CN111592501B - Synthesis method of 1, 3-oxazine hydroxylate - Google Patents
Synthesis method of 1, 3-oxazine hydroxylate Download PDFInfo
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- oxazine
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- copper salt
- allyl ester
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- KGWNRZLPXLBMPS-UHFFFAOYSA-N 2h-1,3-oxazine Chemical compound C1OC=CC=N1 KGWNRZLPXLBMPS-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 238000001308 synthesis method Methods 0.000 title description 3
- -1 aryl formyl imine allyl ester Chemical class 0.000 claims abstract description 33
- 150000001879 copper Chemical class 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 10
- 229910052709 silver Inorganic materials 0.000 claims abstract description 10
- 239000004332 silver Substances 0.000 claims abstract description 10
- 230000002194 synthesizing effect Effects 0.000 claims abstract description 10
- 239000003960 organic solvent Substances 0.000 claims abstract description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 5
- 238000010438 heat treatment Methods 0.000 claims abstract description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical group [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 claims description 7
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 3
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims description 3
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 6
- 230000000975 bioactive effect Effects 0.000 abstract description 3
- 150000002148 esters Chemical class 0.000 description 4
- 150000004895 1,3-oxazines Chemical class 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 description 2
- 229940071536 silver acetate Drugs 0.000 description 2
- CLDWGXZGFUNWKB-UHFFFAOYSA-M silver;benzoate Chemical compound [Ag+].[O-]C(=O)C1=CC=CC=C1 CLDWGXZGFUNWKB-UHFFFAOYSA-M 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 102000013455 Amyloid beta-Peptides Human genes 0.000 description 1
- 108010090849 Amyloid beta-Peptides Proteins 0.000 description 1
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- DZHSAHHDTRWUTF-SIQRNXPUSA-N amyloid-beta polypeptide 42 Chemical compound C([C@@H](C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@H](C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)NCC(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(O)=O)[C@@H](C)CC)C(C)C)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC(O)=O)C(C)C)C(C)C)C1=CC=CC=C1 DZHSAHHDTRWUTF-SIQRNXPUSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- SBTSVTLGWRLWOD-UHFFFAOYSA-L copper(ii) triflate Chemical compound [Cu+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F SBTSVTLGWRLWOD-UHFFFAOYSA-L 0.000 description 1
- 229960003280 cupric chloride Drugs 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000002532 enzyme inhibitor Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 229940126586 small molecule drug Drugs 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/06—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings
- C07D265/08—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
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
A method for synthesizing 1, 3-oxazine hydroxylate comprises the following steps: 1) Sequentially adding aryl formyl imine allyl ester, silver carboxylate and copper salt into an organic solvent; 2) Heating to a proper temperature to obtain the 1, 3-oxazine compound containing carboxyl. The invention creatively uses aryl formyl imine allyl ester, silver carboxylate and copper salt to prepare novel 1, 3-oxazine compound containing hydroxyl. Therefore, the invention has good practical value and has important reference significance for developing 1, 3-oxazine important bioactive molecules.
Description
Technical Field
The invention relates to a method for synthesizing 1, 3-oxazine hydroxylate, and belongs to the technical field of organic synthesis.
Background
1, 3-oxazines are an important class of biologically active molecules, e.g., some beta amyloid precursor protein cleaving enzyme inhibitors contain a 1, 3-oxazine structure. In the design and synthesis of the innovative small molecule drug, organic small molecules with potential biological activity can be very easily obtained by deriving the active skeleton. Since hydroxyl is a functional group which is easy to derive and convert, the hydroxyl or the derivative thereof is introduced into the 1, 3-oxazine bioactive molecule, which is helpful for the further bioactivity research of related compounds. Currently, the synthesis method of 1, 3-oxazines is the condensation preparation of amino alcohols with carbonyl compounds (chem. Eur J,2008,14, 3653), and this strategy limits the preparation of hydroxyl-containing 1, 3-oxazines.
Disclosure of Invention
The invention aims to solve the technical problem of preparing a 1, 3-oxazine compound containing hydroxyl by using arylformyl imine allyl-homoester, silver carboxylate and copper salt.
