CN104803948A - Preparation method for 2-amino benzo phenoselenazine derivative - Google Patents

Preparation method for 2-amino benzo phenoselenazine derivative Download PDF

Info

Publication number
CN104803948A
CN104803948A CN201510249209.6A CN201510249209A CN104803948A CN 104803948 A CN104803948 A CN 104803948A CN 201510249209 A CN201510249209 A CN 201510249209A CN 104803948 A CN104803948 A CN 104803948A
Authority
CN
China
Prior art keywords
preparation
selenium
isocyano
aryl
amino benzo
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CN201510249209.6A
Other languages
Chinese (zh)
Other versions
CN104803948B (en
Inventor
纪顺俊
汪顺义
方毅
申晓斌
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Suzhou University
Original Assignee
Suzhou University
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Suzhou University filed Critical Suzhou University
Priority to CN201510249209.6A priority Critical patent/CN104803948B/en
Publication of CN104803948A publication Critical patent/CN104803948A/en
Application granted granted Critical
Publication of CN104803948B publication Critical patent/CN104803948B/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D293/00—Heterocyclic compounds containing rings having nitrogen and selenium or nitrogen and tellurium, with or without oxygen or sulfur atoms, as the ring hetero atoms
    • C07D293/10—Heterocyclic compounds containing rings having nitrogen and selenium or nitrogen and tellurium, with or without oxygen or sulfur atoms, as the ring hetero atoms condensed with carbocyclic rings or ring systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

The invention relates to a preparation method for a 2-amino benzophenoselenazine derivative. According to the preparation method, the 2-amino benzophenoselenazine derivative is prepared by taking ortho-functionalized aryl isonitrile, selenium powder and secondary amine as raw materials and reacting at room temperature and under an alkaline condition of triethylamine. Compared with the prior art, the preparation method disclosed by the invention is easily available in raw materials, mild in reaction conditions, environment-friendly, free of any catalyst and inert gas protection, simple and convenient to operate and relatively high in yield, and lays a foundation for industrial production; the reaction conditions are applicable to amplification reaction.

