 12-36 hours, detecting the reaction completely through TLC and/or GC-MS, and carrying out post-treatment to obtain target products shown in the formula III.
Wherein in formula I and formula III, the structural units
Figure 225370DEST_PATH_IMAGE004
Is represented by C6-C20Aryl of (C)3-C20The heteroaryl group of (a); r1Representing a structural unit
Figure 637897DEST_PATH_IMAGE004
One or more substituents of the above, each R1The substituents are independently of one another selected from hydrogen, C1-C20Alkyl of (C)1-C20Alkoxy group of (C)6-C20Aryl, nitro, halogen, -CN;
in the formulae II and III, R2Is selected from C1-C20Alkyl, substituted or unsubstituted C6-C20Aryl of (C)3-C20The heteroaryl group of (a); and wherein the substituents in said "substituted or unsubstituted" are selected from halogen, C1-C6Alkyl of (C)1-C6Alkoxy group of (C)1-C6Haloalkyl, nitro, C1-C6Acyl group of-CN.
Preferably, in the formulae I and III, the structural units
Figure 400316DEST_PATH_IMAGE004
Is represented by C6-C14Aryl of (C)3-C12The heteroaryl group of (a); r1Representing a structural unit
Figure 581899DEST_PATH_IMAGE004
One or more substituents of the above, each R1The substituents are independently of one another selected from hydrogen, C1-C6Alkyl of (C)1-C6Alkoxy group of (C)6-C14Aryl, nitro, halogen, -CN;
in the formulae II and III, R2Is selected from C2-C12Alkyl, substituted or unsubstituted C6-C14Aryl of (C)3-C12The heteroaryl group of (a); and wherein the substituents in said "substituted or unsubstituted" are selected from halogen, C1-C6Alkyl of (C)1-C6Alkoxy group of (C)1-C6Haloalkyl, nitro, C1-C6Acyl group of-CN.
Most preferably, the compound of formula I is selected from compounds having the following structure:
Figure 37151DEST_PATH_IMAGE005
the compound of formula II is selected from compounds having the following structure:
Figure 2221DEST_PATH_IMAGE006
according to the method of the present invention, the photocatalyst is selected from Ru (bpy)3Cl2、Ir(ppy)3、Eosin Y、Na2-Eosin Y; preferably, the photocatalyst is selected from Ru (bpy)3Cl2
The aforementioned method according to the present invention, wherein the base is selected from 2, 6-lutidine, K2CO3、Na2CO3、Cs2CO3Any one of pyridine or triethylamine; preferably, the base is selected from 2, 6-lutidine.
The method according to the present invention, wherein the organic solvent is selected from any one of 1, 4-dioxane, THF, DMF, DMSO, toluene, and acetonitrile; preferably, the organic solvent is selected from 1, 4-dioxane.
In the aforementioned method according to the present invention, as for the "inert atmosphere", it is understood by those skilled in the art that the "inert atmosphere" is understood to be an atmosphere inert to the reaction, and is not mechanically considered to be an inert gas. The "inert atmosphere" may be an argon atmosphere, a nitrogen atmosphere, or the like. Preferably, the "inert atmosphere" is an argon atmosphere.
According to the aforementioned method of the present invention, the heteroatom in the heteroaryl group having the carbon number in any part may be selected from any one or more of N, S and O; as concrete examples of the heteroaryl group having the above-mentioned number of carbon atoms, thienyl, furyl, pyridyl, pyrrolyl and the like can be cited.
According to the method of the present invention, the illumination condition can be provided by a 5W blue LED lamp, a 3W blue LED lamp, a 36W fluorescent lamp or a 5W green LED lamp. Preferably a 5W blue LED lamp.
According to the method of the invention, the reaction time of the reaction is preferably 24 hours, and the reaction temperature is preferably 100 ℃.
According to the method, the molar ratio of the vinyl cyclopropane compound shown in the formula I, the sulfonyl chloride shown in the formula II, the photocatalyst and the alkali is 1: 1-3: 0.02-0.1: 1-3; preferably, the molar ratio of the vinyl cyclopropane compound shown in the formula I, the sulfonyl chloride shown in the formula II, the photocatalyst and the base is 1:2:0.05: 2.
