CN105294476A - 2-acyloxy acrylamide compound and synthesizing method thereof - Google Patents

2-acyloxy acrylamide compound and synthesizing method thereof Download PDF

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CN105294476A
CN105294476A CN201510763522.1A CN201510763522A CN105294476A CN 105294476 A CN105294476 A CN 105294476A CN 201510763522 A CN201510763522 A CN 201510763522A CN 105294476 A CN105294476 A CN 105294476A
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phenyl
acyloxy
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acrylamides
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CN105294476B (en
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许斌
王珏
高明春
刘秉新
谭启涛
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University of Shanghai for Science and Technology
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Abstract

The invention relates to a 2-acyloxy acrylamide compound and a synthesizing method thereof. The structural formula of the compound is seen in the specification, wherein R1 represents 4-chlorphenyl, 4-methyl phenyl, 4-methoxyphenyl, 3-methyl phenyl, 2-methoxyphenyl and phenyl, and R2 represents methyl and phenyl. The substituted 2-acyloxy acrylamide compound is a quite useful organic synthesized midbody. According to the method, raw materials are easy to obtain, reaction selectivity is high and conventional reaction agents are used. The compound has the advantages of being easy to operate, mild in condition, environmentally friendly in reaction and intermediate in yield and has quite good development prospects in industrial production.