Description

The preparation method of 2-amino benzo selenium oxazine derivative
Technical field
The invention belongs to organic compound field, be specifically related to the preparation method of a kind of 2-amino benzo selenium oxazine derivative.
Background technology
Organic selenium compounds is the special organic compound of a class, achieves in recent years develop rapidly its research, make its in every respect have very important application, especially at organic synthesis and field of medicaments.
In organic synthesis field, disclosed in following document, organic selenium compounds can be used for asymmetric catalysis, free radical reaction etc.[S.A.Shahzad,T.Wirth,Angew.Chem.Int.Ed.2009,48,2588-2591]，[D.M.Freudendahl,S.Santoro,S.A.Shahzad,C.Santi,T.Wirth,Angew.Chem.Int.Ed.2009,48,8409-8411]，[J.Trenner,C.Depken,T.Weber,A.Breder,Angew.Chem.Int.Ed.2013,52,8952-8956]。
At field of medicaments, outstanding biology and the medicinal activities such as existing bibliographical information organic selenium compounds also shows anticancer, antibacterial.[G.Mugesh,W.W.du Mont,H.Sies,Chem.Rev.2001,101,2125],[C.W.Nogueira,G.Zeni,J.B.T.Rocha,Chem.Rev.2004,104,6255]。
Different selenourea skeleton is extensively present in natural product and drug molecule, and wherein representative structural formula is as follows:
Shin-ike seminar reports by amido lithium, selenium powder and isonitrile three components are obtained by reacting the different selenourea intermediate of lithiumation, then with butyl iodide, substituted alkylated reaction occur, and obtain different selenourea derivative [H.Maeda with the productive rate of 34%-86%, T.Matsuya, N.Kambe, N.Sonoda, S.Fujiwara, T.Shin-ike, Tetrahedron.1997,53,12159].Minoura seminar reports by adjacent amino-benzene acetylene-derivative and isoselenocyanates under condition of no solvent, carry out microwave radiation heating is reacted, 1 can be obtained with the productive rate of 51%-88%, 3-benzo selenium oxazine derivative [H.Sashida, C.Pana, M.Kanamea, M.Minoura, Synthesis.2010,18,3091-3096].
In preparation method disclosed in above-mentioned document, need to use the reagent that Lithamide is not easy to operation, or isoselenocyanates toxic reagent, and productive rate is medium on the upper side, is not suitable for iodine.Therefore, easy to use be easy to get raw material, with the method high yield of easy gentleness synthesis obtain benzo selenium oxazine derivative, organic chemistry and pharmaceutical chemical field all significant.
Summary of the invention
In view of this, the object of the invention is to solve the problems of the technologies described above, providing the preparation method of 2-amino benzo selenium oxazine derivative, preparation-obtained 2-amino benzo selenium oxazine derivative can be used for organic synthesis and biomedicine field.Technical solution of the present invention is as follows:
The preparation method of 2-of the present invention amino benzo selenium oxazine derivative, with ortho position functionalization aryl isonitrile, selenium powder and secondary amine for raw material, the obtained 2-of reaction amino benzo selenium oxazine derivative under room temperature, triethylamine alkaline condition, wherein, the mol ratio of ortho position functionalization aryl isonitrile, selenium powder and secondary amine is 1 ︰ 1.2 ~ 1.8 ︰ 1.2 ~ 1.8.
Further, described ortho position functionalization aryl isonitrile is following structure in the present invention
Wherein, R 1substituting group is alkyl, aryl, halogen, amido or-oxyl; R 2substituting group is alkyl, aryl or alkoxyl group, and C substituting group is H, alkyl, aryl or alkoxyl group.
The present invention further, described ortho position functionalization aryl isonitrile comprises 2-isocyano-methyl cinnamate, 2-isocyano-ethyl cinnamate, 4-chloro-2-isocyano-methyl cinnamate, 5-fluoro-2-isocyano-methyl cinnamate, 5-trifluoromethyl-2-isocyano-methyl cinnamate, 5-methyl-2-isocyano-methyl cinnamate or 3-(2-isocyanatophenyl)-1-phenyl third-2-alkene-1-ketone.
Further, described secondary amine comprises piperidines, diethylamine or N-methylbenzylamine in the present invention.