In order to solve the technical problem, the invention adopts the following technical scheme:
a method for synthesizing 1, 3-oxazine hydroxylate comprises the following steps: 1) Sequentially adding aryl formyl imine allyl ester, silver carboxylate and copper salt into an organic solvent; 2) Heating to a proper temperature to obtain the 1, 3-oxazine compound containing carboxyl, wherein the chemical reaction formula is as follows:
in the above formulas:
ar is substituted by one or more of phenyl, p-methylphenyl, m-ethylphenyl, p-chlorophenyl, m-bromophenyl, p-bromophenyl, m-fluorophenyl, p-tert-butylphenyl, m-tert-butylphenyl and naphthyl;
r is one or more of methyl, ethyl, propyl, butyl, p-methylphenyl, phenyl, m-methylphenyl, naphthyl and trifluoromethyl substituted.
The copper salt is selected from copper acetate, copper trifluoromethanesulfonate, cuprous bromide, cupric chloride, cuprous iodide and cuprous chloride.
The copper salt is preferably copper acetate.
The organic solvent is selected from 1, 2-dichloroethane, acetonitrile, N-dimethylformamide, ethyl acetate, N-hexane, N-nonane, tetrahydrofuran and cyclohexane.
The organic solvent is preferably 1, 2-dichloroethane.
The heating temperature is 20-100 deg.C, and the maintaining time is 1-48 hr.
The appropriate temperature for the heating is preferably 80 ℃ and the holding time is 24 hours.
The arylcarboximide high allyl ester: silver carboxylate: the molar weight ratio of the copper salt is as follows: 1:1 to 4:0.01 to 0.5.
The arylcarboximide high allyl ester: silver carboxylate: the molar weight ratio of the copper salt is preferably: 1:2:0.2. The beneficial effect of adopting above-mentioned technical scheme is:
the invention creatively uses aryl formyl imine allyl ester, silver carboxylate and copper salt to prepare novel 1, 3-oxazine compound containing hydroxyl. Therefore, the invention has good practical value and has important reference significance for developing 1, 3-oxazine important bioactive molecules.
Detailed Description
The present invention will be further described with reference to specific examples, but it should not be construed that the scope of the above-described subject matter of the present invention is limited to the following examples, and that all the technologies implemented based on the above-described contents of the present invention belong to the scope of the present invention.
The first embodiment is as follows:
a method for synthesizing 1, 3-oxazine hydroxylate comprises the following steps: 1) P-methyl benzoylimine homoallylic ester is taken as a substrate, silver acetate is taken as a carboxyl reagent, copper acetate is taken as copper salt, and acetonitrile is taken as a reaction solvent; 2) P-methylbenzimido homoallyl ester (37.8mg, 0.2mmol), silver acetate (66.8mg, 0.4mmol), and copper acetate (7.2mg, 0.04mmol) were sequentially added to stirred 1, 2-dichloroethane (2 mL), reacted at 80 ℃ for 24 hours, and then subjected to extraction, drying, concentration, and silica gel column chromatography to obtain a colorless liquid (37.1mg, 75%) of chemical reaction formula 1:
the product detection data were as follows:
1 H NMR(400MHz,CDCl 3 )δ7.79(d,J＝8.1Hz,2H),7.16(d,J＝8.0Hz,2H),4.47–4.40(m,1H),4.34–4.25(m,2H),4.16–4.08(m,1H),3.85–3.76(m,1H),2.36(s,3H),2.10(s,3H),2.09–2.02(m,1H),1.85–1.72(m,1H)； 13 C NMR(101MHz,CDCl 3 )δ171.2,156.2,140.8,131.1,128.9,127.2,68.1,64.0,50.7,24.9,21.6,21.2。
example two:
