CN112409232A - Method for synthesizing asymmetric aryl selenide and aryl tellurium ether based on aryl azo sulfone - Google Patents

Method for synthesizing asymmetric aryl selenide and aryl tellurium ether based on aryl azo sulfone Download PDF

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CN112409232A
CN112409232A CN202011143135.5A CN202011143135A CN112409232A CN 112409232 A CN112409232 A CN 112409232A CN 202011143135 A CN202011143135 A CN 202011143135A CN 112409232 A CN112409232 A CN 112409232A
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aryl
cdcl
nmr
tellurium
selenide
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CN112409232B (en
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芦逵
刘俊杰
赵霞
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Tianjin University of Science and Technology
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C391/00—Compounds containing selenium
    • C07C391/02—Compounds containing selenium having selenium atoms bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C395/00—Compounds containing tellurium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
    • C07D213/61—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic 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
    • C07D333/26—Heterocyclic 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
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

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Abstract

The invention belongs to the field of organic synthesis, and particularly relates to a method for synthesizing asymmetric aryl selenide and aryl tellurium ether by performing cross-coupling reaction on aryl azosulfone and diselenide or ditelluride under the irradiation of visible light. The structural general formula of the compound is shown as the following figure, wherein R1Is halogen, ester group, methyl or methoxy; r2 is aryl; the method is firstly applied to synthesize a series of asymmetric aryl selenide and aryl tellurium ether, and the method is establishedThe synthesis and application of the compound library have wide prospect.