Further, the mol ratio of described triethylamine and described ortho position functionalization aryl isonitrile is 1.5 ︰ 1 in the present invention.
The present invention further, with 1,2-ethylene dichloride as reaction solvent.
Compared with prior art, the present invention has following beneficial effect:
1. the inventive method raw material is simple and easy to get, and reaction conditions is gentle, and environmental friendliness, without the need to any catalyzer and protection of inert gas;
2. the inventive method simple operating steps, productive rate is higher, and its reaction conditions is applicable to iodine, for industrial production is laid a good foundation.
Above-mentioned explanation is only the general introduction of technical solution of the present invention, in order to better understand technique means of the present invention, and can be implemented according to the content of specification sheets, be described in detail as follows below with preferred embodiment of the present invention.The specific embodiment of the present invention is provided in detail by following examples.
Embodiment
The embodiment of the invention discloses the preparation method of 2-amino benzo selenium oxazine derivative.Those skilled in the art can use for reference present disclosure, and suitable improving technique parameter realizes.Special needs to be pointed out is, all similar replacements and change apparent to those skilled in the art, they are all deemed to be included in the present invention.Application of the present invention is described by preferred embodiment, related personnel obviously can not depart from content of the present invention, spirit and scope application as herein described is changed or suitably change with combination, realize and apply the technology of the present invention.
The preparation method of 2-of the present invention amino benzo selenium oxazine derivative, with ortho position functionalization aryl isonitrile, selenium powder and secondary amine for raw material, the obtained 2-of reaction amino benzo selenium oxazine derivative under room temperature, triethylamine alkaline condition, wherein, the mol ratio of ortho position functionalization aryl isonitrile, selenium powder and secondary amine is 1 ︰ 1.2 ~ 1.8 ︰ 1.2 ~ 1.8, preferably, the mol ratio of ortho position functionalization aryl isonitrile, selenium powder and secondary amine is specially 1 ︰ 1.5 ︰ 1.5.
As the ortho position functionalization aryl isonitrile of the specific embodiment of the invention, ortho position functionalization aryl isonitrile is following structure
R 1substituting group is alkyl, aryl, halogen, amido or-oxyl; R 2substituting group is alkyl, aryl or alkoxyl group, and C substituting group is H, alkyl, aryl or alkoxyl group, and when C is alkyl, C substituting group can become ring with N, and the substituent number of C meets the requirement of atom N polarity formula rock steady structure.
Particularly, reaction raw materials ortho position of the present invention functionalization aryl isonitrile includes but not limited to:
2-isocyano-methyl cinnamate;
2-isocyano-ethyl cinnamate;
4-chloro-2-isocyano-methyl cinnamate;
5-fluoro-2-isocyano-methyl cinnamate;
5-trifluoromethyl-2-isocyano-methyl cinnamate;
5-methyl-2-isocyano-methyl cinnamate or 3-(2-isocyanatophenyl)-1-phenyl third-2-alkene-1-ketone.
As the reaction raw materials in the specific embodiment of the invention, said second amine includes but not limited to piperidines, diethylamine or N-methylbenzylamine.Reaction system with 1,2-ethylene dichloride as reaction solvent, but can be not limited thereto a kind of solvent, and the method that all conventional techniques means are replaced is all in scope.
For lab scale reaction, the overall method steps of the present invention is as follows:
Step one, in 10mL round-bottomed flask, add aforementioned ortho position functionalization aryl isonitrile 0.3mmol, selenium powder 0.45mmol, secondary amine 0.45mmol and triethylamine 0.45mmol and 1,2-ethylene dichloride 2mL, at room temperature stir, TLC detection reaction is complete.
Step 2, after reaction terminates, removal of solvent under reduced pressure, obtains the amino benzo selenium of the 2-after purifying oxazine derivative with ethyl acetate, sherwood oil for eluent column chromatography.