a method for synthesizing 1, 3-oxazine hydroxylate comprises the following steps: 1) P-methyl benzoylimine homoallylic ester is taken as a substrate, silver benzoate is taken as a carboxyl reagent, copper acetate is taken as copper salt, and acetonitrile is taken as a reaction solvent; 2) P-methylbenzimido homoallyl ester (37.8mg, 0.2mmol), silver benzoate (91.5mg, 0.4mmol), and copper acetate (7.2mg, 0.04mmol) were sequentially added to stirred 1, 2-dichloroethane (2 mL), reacted at 80 ℃ for 24 hours, and then subjected to extraction, drying, concentration, and silica gel column chromatography to obtain a colorless liquid (50.2mg, 81%), chemical reaction formula 2:
the product detection data were as follows:
1 H NMR(400MHz,CDCl 3 )δ7.79(d,J＝8.1Hz,2H),7.16(d,J＝8.0Hz,2H),4.47–4.40(m,1H),4.34–4.25(m,2H),4.16–4.08(m,1H),3.85–3.76(m,1H),2.36(s,3H),2.10(s,3H),2.09–2.02(m,1H),1.85–1.72(m,1H)； 13 C NMR(101MHz,CDCl 3 )δ166.6,156.4,140.9,133.1,131.0,130.3,129.8,128.9,128.5,127.2,68.4,64.1,50.8,25.1,21.6。
Claims (5)
1. a method for synthesizing 1, 3-oxazine hydroxylate is characterized in that: it comprises the following steps: 1) Sequentially adding aryl formyl imine allyl ester, silver carboxylate and copper salt into an organic solvent; 2) Heating to a proper temperature to obtain the 1, 3-oxazine compound containing carboxyl, wherein the chemical reaction formula is as follows:
in the above formulas:
ar is phenyl, p-methylphenyl, m-ethylphenyl, p-chlorophenyl, m-bromophenyl, p-bromophenyl, m-fluorophenyl, p-tert-butylphenyl, m-tert-butylphenyl or naphthyl;
r is methyl, ethyl, propyl, butyl, p-methylphenyl, phenyl, m-methylphenyl, naphthyl or trifluoromethyl;
the copper salt is selected from copper acetate;
the organic solvent is selected from 1, 2-dichloroethane, acetonitrile,N,N-dimethylformamide, ethyl acetate, n-hexane, n-nonane, tetrahydrofuran or cyclohexane;
the proper temperature is 20-100 ℃, and the maintaining time is 1-48 hours.
2. The method for synthesizing the 1, 3-oxazine hydroxylate according to claim 1, wherein: the organic solvent is selected from 1, 2-dichloroethane.
3. The method for synthesizing the 1, 3-oxazine hydroxylate according to claim 1, wherein: the suitable temperature is 80 ℃ and the holding time is 24 hours.
4. The method for synthesizing the 1, 3-oxazine hydroxylate according to claim 1, wherein: the arylcarboximide high allyl ester: silver carboxylate: the molar weight ratio of the copper salt is as follows: 1: 1. -4: 0.01 to 0.5.
5. The method for synthesizing 1, 3-oxazine hydroxylate according to claim 1 or 4, wherein: the arylcarboximide high allyl ester: silver carboxylate: the molar weight ratio of the copper salt is as follows: 1:2:0.2.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05112544A (en) * | 1991-10-18 | 1993-05-07 | Yamanouchi Pharmaceut Co Ltd | 4,6-dioxo-1, 3-oxazine-2-carboxylic acid derivative |
| EP1213328A1 (en) * | 2000-12-08 | 2002-06-12 | Evotec OAI AG | Oxazine derivatives |
| CN101440070A (en) * | 2008-09-12 | 2009-05-27 | 华东师范大学 | N-substituted-2-bezilidene-3,4-dihydrobenzo [1,4] oxazine compounds and preparation thereof |
| CN104130204A (en) * | 2014-07-03 | 2014-11-05 | 浙江大学 | Method for preparing N-sulfonyl-1,4-oxazine derivative |
-
2020
- 2020-06-29 CN CN202010603883.0A patent/CN111592501B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05112544A (en) * | 1991-10-18 | 1993-05-07 | Yamanouchi Pharmaceut Co Ltd | 4,6-dioxo-1, 3-oxazine-2-carboxylic acid derivative |
| EP1213328A1 (en) * | 2000-12-08 | 2002-06-12 | Evotec OAI AG | Oxazine derivatives |
| CN101440070A (en) * | 2008-09-12 | 2009-05-27 | 华东师范大学 | N-substituted-2-bezilidene-3,4-dihydrobenzo [1,4] oxazine compounds and preparation thereof |
| CN104130204A (en) * | 2014-07-03 | 2014-11-05 | 浙江大学 | Method for preparing N-sulfonyl-1,4-oxazine derivative |
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