Description

Method for synthesizing asymmetric aryl selenide and aryl tellurium ether based on aryl azo sulfone
Technical Field
The invention relates to the field of organic synthesis, in particular to an organic synthesis method for synthesizing asymmetric aryl selenide and aryl tellurium ether by cross-coupling reaction of aryl azo sulfone and diselenide or ditelluride.
Technical Field
The asymmetric aryl selenide and the aryl tellurium ether are important organic structural units, are widely applied to agriculture, pharmacy and material science, have various biological activities such as oxidation resistance, tumor resistance and the like, and are concerned by organic chemists of various countries in synthesis.
The prior method for synthesizing asymmetric aryl selenide and aryl tellurium ether mainly comprises the step of reacting a series of aromatic substrates such as aryl halides, aryl boric acid and the like with diselenide or ditelluride to obtain the asymmetric aryl selenide and the asymmetric aryl tellurium ether. The above process either requires the use of noble metal silver salts as catalysts or the use of air-sensitive and expensive photosensitizers. This leaves a wide space for the subsequent development of new methods for synthesizing such compounds.
Disclosure of Invention
The purpose of the invention is:
under the induction of visible light, aryl azo sulfone derivative and diselenide or ditelluride are reacted directly to synthesize asymmetrical aryl selenide and aryl telluride.
The purpose of the invention is realized by the following technical scheme:
Figure RE-GSB0000191258720000011
the nomenclature and structures of the synthesized asymmetric arylselenoethers and aryltelluroethers are shown in the following table:
TABLE 1 nomenclature and Structure of asymmetric arylselenoethers and aryltelluroethers
Figure RE-GSB0000191258720000012
Figure RE-GSB0000191258720000021
Figure RE-GSB0000191258720000031
The invention has the advantages and positive effects that:
1. the raw materials are cheap and easy to obtain.
2. The use of metal catalysts and photosensitizers is not required.
3. The method is simultaneously suitable for preparing the asymmetric aryl selenide and the asymmetric aryl tellurium ether.
Detailed Description
For understanding the present invention, the present invention will be further described with reference to the following examples: the following examples are illustrative and not intended to be limiting, and are not intended to limit the scope of the invention.
The structural formula of the asymmetric aryl selenide and the aryl tellurium ether is shown as the following formula:
Figure RE-GSB0000191258720000041
the specific nomenclature and structure are shown in table 1 above.
The asymmetric aryl selenide and the aryl tellurium ether are synthesized by the following general synthesis method:
adding aryl azo sulfone derivative (0.3mmol), diselenide or ditelluril (0.36mmol) and acetonitrile (3mL) into a 10mL branch pipe in sequence, then reacting under the irradiation of a 21W blue LED lamp, detecting the reaction by a dot plate after 21-24h, taking petroleum ether and ethyl acetate as mobile phases, wherein the ratio of petroleum ether to ethyl acetate is 15: 1-30: 1, and carrying out column chromatography to obtain the compounds shown in the table 1, wherein the yield is 38-91%.
The following examples are intended to illustrate the present invention.
Example 1
(the structure is shown in the following formula).
Figure RE-GSB0000191258720000042
The synthesis method of example 1 is the same as the above synthesis method.
Yellow oil; yield: 91 percent.
1H NMR(400MHz，CDCl3)：δ7.88(d，J＝8.4Hz，2H)，7.58-7.56(m，2H)，7.39-7.32(m，5H)，4.35(q，J ＝7.2Hz，2H)，1.37(t，J＝7.2Hz，3H).13C NMR(100MHz，CDCl3)：δ166.3，139.3，134.8，130.5，130.1， 129.6，128.9，128.7，128.4，60.9，14.3.
Example 2
(the structure is shown in the following formula).
Figure RE-GSB0000191258720000043
The synthesis method of example 2 is the same as the general synthesis method described above.
Yellow oil; yield: 78 percent.
1H NMR(400MHz，CDCl3)：δ7.60-7.58(m，2H)，7.35-7.32(m，3H)，7.21-7.16(m，1H)，6.95(dd，J＝ 7.8，1.6Hz，1H)，6.85(d，J＝8.2Hz，1H)，6.81-6.77(m，1H)，3.88(s，3H).13C NMR(100MHz，CDCl3)：δ156.5，135.4，130.7，129.4，128.2，128.1，127.6，121.8，121.6，110.3，55.8.
Example 3
(the structure is shown in the following formula).
Figure RE-GSB0000191258720000051