In order to understand the present invention further, below in conjunction with embodiment, the present invention is described in detail.
The preparation of [embodiment 1] 2-(2-(piperidino)-4H-benzo [d] [1,3]-4-selenium piperazine) methyl acetate
1, in 10mL round-bottomed flask, add 2-isonitrile base methyl cinnamate (0.3mmol), selenium powder (0.45mmol), piperidines (0.45mmol) and triethylamine (0.45mmol) and 1,2-ethylene dichloride 2mL, at room temperature stir, TLC detection reaction is complete.
2, after reaction terminates, removal of solvent under reduced pressure, with ethyl acetate, sherwood oil for eluent column chromatography, obtains 2-(2-(piperidino)-4H-benzo [d] [1,3]-4-selenium piperazine) methyl acetate pale yellow oily liquid body.Productive rate: 90%.
Infrared spectra (neat, ν, cm-1): 2933,2851,1736,1602,1550,1257,1224,1122,758.
Proton nmr spectra (CDCl3,400MHz) (δ, ppm): 7.24 – 7.16 (m, 1H, Ar-H), 7.11 (dd, J=10.8,8.5Hz, 2H, Ar-H), 6.98 (t, J=7.4Hz, 1H, Ar-H), 4.51 (dd, J=8.5,7.0Hz, 1H, CH), 3.78 – 3.68 (m, 4H, CH2), 3.64 (s, 3H, CH3), 2.92 – 2.79 (m, 2H, CH2), 1.63 (ddt, J=26.7,10.6,5.2Hz, 6H, CH2).
Carbon-13 nmr spectra (CDCl3,100MHz) (δ, ppm): 171.20,150.82,146.83,128.18,125.67,125.49,122.99,122.00,51.63,48.68,41.91,35.59,25.96,25.08.
High resolution mass spec (ESI): m/z calcd for:353.0763 [M+H]+, found:353.0765.
The preparation of [embodiment 2] 2-(the fluoro-4H-benzo [d] [1,3] of 2-(diethylin)-6--4-selenium piperazine) methyl acetate
1, in 10mL round-bottomed flask, add 5-fluoro-2-isocyano-methyl cinnamate (0.3mmol), selenium powder (0.45mmol), diethylamine (0.45mmol) and triethylamine (0.45mmol) and 1,2-ethylene dichloride 2mL, at room temperature stir, TLC detection reaction is complete.
2, after reaction terminates, removal of solvent under reduced pressure, 2-(the fluoro-4H-benzo [d] [1,3] of 2-(diethylin)-6--4-selenium piperazine) the orange-yellow oily liquids of methyl acetate is obtained, productive rate: 94% for eluent column chromatography with ethyl acetate, sherwood oil.
Infrared spectra (neat, ν, cm-1): 2971,2932,2871,1736,1611,1559,1484,1230,1117,862,821,766.
Proton nmr spectra (CDCl36,400MHz) (δ, ppm): 7.03 (dd, J=8.6,5.5Hz, 1H, Ar-H), 6.89 (ddd, J=17.2,8.6,2.9Hz, 2H, Ar-H), 4.43 (dd, J=8.5,7.0Hz, 1H, CH), 3.67 (s, 3H, CH3), 3.59 (dq, J=24.4,7.1Hz, 4H, CH2), 2.89 – 2.77 (m, 2H, CH2), 1.20 (t, J=7.1Hz, 6H, CH3).
Carbon-13 nmr spectra (CDCl3,100MHz) (δ, ppm): 171.19,159.64,157.23,149.24,126.73,126.66,123.27,115.09,114.88,112.37,112.14,51.86,44.38,41.51,35.25,14.33.
High resolution mass spec (ESI): m/z calcd for:358.0669 [M+H]+, found:359.0675.
The preparation of [embodiment 3] 2-(2-(diethylin)-6-trifluoromethyl-4H-benzo [d] [1,3]-4-selenium piperazine) methyl acetate
1, in 10mL round-bottomed flask, add 5-trifluoromethyl-2-isocyano-methyl cinnamate (0.3mmol), selenium powder (0.45mmol), diethylamine (0.45mmol) and triethylamine (0.45mmol) and 1,2-ethylene dichloride 2mL, at room temperature stir, TLC detection reaction is complete.
2, after reaction terminates, removal of solvent under reduced pressure, obtains 2-(2-(diethylin)-6-trifluoromethyl-4H-benzo [d] [1,3]-4-selenium piperazine) methyl acetate faint yellow solid with ethyl acetate, sherwood oil for eluent column chromatography.Productive rate 80%, fusing point: 49.5-50.3 DEG C.
Infrared spectra (neat, ν, cm-1): 2971,2933,1741,1533,1327,1301,1231,1163,1101,1067,836.
Proton nmr spectra (CDCl3,400MHz) (δ, ppm): 7.43 (dd, J=10.3,2.2Hz, 2H, Ar-H), 7.15 (d, J=8.2Hz, 1H, Ar-H), 4.58 – 4.47 (m, 1H, CH), 3.67 (s, 3H, CH3), 3.58 (dq, J=13.8,6.8Hz, 4H, CH2), 2.90 – 2.79 (m, 2H, CH2), 1.23 (t, J=7.1Hz, 6H, CH3).
Carbon-13 nmr spectra (CDCl3,100MHz) (δ, ppm): 171.06,151.20,150.31,125.72,125.26,125.22,124.20,123.88,123.18,123.15,122.13,51.92,44.71,41.69,35.29,14.32.
High resolution mass spec (ESI): m/z calcd for:409.0637 [M+H]+, found:409.0646.
The preparation of [embodiment 4] 2-(2-(diethylin)-4H-benzo [d] [1,3]-4-selenium piperazine) methyl acetate
1, in 10mL round-bottomed flask, add 2-isocyano-methyl cinnamate (0.3mmol), selenium powder (0.45mmol), diethylamine (0.45mmol) and triethylamine (0.45mmol) and 1,2-ethylene dichloride 2mL, at room temperature stir, TLC detection reaction is complete.