Description

2-acyloxy acrylamides and synthetic method thereof
Technical field
The present invention relates to a kind of 2-acyloxy acrylamides and synthetic method thereof.
Background technology
Acrylamides and its derivative because of its have compared with high biological activity and potential physiological and pharmacological active, get more and more people's extensive concerning.Such as, acrylamides has good effect for anti-malignant cell proliferation, as to vascular endothelial proliferation, inhibited (see reference document: Shi, L.etal. eur.J.Med.Chem. 2012, 47, 585).Acrylamides also can as the carrier of some medicines, such as can as the transport molecules of ABCG2, MRP1 and Pgp (see reference document: Henrich, C.J.Patent:WO2009/88831A2,2009).Equally, acrylamides can also (see reference document: Sarikaya, B.B.etal. as a kind of inhibitor of enzyme phytochemLett. 2012, 5, 367) and a kind of antimycotic medicine (see reference document: Chen, H-S.etal. chem.Nat.Compd. 2011, 47, 257).Meanwhile, acrylamides occupies very important status in chemical field, particularly have in coating, cosmetics of everyday use, photosensitive resin, tackiness agent, solidifying agent, medical material etc. are a lot of widespread use (see reference document: Wang Junfeng etc., coatings industry, 2011, 41, 57).In addition, acrylamides or the very useful synthon of a class, can be used for building structure other organic compound more complicated and changeable.Such as in Diels-Alder reaction, 1,3-cycloaddition reaction and Friedel-Craft reaction etc.
The method of the synthesis 2-acyloxy acrylamides reported in document mainly contains following several:
(1) people such as Elgomati generates corresponding 2-acyloxy acrylamides in raw material open loop under hydrochloric acid effect of the dioxolane with a kind of replacement of report in 1977, but (see reference the more difficult preparation of the method raw material ratio document: Elgomati, T.etal. chem.Ber. 1977, 110, 1603).
(2) people such as Yasuhiro reported the method for synthesizing corresponding 2-acyloxy acrylamides with the amine of acrylate chloride and various replacement in 1969, but the limitation of substrate is very large, and the reaction times is longer, and (see reference document: Yasuhiro, C.etal. bull.Chem.Soc.Jpn. 1969, 42, 224).
(3) people such as Sodum reported in 1986 and generates the method for corresponding 2-acyloxy acrylamides with reaction under Pyrimdinone raw material and the condition of diacetyl oxide at sodium hydroxide, but the method is for the limitation of substrate, and comparatively large (see reference document: Sodum, R.S.etal. j.Heterocycl.Chem. 1986, 23, 1239).
(4) people such as Norton reported in 2012 and in Nitromethane 99Min., is heated to isonitrile and carboxylic acid the method that 40 DEG C generate corresponding 2-acyloxy acrylamides.But the method can only generate the identical product of substituting group, product limitation is comparatively large, and (see reference document: Norton, J.R.etal. tetrahedron. 2012, 68, 10236).
(5) people such as Andrea reported the three components reaction under visible light catalytic in 2014, and (see reference document: Andream, B.etal. to use diazo ketone, carboxylic acid and isonitrile to generate the method for 2-acyloxy acrylamides j.Org.Chem. 2014, 79,3615).
In sum, the synthetic method of 2-acyloxy acrylamides has above several, but substrate all relative complex of these reactions, and limitation is larger, often will be obtained by reacting by a few step, or these reaction needed strong acid or highly basic etc. compare exacting terms.
Summary of the invention
An object of the present invention is to provide a kind of 2-acyloxy acrylamides,
Two of object of the present invention is the synthetic method providing this compounds a kind of.
For achieving the above object, the reaction mechanism that the inventive method adopts is:
R 1for phenyl, rubigan, p-methylphenyl, p-methoxyphenyl, an aminomethyl phenyl or o-methoxyphenyl;
R 2for methyl or phenyl.
A kind of 2-acyloxy acrylamides, is characterized in that the structural formula of this compound is:
, wherein, R 1for chloro-phenyl-, aminomethyl phenyl, p-methoxy-phenyl or phenyl; R 2for methyl or phenyl.
A kind of method preparing 2-acyloxy acrylamides according to claim 1, it is characterized in that the method has following steps: under inert atmosphere protection, by alkynes, tert-butyl isonitrile, carboxylic acid, palladium, silver suboxide and three (o-methyl-phenyl-) phosphine by 1:(1.0 ~ 8.0): (2.0 ~ 8.0): (0.01 ~ 0.05): (1.5 ~ 5.0): the mol ratio of (0.1 ~ 0.3) joins in chlorobenzene, at 20 DEG C ~ 80 DEG C, stirring reaction disappears to reaction raw materials; After reaction terminates, wash respectively, be extracted with ethyl acetate product with water and saturated aqueous common salt, organic phase obtains crude product after removing solvent after drying; This crude product, through separation and purification, namely obtains the corresponding 2-acyloxy acrylamides replaced; Described alkynes structural formula is: ; The structural formula of described carboxylic acid is: .