The method according to the present invention, wherein the post-processing comprises the following operations: after the reaction, the reaction solution was filtered through a short column of silica gel, washed with ethyl acetate, the organic phase was washed with saturated brine, the aqueous phase was extracted with ethyl acetate, the organic phases were combined, and anhydrous Na was added2SO4Drying, concentrating under reduced pressure to remove solvent to obtain crude product, and purifying by silica gel column chromatography (eluting solvent is n-hexane/ethyl acetate) to obtain the target product.
Compared with the prior art, the invention has the following beneficial effects:
1) the invention reports a new method for synthesizing a 1-sulfonyl methyl substituted 3, 4-dihydronaphthalene compound by the reaction of a vinyl cyclopropane compound and sulfonyl chloride mediated by visible light for the first time;
2) the synthesis strategy of the invention has the advantages of easily available reaction raw material sources, mild reaction conditions, simple operation, recyclable catalyst, wide reaction substrate application range, high target product yield and the like.
Detailed Description
The present invention is described in further detail below with reference to specific examples:
examples 1-24 optimization of reaction conditions
The effect of different reaction conditions on the yield of the desired product (III-1, 1-benzenesulfonylmethyl-3, 4-dihydronaphthalene) was investigated using α -cyclopropylstyrene of formula I-1 and benzenesulfonyl chloride of formula II-1 as templates, representative examples are shown in examples 1-24:
Figure 568331DEST_PATH_IMAGE007
a typical experimental procedure for example 1 is as follows:
to a 25mL Schlenk closed-tube reactor, α -cyclopropylstyrene of the formula I-1 (0.2 mmol), benzenesulfonyl chloride of the formula II-1 (2.0 equiv, 0.4 mmol), Ru (bpy)3Cl2(5 mol%, 0.01 mmol) and 2, 6-dimethylpyridine (2 equiv, 0.4 mmol), adding 1, 4-dioxane (2mL), replacing air in the reactor with argon (1atm), placing the reactor in a 100 ℃ oil bath kettle under the condition of 5W blue light LED illumination, stirring for reaction for 24 hours, detecting the reaction completion by TLC or GC-MS, filtering the reaction mixture by a silica gel short column, washing with ethyl acetate, washing the organic phase with saturated saline water, extracting the aqueous phase with ethyl acetate (3X 10 mL), combining the organic phases, and adding anhydrous Na2SO4Drying, concentrating under reduced pressure to remove solvent to obtain crude product, and purifying by silica gel column chromatography (eluting solvent is n-hexane/ethyl acetate, volume ratio is 10: 1) to obtain 1-benzenesulfonylmethyl-3, 4-dihydronaphthalene shown in formula III-1. The yield is 83%; a yellow oily liquid;1H NMR (400 MHz, CDCl3) δ: 7.81 (d, J = 8.0 Hz, 2H), 7.55 (t, J = 7.2 Hz, 1H), 7.43 (t, J = 7.6 Hz, 2H), 7.13-7.08 (m, 4H), 5.93-5.90 (m, 1H), 4.23 (s, 2H), 2.69 (t, J = 8.0 Hz, 2H), 2.25-2.20 (m, 2H); 13C NMR (100 MHz, CDCl3) δ: 138.3, 135.9, 135.0, 133.6, 128.8, 128.7, 128.7, 127.6, 127.4, 126.4, 125.8, 123.1, 60.0, 27.7, 23.3; HRMS (ESI-TOF) m/z: C17H17O2S (M + H)+ calcd for 285.0944, found 285.0949。
example 2
The alternative photocatalyst is Ir (ppy)3The other reaction conditions and operation were the same as in example 1, and the yield of the objective product was 78%.
Example 3
The photocatalyst was Eosin Y, and the reaction conditions and operation were the same as in example 1, whereby the yield of the objective product was 56%.
Example 4
Replacement of the photocatalyst by Na2Eosin Y, the remaining reaction conditions and operation were the same as in example 1, with a yield of the desired product of 35%.
Example 5
The photocatalyst was not added, and the remaining reaction conditions and operation were the same as in example 1, with a target product yield of 0%.
Example 6
The reaction was carried out in the dark, and the remaining reaction conditions and operation were the same as in example 1, giving a 0% yield of the desired product.