2, after reaction terminates, removal of solvent under reduced pressure, 2-(2-(diethylin)-4H-benzo [d] [1,3]-4-selenium piperazine) methyl acetate pale yellow oily liquid body is obtained, productive rate: 98% for eluent column chromatography with ethyl acetate, sherwood oil.
Infrared spectra (neat, ν, cm-1): 3061,3028,2978,2904,1730,1603,1546,1411,1372,1189,759,697.
Proton nmr spectra (CDCl3,400MHz) (δ, ppm): 7.26 – 7.07 (m, 3H, Ar-H), 6.98 (td, J=7.3,1.4Hz, 1H, Ar-H), 4.51 (dd, J=8.7,6.9Hz, 1H, CH), 3.73 – 3.52 (m, 7H, CH3, CH2), 2.93 – 2.79 (m, 2H, CH2), 1.22 (t, J=7.1Hz, 6H, CH3).
Carbon-13 nmr spectra (CDCl3,100MHz) (δ, ppm): 171.43,149.56,147.19,128.32,125.75,125.52,122.73,122.04,51.76,44.35,41.85,35.69,14.33.
High resolution mass spec (ESI): m/z calcd for:341.0763 [M+H]+, found:341.0765.
The preparation of [embodiment 5] 2-(2-(benzyl (methyl) amido)-4H-benzo [d] [1,3]-4-selenium piperazine) ethyl acetate
1, in 10mL round-bottomed flask, add 2-isocyano-ethyl cinnamate (0.3mmol), selenium powder (0.45mmol), N-methylbenzylamine (0.45mmol) and triethylamine (0.45mmol) and 1,2-ethylene dichloride 2mL, at room temperature stir, at room temperature stir, TLC detection reaction is complete.
2, after reaction terminates, removal of solvent under reduced pressure, pale yellow oily liquid body 2-(2-(benzyl (methyl) amido)-4H-benzo [d] [1,3]-4-selenium piperazine) ethyl acetate is obtained for eluent column chromatography with ethyl acetate, sherwood oil.Productive rate: 98%.
Infrared spectra (neat, ν, cm-1): 3061,3028,2978,2904,1730,1603,1546,1478,1372,1189,759,732,697.
Proton nmr spectra (CDCl3,400MHz) (δ, ppm): 7.39 – 7.26 (m, 5H, Ar-H), 7.26 – 7.16 (m, 3H, Ar-H), 7.03 (td, J=7.3,1.4Hz, 1H, Ar-H), 4.86 (s, 2H, CH2), 4.63 – 4.51 (m, 1H, CH), 4.14 (q, J=7.1Hz, 2H, CH2), 3.19 (s, 3H, CH3), 2.96 – 2.85 (m, 2H, CH2), 1.23 (t, J=7.1Hz, 3H, CH3).
Carbon-13 nmr spectra (CDCl3,100MHz) (δ, ppm): 170.86,146.99,137.62,128.68,128.39,127.38,125.89,125.74,123.21,122.00,60.74,55.00,42.26,37.02,36.15,14.27.
High resolution mass spec (ESI): m/z calcd for:403.0919 [M+H]+, found:403.0929.
The preparation of [embodiment 6] 2-(2-(diethylin)-4H-benzo [d] [1,3]-4-selenium piperazine)-1-phenylethyl-1-ketone
1, in 10mL round-bottomed flask, add 3-(2-isocyanatophenyl)-1-phenyl third-2-alkene-1-ketone (0.3mmol), selenium powder (0.45mmol), diethylamine (0.45mmol) and triethylamine (0.45mmol) and 1,2-ethylene dichloride 2mL, at room temperature stir, at room temperature stir, TLC detection reaction is complete.
2, after reaction terminates, removal of solvent under reduced pressure, obtains orange oily liquids 2-(2-(diethylin)-4H-benzo [d] [1,3]-4-selenium piperazine)-1-phenylethyl-1-ketone with ethyl acetate, sherwood oil for eluent column chromatography.Productive rate 94%.
Infrared spectra (neat, ν, cm-1): 2969,2929,1682,1599,1547,1357,1231,1116,756,689.
Proton nmr spectra (CDCl3, 400MHz) (δ, ppm): δ 7.91 – 7.84 (m, 2H, Ar-H), 7.54 (t, J=7.4Hz, 1H, Ar-H), 7.42 (t, J=7.6Hz, 2H, Ar-H), 7.25 – 7.14 (m, 3H, Ar-H), 6.99 (td, J=7.4, 1.5Hz, 1H, Ar-H), 4.78 (dd, J=9.4, 5.1Hz, 1H, CH), 3.68 (tt, J=14.2, 8.3Hz, 3H, CH3), 3.52 (dq, J=14.1, 7.0Hz, 2H, CH2), 3.37 (dd, J=17.3, 5.1Hz, 1H, CH), 1.19 (t, J=7.1Hz, 6H, CH3).
Carbon-13 nmr spectra (CDCl3,100MHz) (δ, ppm): δ 197.67,150.50,147.43,136.93,133.29,128.61,128.20,128.14,125.85,125.50,122.87,122.67,45.12,44.16,34.95,14.36.
High resolution mass spec (ESI): m/z calcd for:387.0970 [M+H]+, found:387.0983.
The amplification preparation of [embodiment 7] 2-(2-(diethylin)-4H-benzo [d] [1,3]-4-selenium piperazine) methyl acetate
1, in 10mL round-bottomed flask, add 2-isocyano-methyl cinnamate (5mmol), selenium powder (7.5mmol), diethylamine (7.5mmol) and triethylamine (7.5mmol) and 1,2-ethylene dichloride 15mL, at room temperature stir, TLC detection reaction is complete.
2, after reaction terminates, removal of solvent under reduced pressure, 2-(2-(diethylin)-4H-benzo [d] [1,3]-4-selenium piperazine) methyl acetate pale yellow oily liquid body is obtained, productive rate: 90% for eluent column chromatography with ethyl acetate, sherwood oil.