The synthesis method of example 3 is the same as the general synthesis method described above.
Yellow oil; yield: 91 percent.
1H NMR(400MHz，CDCl3)：δ7.53-7.49(m，3H)，7.34-7.29(m，4H)，7.22(d，J＝8.4Hz，1H).13C NMR (100MHz，CDCl3)：δ133.9，133.3，133.1，131.5，131.3，131.2，130.8，129.6，129.4，128.2.
Example 4
(the structure is shown in the following formula).
Figure RE-GSB0000191258720000052
The synthesis method of example 4 is the same as the above synthesis method.
A white solid; yield: 56 percent.
1H NMR(400MHz，CDCl3)：δ7.43(d，J＝7.6Hz，2H)，7.27-7.26(m，3H)，6.45(s，2H)，3.84(s，3H)， 3.79(s，6H).13C NMR(100MHz，CDCl3)：δ153.5，137.8，135.5，131.9，129.2，127.0，124.3，111.0， 60.8，56.1.HRMS(ESI)m/z calcd for C15H17O3Se[M+H]+325.0337；found 325.0340.
Example 5
(the structure is shown in the following formula).
Figure RE-GSB0000191258720000053
The synthesis method of example 5 is the same as the general synthesis method described above.
A yellow solid; yield: and 55 percent.
1H NMR(400MHz，CDCl3)：δ7.99(s，1H)，7.81-7.89(m，1H)，7.73(d，J＝8.0Hz，2H)，7.50-7.46(m， 4H)7.28-7.27(m，3H).13C NMR(100MHz，CDCl3)：δ134.0，132.9，132.4，132.0，131.2，130.4，129.3， 128.8，128.4，127.7，127.4，127.3，126.5，126.2.
Example 6
(the structure is shown in the following formula).
Figure RE-GSB0000191258720000061
The synthesis method of example 6 is the same as the general synthesis method described above.
Yellow oil; yield: 86 percent.
1H NMR(400MHz，CDCl3)：δ7.92(d，J＝8.0Hz，2H)，7.68(t，J＝1.8Hz，1H)，7.47-7.41(m，4H)，7.19 (t，J＝8.0Hz，1H)，4.36(q，J＝7.2Hz，2H)，1.38(t，J＝7.2Hz，3H).13C NMR(100MHz，CDCl3)：δ 166.0，137.7，136.4，132.5，131.3，131.2，130.8，130.3，129.2，123.2，61.0，14.3.HRM5(ESI)m/z calcd for C15H14BrO2Se[M+H]+384.9337；found 384.9340.
Example 7
(the structure is shown in the following formula).
Figure RE-GSB0000191258720000062
The synthesis method of example 7 is the same as the general synthesis method described above.
Yellow oil; yield: 82 percent.
1H NMR(400MHz，CDCl3)：δ7.53(d，J＝8.0Hz，2H)，7.41(t，J＝1.8Hz，1H)，7.29(d，J＝8.0Hz，1H)， 7.20(d，J＝8.0Hz，1H)，7.07(t，J＝8.0Hz，1H)，6.89(d，J＝8.0Hz，2H)，3.83(s，3H).13C NMR(100 MHz，CDCl3)：δ160.1，137.1，135.7，132.6，130.2，129.2，128.7，123.1，118.7，115.3，55.2.
Example 8
(the structure is shown in the following formula).
Figure RE-GSB0000191258720000063
The synthesis method of example 8 is the same as the general synthesis method described above.
Yellow oil; yield: 38 percent.
1H NMR(400MHz，CDCl3)：δ7.98-7.84(m，2H)，7.58-7.49(m，6H)，4.37(q，J＝6.8Hz，2H)，1.39(t，J ＝6.8Hz，3H).19F NMR(376MHz，CDCl3)：δ-62.73，(s，3F).13C NMR(100MHz，CDCl3)：δ166.0， 136.5，135.4，133.0，132.5，130.5，130.2(q，J＝15.3Hz，1C)，129.8，126.2(q，J＝3.7Hz，1C)，123.9(q， J＝271.3Hz，1C)，61.1，14.3.
Example 9
(the structure is shown in the following formula).
Figure RE-GSB0000191258720000071
The synthesis of example 9 was performed as described above.
Yellow oil; yield: 70 percent.
1H NMR(400MHz，CDCl3)：δ7.88(d，J＝8.4Hz，2H)，7.39(d，J＝8.4Hz，2H)，7.24(t，J＝7.8Hz，1H)， 7.14-7.12(m，1H)，7.11-7.10(m，1H)，6.90-6.87(m，1H)，4.35(q，J＝7.2Hz，2H)，3.77(s，3H)，1.37(t， J＝7.2Hz，3H).13C NMR(100MHz，CDCl3)：δ166.2，139.1，130.6，130.1，129.7，128.6，126.8，119.7， 114.3，60.9，55.3，14.2.HRMS(ESI)m/z calcd for C16H17O3Se[M+H]+337.0337；found 337.0333.
Example 10
(the structure is shown in the following formula).
Figure RE-GSB0000191258720000072
The synthesis method of example 10 is the same as the above synthesis method.
Yellow oil; yield: 53 percent.
1H NMR(400MHz，CDCl3)：δ7.48(d，J＝8.8Hz，2H)，7.18(d，J＝7.2Hz，1H)，7.14-7.08(m，2H)， 7.04-7.00(m，1H)，6.88(d，J＝8.8Hz，2H)，3.83(s，3H)，2.40(s，3H).13C NMR(100MHz，CDCl3)：δ 159.7，137.8，136.6，133.9，130.7，130.0，126.5，126.5，119.2，115.2，55.2，21.8.
Example 11
(the structure is shown in the following formula).
Figure RE-GSB0000191258720000073
The synthesis of example 11 was performed as described above.
A yellow solid; yield: 87 percent.
1H NMR 400MHz，CDCl3)：δ7.77(d，J＝2.0Hz，1H)，7.59-7.56(m，2H)，7.44-7.42(m，1H)，7.41-7.35 (m，4H).13C NMR(100MHz，CDCl3)：δ148.1，135.2，134.9，133.2，132.1，130.0，129.1，127.9，127.2， 124.9.HRMS(ESI)m/z calcd for C12H9CINO2Se[M+H]+313.9482；found 313.9487.
Example 12
(the structure is shown in the following formula).
Figure RE-GSB0000191258720000081
The synthesis method of example 12 is the same as the general synthesis method described above.
Yellow oil; yield: 75 percent.
1H NMR(400MHz，CDCl3)：δ7.88(d，J＝8.5Hz，2H)，7.59-7.56(m，2H)，7.39-7.32(m，5H)，4.35(q，J ＝7.2Hz，2H)，1.37(t，J＝7.2Hz，3H).13C NMR(100MHz，CDCl3)：δ166.2，139.4，134.8，130.4，130.1， 129.6，128.8，128.6，128.4，60.9，14.3.
Example 13