Example 7
Ru(bpy)3Cl2(10 mol%), the rest of the reaction conditions and operation were the same as in example 1, and the yield of the objective product was 85%.
Example 8
Ru(bpy)3Cl2(2 mol%), the rest of the reaction conditions and operation were the same as in example 1, and the yield of the objective product was 68%.
Example 9
The light source was replaced by a 36W fluorescent lamp, the reaction conditions and operation were the same as in example 1, and the yield of the objective product was 33%.
Example 10
The light source was replaced with a 3W blue LED lamp, the remaining reaction conditions and operation were the same as in example 1, and the yield of the target product was 25%.
Example 11
The light source was replaced by a 5W green LED lamp, the remaining reaction conditions and operation were the same as in example 1, and the yield of the objective product was 31%.
Example 12
The alternative base is K2CO3The other reaction conditions and operation were the same as in example 1, and the yield of the objective product was 47%.
Example 13
The alternative base is Na2CO3The other reaction conditions and operation were the same as in example 1, and the yield of the objective product was 63%.
Example 14
The alternative base is Cs2CO3The rest of the reaction conditions and operation were the same as in example 1, and the yield of the objective product was 22%.
Example 15
Pyridine is used as the substitute base, the rest of the reaction conditions and the operation are the same as the example 1, and the yield of the target product is 39%.
Example 16
The substituted base is triethylamine, the rest of the reaction conditions and the operation are the same as the example 1, and the yield of the target product is 26%.
Example 17
The alternative solvent was acetonitrile, the other reaction conditions and operation were the same as in example 1, and the yield of the objective product was 69%.
Example 18
THF was used as an alternative solvent, and the reaction conditions and operation were the same as in example 1, whereby the yield of the objective product was 74%.
Example 19
The solvent was replaced with DMF, and the reaction conditions and operation were the same as in example 1, giving a yield of the desired product of 22%.
Example 20
The alternative solvent was DMSO, the reaction conditions and operation were the same as in example 1, and the yield of the desired product was 29%.
Example 21
The alternative solvent was toluene, the remaining reaction conditions and operation were the same as in example 1, and the yield of the objective product was 41%.
Example 22
The reaction temperature was 110 ℃ and the other reaction conditions and operation were the same as in example 1, giving a yield of the objective product of 71%.
Example 23
The temperature of the substitution reaction was 90 ℃ and the other reaction conditions and operation were the same as in example 1, whereby the yield of the objective product was 66%.
Example 24
The reaction time was 36h, the other reaction conditions and operation were the same as in example 1, and the yield of the objective product was 84%.
From the representative reaction conditions listed in examples 1 to 24, it can be seen from the experimental data that the yield of the objective product is improved slightly when the catalyst charge amount is increased and the reaction time is prolonged, but the inventors have selected the conditions of example 1 as a template and studied the adaptability of reaction substrates of different structures to the reaction conditions of example 1 based on the consideration of the catalyst cost, the reaction efficiency and other factors. See table 1 for results.
Table 1:
Figure 604420DEST_PATH_IMAGE008
Figure 230574DEST_PATH_IMAGE009
Figure 617693DEST_PATH_IMAGE010
Figure 784232DEST_PATH_IMAGE011
Figure 940407DEST_PATH_IMAGE012
Figure 737461DEST_PATH_IMAGE013
Figure 346297DEST_PATH_IMAGE014
wherein the corresponding target product structures (formulas III-2 to III-24) in examples 25 to 47 are as follows:
Figure 519790DEST_PATH_IMAGE015
the embodiments described above are only preferred embodiments of the invention and are not exhaustive of the possible implementations of the invention. Any obvious modifications to the above would be obvious to those of ordinary skill in the art, but would not bring the invention so modified beyond the spirit and scope of the present invention.