Claims (6)

  1. The preparation method of 1.2-amino benzo selenium oxazine derivative, its feature exists:
    With ortho position functionalization aryl isonitrile, selenium powder and secondary amine for raw material, the obtained 2-of reaction amino benzo selenium oxazine derivative under room temperature, triethylamine alkaline condition, wherein, the mol ratio of ortho position functionalization aryl isonitrile, selenium powder and secondary amine is 1 ︰ 1.2 ~ 1.8 ︰ 1.2 ~ 1.8.
  2. 2. the preparation method of 2-as claimed in claim 1 amino benzo selenium oxazine derivative, is characterized in that: described ortho position functionalization aryl isonitrile is following structure
    Wherein, R 1substituting group is alkyl, aryl, halogen, amido or-oxyl; R 2substituting group is alkyl, aryl or alkoxyl group, and C substituting group is H, alkyl, aryl or alkoxyl group.
  3. 3. the preparation method of 2-as claimed in claim 2 amino benzo selenium oxazine derivative, it is characterized in that: described ortho position functionalization aryl isonitrile comprises 2-isocyano-methyl cinnamate, 2-isocyano-ethyl cinnamate, 4-chloro-2-isocyano-methyl cinnamate, 5-fluoro-2-isocyano-methyl cinnamate, 5-trifluoromethyl-2-isocyano-methyl cinnamate, 5-methyl-2-isocyano-methyl cinnamate or 3-(2-isocyanatophenyl)-1-phenyl third-2-alkene-1-ketone.
  4. 4. the preparation method of 2-as claimed in claim 1 amino benzo selenium oxazine derivative, is characterized in that: described secondary amine comprises piperidines, diethylamine or N-methylbenzylamine.
  5. 5. the preparation method of 2-as claimed in claim 1 amino benzo selenium oxazine derivative, is characterized in that: the mol ratio of described triethylamine and described ortho position functionalization aryl isonitrile is 1.5 ︰ 1.
  6. 6. the preparation method of 2-as claimed in claim 1 amino benzo selenium oxazine derivative, is characterized in that: with 1,2-ethylene dichloride as reaction solvent.
CN201510249209.6A 2015-05-15 2015-05-15 The preparation method of 2 amino benzo selenium oxazine derivatives Expired - Fee Related CN104803948B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201510249209.6A CN104803948B (en) 2015-05-15 2015-05-15 The preparation method of 2 amino benzo selenium oxazine derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201510249209.6A CN104803948B (en) 2015-05-15 2015-05-15 The preparation method of 2 amino benzo selenium oxazine derivatives