(the structure is shown in the following formula).
Figure RE-GSB0000191258720000082
The synthesis method of example 13 is the same as the general synthesis method described above.
Yellow oil; yield: 57 percent.
1H NMR(400MHz，CDCl3)：δ7.60-7.57(m，2H)，7.48-7.43(m，4H)，7.39-7.33(m，3H).19F NMR(376 MHz，CDCl3)：δ-62.78，(s，3F).13C NMR(100MHz，CDCl3)：δ164.0，152.3，145.1，132.0，130.2，(d，J＝ 191.7Hz，1C)，130.3(q，J＝235.8Hz，1C)，126.9，117.8，112.1，53.5(q，J＝5.1Hz，1C).
Example 14
(the structure is shown in the following formula).
Figure RE-GSB0000191258720000083
The synthesis method of example 14 is the same as the above synthesis method.
Yellow oil; yield: and 47 percent.
1H NMR(400MHz，CDCl3)：δ7.74(d，J＝7.4Hz，2H)，7.58-7.56(m，2H)，7.24-7.16(m，3H)，6.80(d，J ＝8.8Hz，2H)，3.81(s，3H).13C NMR(100MHz，CDCl3)：δ160.0，141.2，136.4，129.3，127.2，115.9， 115.5，103.2，55.2.
Example 15
(the structure is shown in the following formula).
Figure RE-GSB0000191258720000091
The synthesis of example 15 was performed as described above.
Yellow oil; yield: 48 percent.
1H NMR(400MHz，CDCl3)：δ8.92(d，J＝2.0Hz，1H)，8.25(d，J＝2.0Hz，1H)，8.08(d，J＝8.8Hz，1H)， 7.72-7.68(m，2H)，7.56-7.54(m，1H)，7.53-7.49(m，2H)，7.32-7.28(m，.3H).13C NMR(100MHz， CDCl3)：δ148.9，142.5，141.7，134.3，131.9，130.1，129.1，128.9，128.9，127.9，127.4，126.7，125.8. HRMS(ESl)m/z calcd for C15H12NTe[M+H]+336.0026；found 336.0030.
Example 16
(the structure is shown in the following formula).
Figure RE-GSB0000191258720000092
The synthesis method of example 16 is the same as the general synthesis method described above.
Yellow oil; yield: 77 percent.
1H NMR(400MHz，CDCl3)：δ8.36(d，J＝2.2Hz，1H)，7.72(dd，J＝8.4，2.2Hz，1H)，7.35-7.33(m，2H)， 7.25-7.19(m，3H)，6.70(d，J＝8.4Hz，1H)，3.93(s，3H).13C NMR(100MHz，CDCl3)：δ164.0，152.2， 145.2，132.0，131.2，129.3，126.9，117.9，112.3，53.7.
Example 17
(the structure is shown in the following formula).
Figure RE-GSB0000191258720000093
The synthesis of example 17 was performed as described above.
Yellow oil; yield: 78 percent.
1H NMR(400MHz，CDCl3)：δ8.41(d，J＝2.4Hz，1H)，7.65(dd，J＝6.8，2.4Hz，1H)，7.50-7.47(m，2H)， 7.33-7.28(m，3H)，7.20(dd，J＝8.2，0.4Hz，1H).13C NMR(100MHz，CDCl3)：δ152.2，150.3，142.5， 133.6，129.7，129.0128.2，127.6，124.9.HRMS(ESl)m/z calcd for C11H8CINTeNa[M+Na]+341.9300； found 341.9301.
Example 18
(the structure is shown in the following formula).
Figure RE-GSB0000191258720000101
The synthesis of example 18 was performed as described above.
A yellow solid; yield: and 47 percent.
1H NMR(400MHz，CDCl3)：δ8.89(s，1H)，8.64(d，J＝1.8Hz，1H)，8.56(dd，J＝1.2，4.8Hz，1H)，8.01 (dt，J＝7.8，1.8Hz，1H)7.92(dd，J＝2.2，7.2Hz，1H)7.22-7.19(m，2H).13C NMR(100MHz，CDCl3)：δ 157.4，157.3，151.9，149.3，147.4，145.7，125.7，125.0，111.1，109.2.HRMS(ESI)m/z calcd for C10H8CIN2Te[M+H]+320.9433；found 320.9435.
Example 19
(the structure is shown in the following formula).
Figure RE-GSB0000191258720000102
The synthesis method of example 19 is the same as the above synthesis method.
Yellow oil; yield: 53 percent.
1H NMR(400MHz，CDCl3)：δ7.74-7.72(m，2H)，7.46-7.37(m，3H)，7.30(d，J＝5.2Hz，1H)，6.35(d，J ＝5.2Hz，1H)，3.92(s，3H).13C NMR(100MHz，CDCl3)：δ163.0，140.5，136.8，131.0，129.6，129.3， 129.2，128.3，122.4，52.1.HRMS(ESl)m/z calcd for C12H10O2STeNa[M+Na]+370.9356；found 370.9356.

Claims (4)

1. The structural formula of the asymmetric aryl selenide and aryl tellurium ether is shown as the following figure:
Figure FSA0000222498290000011
2. the novel class of asymmetric arylselenoethers and aryltellurils of claim 1 wherein: said R1Is halogen, ester group, methyl or methoxy.
3. The novel class of asymmetric arylselenoethers and aryltellurils of claim 1 wherein: said R2Is an aryl group.
4. The novel asymmetric arylselenoethers and aryltellurils of claim 1, which are prepared by the following synthetic routes:
Figure FSA0000222498290000012
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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107188840A (en) * 2017-05-16 2017-09-22 温州医科大学 A kind of synthetic method of asymmetric diaryl selenide compound
CN107188841A (en) * 2017-05-16 2017-09-22 温州医科大学 A kind of synthetic method of asymmetric diaryl list selenide compound

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CN107188840A (en) * 2017-05-16 2017-09-22 温州医科大学 A kind of synthetic method of asymmetric diaryl selenide compound
CN107188841A (en) * 2017-05-16 2017-09-22 温州医科大学 A kind of synthetic method of asymmetric diaryl list selenide compound

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