Claims (9)

1. A process for preparing a 1-sulfonylmethyl-substituted 3, 4-dihydronaphthalene compound of formula III comprising the steps of:
Figure DEST_PATH_IMAGE002
sequentially adding a vinyl cyclopropane compound shown in a formula I, sulfonyl chloride shown in a formula II, a photocatalyst, alkali and an organic solvent into a Schlenk tube sealing reactor, then protecting the reactor with an inert atmosphere, placing the reactor in an oil bath kettle at 90-110 ℃ under the illumination condition, stirring and reacting for 12-36 h, detecting the reaction completely by TLC and/or GC-MS, and carrying out post-treatment to obtain a target product shown in a formula III;
wherein in formula I and formula III, the structural units
Figure DEST_PATH_IMAGE004
Is represented by C6-C20Aryl of (C)3-C20The heteroaryl group of (a); r1Representing a structural unit
Figure DEST_PATH_IMAGE005
One or more substituents of the above, each R1The substituents are independently of one another selected from hydrogen, C1-C20Alkyl of (C)1-C20Alkoxy group of (C)6-C20Aryl, nitro, halogen, -CN;
in the formulae II and III, R2Is selected from C1-C20Alkyl, substituted or unsubstituted C6-C20Aryl of (C)3-C20The heteroaryl group of (a); and wherein the substituents in said "substituted or unsubstituted" are selected from halogen, C1-C6Alkyl of (C)1-C6Alkoxy group of (C)1-C6Haloalkyl, nitro, C1-C6Acyl of-CN;
and wherein the photocatalyst is selected from Ru (bpy)3Cl2、Ir(ppy)3、Eosin Y、Na2-Eosin Y;
the alkali is selected from 2, 6-dimethylpyridine and K2CO3、Na2CO3、Cs2CO3Any one of pyridine or triethylamine;
the organic solvent is selected from any one of 1, 4-dioxane, THF, DMF, DMSO, toluene and acetonitrile;
the illumination condition is provided by a 5W blue LED lamp, a 3W blue LED lamp, a 36W fluorescent lamp or a 5W green LED lamp.
2. The method of claim 1, wherein: in the formulae I and III, structural units
Figure DEST_PATH_IMAGE006
Is represented by C6-C14Aryl of (C)3-C12The heteroaryl group of (a); r1Representing a structural unit
Figure DEST_PATH_IMAGE007
One or more substituents of the above, each R1The substituents are independently of one another selected from hydrogen, C1-C6Alkyl of (C)1-C6Alkoxy group of (C)6-C14Aryl, nitro, halogen, -CN;
in the formulae II and III, R2Is selected from C2-C12Alkyl, substituted or unsubstituted C6-C14Aryl of (C)3-C12The heteroaryl group of (a); and wherein the substituents in said "substituted or unsubstituted" are selected from halogen, C1-C6Alkyl of (C)1-C6Alkoxy group of (C)1-C6Haloalkyl, nitro, C1-C6Acyl group of-CN.
3. The method of claim 1, wherein: the compound of formula I is selected from compounds having the following structure:
Figure DEST_PATH_IMAGE009
the compound of formula II is selected from compounds having the following structure:
Figure DEST_PATH_IMAGE011
4. a method according to any one of claims 1-3, characterized in that: the photocatalyst is selected from Ru (bpy)3Cl2
The alkali is selected from 2, 6-dimethyl pyridine;
the organic solvent is selected from 1, 4-dioxane;
the illumination condition is provided by a 5W blue LED lamp.
5. A method according to any one of claims 1-3, characterized in that: the inert atmosphere is argon atmosphere or nitrogen atmosphere.
6. A method according to any one of claims 1-3, characterized in that: the reaction time is 24h, and the reaction temperature is 100 ℃.
7. A method according to any one of claims 1-3, characterized in that: the molar ratio of the vinyl cyclopropane compound shown in the formula I, the sulfonyl chloride shown in the formula II, the photocatalyst and the alkali is 1: 1-3: 0.02-0.1: 1-3.
8. The method according to claim 7, wherein the molar ratio of the vinylcyclopropane compound represented by formula I, the sulfonyl chloride compound represented by formula II, the photocatalyst and the base is 1:2:0.05: 2.
9. A method according to any one of claims 1-3, characterized in that: the post-processing comprises the following operations: after the reaction, the reaction solution was filtered through a short column of silica gel, washed with ethyl acetate, the organic phase was washed with saturated brine, the aqueous phase was extracted with ethyl acetate, the organic phases were combined, and anhydrous Na was added2SO4Drying, concentrating under reduced pressure to remove solvent to obtain crude product, separating by silica gel column chromatography with n-hexane/ethyl acetate as eluting solvent, and purifying to obtain target product.
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