Publications (2)

Publication Number Publication Date
CN104803948A true CN104803948A (en) 2015-07-29
CN104803948B CN104803948B (en) 2017-03-15

Family

ID=53689187

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201510249209.6A Expired - Fee Related CN104803948B (en) 2015-05-15 2015-05-15 The preparation method of 2 amino benzo selenium oxazine derivatives

Country Status (1)

Country Link
CN (1) CN104803948B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106220586A (en) * 2016-07-15 2016-12-14 苏州大学 A kind of preparation method of 5 amido 1,2,4 selenium oxadiazole derivatives

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010254614A (en) * 2009-04-24 2010-11-11 Haruki Sashida Selenium-containing heterocyclic compound and use thereof

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010254614A (en) * 2009-04-24 2010-11-11 Haruki Sashida Selenium-containing heterocyclic compound and use thereof

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
HAJIME MAODA ET AL.: "A New Synthesis of lsoselenoureas by Imidoylation of Amines with Selenium and Isocyanides", 《TETRAHEDRON》 *
HARUKI SASHIDA ET AL.: "A Faclie and Practical Solvent-Free One-Pot Synthesis of (Z)-4-Methylene-3-selenaquinoline Derivatives from o-Ethynylanilines ans Isoselenocyanates", 《SYNTHESIS》 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106220586A (en) * 2016-07-15 2016-12-14 苏州大学 A kind of preparation method of 5 amido 1,2,4 selenium oxadiazole derivatives
CN106220586B (en) * 2016-07-15 2019-03-08 苏州大学 A kind of preparation method of 5- amido -1,2,4- selenium oxadiazole derivative

Also Published As

Publication number Publication date
CN104803948B (en) 2017-03-15

Similar Documents

Publication Publication Date Title
Wang et al. Cerium ammonium nitrate-catalyzed multicomponent reaction for efficient synthesis of functionalized tetrahydropyridines
Letessier et al. First Synthesis of Benzopyridoiodolium Salts and Twofold Buchwald-Hartwig Amination for the Total Synthesis of Quindoline
Chappell et al. En route to a plant scale synthesis of the promising antitumor agent 12, 13-desoxyepothilone B
Li et al. Synthesis of isothiocyanates by reaction of amines with phenyl chlorothionoformate via one-pot or two-step process
Jacobine et al. Three-component, one-flask synthesis of rhodanines (thiazolidinones)
Moafi et al. Three-component diastereoselective synthesis of stable 1, 4-diionic organosulfurs
Fang et al. Rapid and facile solvent-free mechanosynthesis in a cell lysis mill: preparation and mechanochemical complexation of aminobenzoquinones
CN106565742B (en) Indolone spiral shell tetrahydro thio-pyrylium analog derivative and its preparation method and application
CN102424645A (en) Method for synthesizing aromatic amide and aromatic methanol
Luo et al. Copper-catalyzed α-aminoxylation of 1, 3-dicarbonyl compounds with 2, 2, 6, 6-tetramethylpiperidine-1-oxyl (TEMPO) via an aerobic oxidative sp3 C–H bond activation
Zhu et al. One-pot three-component strategy for polysubstituted 2-aminothiazoles via ring opening of α-nitro epoxides
Li et al. S8‐Mediated One‐Pot Synthesis of Thioamides from Benzyl Chlorides and Amines
Meiries et al. A new synthetic route to p-methoxy-2, 6-disubstituted anilines and their conversion into N-heterocyclic carbene precursors
CN104803948A (en) Preparation method for 2-amino benzo phenoselenazine derivative
Wu et al. Silica Chloride Catalysed One‐pot Synthesis of 13‐Aryl‐indeno [1, 2‐b] naphtha [1, 2‐e] pyran‐12 (13H)‐ones under Solvent‐free Conditions
Duan et al. Convenient one-pot three-component synthesis of trifluoromethylated tetrahydrobenzo [g] chromene derivatives
Wu et al. An Efficient Copper-Catalyzed C (sp2)–S Formation Starting from Aryl Iodides and Tetramethylthiuram Monosulfide (TMTM)
Wang et al. Synthesis, structure and electrochemistry of new diferrocenyl pyridine derivatives
Lu et al. Iodine-Catalyzed C–N Cleavage of Tertiary Amines: Synthesis of Methylene-Bridged Bis-1, 3-dicarbonyl Compounds
Parthasarathy et al. Rhodium-catalyzed gram-scale synthesis of highly substituted pyridine derivatives
Yang et al. Acid-Mediated Synthesis of Chromeno [2, 3-b] pyridine Derivatives via Condensation of 2-Amino-3-formylchromones and 1-(Methylthio)-2-nitroenamine Derivatives
Tang et al. POxAP Precatalysts and the Negishi Cross-Coupling Reaction
CN104402839B (en) A kind of (E)-2,4,5-three replacement-(1-acrylic) azoles cyclics and preparation method thereof
Khoroshilov et al. Stereoselective synthesis of 2-[1-methylpyridin-2 (1H)-ylidene] malononitrile derivatives
Weibel et al. Direct Synthesis of Imines from g em-Dibromomethylaryl Derivatives: Application to Unsymmetrically Substituted Bipyridine Frameworks

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
EXSB Decision made by sipo to initiate substantive examination
SE01 Entry into force of request for substantive examination
C14 Grant of patent or utility model
GR01 Patent grant
CF01 Termination of patent right due to non-payment of annual fee
CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20170315

Termination date: 20200515