The 2-acyloxy acrylamides of replacement of the present invention is the intermediate of the important organic reaction of a class, and dissimilar organic chemical reactions can occur.Such as this compounds can pass through the compound of the synthesis series of complexes such as 1,3-cycloaddition reaction, Friedel-Craft reaction and rearrangement reaction.About reaction is exemplified below: the acrylamides of such 2-acyloxy has synthesized the derivative of a series of pyrroles and succimide through intramolecular rearrangement reaction, and (see reference document: AndreaB.etal. org.Lett. 2009, 11, 4068).
In addition, the reaction that deacylated tRNA base can also occur such acrylamides generates the product of alpha-carbonyl acid amides, and (see reference document: AndreaB.etal. angew.Chem.Int.Ed. 2013, 52, 2096).
The inventive method raw material is simple and easy to get, and uses conventional reaction solvent, simple to operate, mild condition, reaction environmental protection, by the time outstanding in productive rate, has good development prospect in the industrial production.
Embodiment
Embodiment one: ( z)-3-(tert-butylamino)-1-(4-chloro-phenyl-)-3-carbonyl third-1-alkene-2-yl acetate
( z)-3-(tert-butylamino)-1-(4-chloro-phenyl-)-3-carbonyl third-1-alkene-2-yl acetate adopts following step: 1. in 1000 milliliters of reactors, add 20.5 grams to chlorobenzene acetylene by the mol ratio of 1:1.5:2.0:0.01:1.5:0.1,18.7 gram tert-butyl isonitrile, 18.0 gram acetic acid, 0.3 gram of palladium, 52 grams of silver suboxides, 4.6 gram of three (o-methyl-phenyl-) phosphine, then add 500 milliliters of chlorobenzenes, be heated to 40 DEG C.Follow the tracks of reaction by thin-layer chromatography method, disappear to reaction raw materials; 2., after reaction terminates, the cancellation that adds water in system is reacted, and is extracted with ethyl acetate product, uses saturated common salt water washing, remove solvent, obtain crude product after drying with Rotary Evaporators; 3. crude product column chromatography (sherwood oil: ethyl acetate=10:1) purifying, obtain 32.8 grams ( z)-3-(tert-butylamino)-1-(4-chloro-phenyl-)-3-carbonyl third-1-alkene-2-yl acetate, productive rate is 74%.Fusing point: 164 DEG C
IR(KBr,cm -1 ):3352,3060,2981,1767,1629,1538,1456,1364,1360,1196,1105,1010,939,830,753,668,584,491.
1 HNMR(CDCl 3 ,500MHz): δ7.41(d, J=8.5Hz,2H),7.33(d, J=8.5Hz,2H),7.05(s,1H),5.80(br,1H),2.34(s,3H),2.28(s,3H),1.40(s,9H).
13 CNMR(CDCl 3 ,125MHz): δ167.7,161.7,141.2,135.0,131.2,130.6,129.1,121.3,51.8,28.7,21.0.
LC-MS(ESI)m/z:296[M +H].
HRMS(ESI)m/z:calcdforC 15H 19NO 3Cl[M +H]296.1046,found276.1048.
Embodiment two: ( z)-3-(tert-butylamino)-3-carbonyl-1-(p-methylphenyl) the third-1-alkene-2-yl acetate
( z)-3-(tert-butylamino)-3-carbonyl-1-(p-methylphenyl) the third-1-alkene-2-yl acetate adopts following step: 1. in 1000 milliliters of reactors, add 17.4 grams to methylbenzene acetylene by the mol ratio of 1:4.5:6.0:0.05:3.5:0.2,56.1 gram tert-butyl isonitrile, 54 grams of acetic acid, 1.7 grams of palladium, 121.7 grams of silver suboxides, 9.1 gram of three (o-methyl-phenyl-) phosphine, then add 500 milliliters of chlorobenzenes, be heated to 80 DEG C.Follow the tracks of reaction by thin-layer chromatography method, disappear to reaction raw materials; 2., after reaction terminates, the cancellation that adds water in system is reacted, and is extracted with ethyl acetate product, uses saturated common salt water washing, remove solvent, obtain crude product after drying with Rotary Evaporators; 3. crude product column chromatography (sherwood oil: ethyl acetate=10:1) purifying, obtain 31.8 grams ( z)-3-(tert-butylamino)-3-carbonyl-1-(p-methylphenyl) the third-1-alkene-2-yl acetate, productive rate is 77%.Fusing point: 158 DEG C
IR(KBr,cm -1 ):3324,2966,2924,1769,1633,1540,1447,1366,1310,1193,1009,937,812.
1 HNMR(CDCl 3 ,500MHz): δ7.37(d, J=8.0Hz,2H),7.16(d, J=8.0Hz,3H),7.08(s,1H),5.81(br,1H),2.34(s,3H),2.28(s,3H),1.40(s,9H).
13 CNMR(CDCl 3 ,125MHz): δ168.0,162.1,140.1,139.4,129.8,129.6,129.5,122.6,51.7,28.8,21.5,21.0.
LC-MS(ESI)m/z:276[M +H].
HRMS(ESI)m/z:calcdforC 16H 22NO 3[M +H]276.1588,found276.1594.
Embodiment three: ( z)-3-(tert-butylamino)-1-(4-p-methoxy-phenyl)-3-carbonyl third-1-alkene-2-yl acetate
( z)-3-(tert-butylamino)-1-(4-p-methoxy-phenyl)-3-carbonyl third-1-alkene-2-yl acetate adopts following step: 1. in 1000 milliliters of reactors, add 19.8 grams to Methoxy-phenylacetylene by the mol ratio of 1:8.0:4.0:0.03:5.0:0.3,99.7 tert-butyl isonitriles, 36.0 gram acetic acid, 1.0 grams of palladium, 173.8 grams of silver suboxides, 13.7 gram of three (o-methyl-phenyl-) phosphine, then add 500 milliliters of chlorobenzenes, be heated to 50 DEG C.Follow the tracks of reaction by thin-layer chromatography method, disappear to reaction raw materials; 2., after reaction terminates, the cancellation that adds water in system is reacted, and is extracted with ethyl acetate product, uses saturated common salt water washing, remove solvent, obtain crude product after drying with Rotary Evaporators; 3. crude product column chromatography (sherwood oil: ethyl acetate=10:1) purifying, obtain 32.3 grams ( z)-3-(tert-butylamino)-1-(4-p-methoxy-phenyl)-3-carbonyl third-1-alkene-2-yl acetate, productive rate is 74%.Fusing point: 110 DEG C.
3397,2972,2931,1752,1675,1643,1603,1518,1453,1367,1296,1252,1183,1105,1024,831,537.
1 HNMR(CDCl 3 ,500MHz): δ7.43(d, J=8.5Hz,2H),7.06(s,1H),6.88(d, J=8.5Hz,2H),5.79(br,1H),3.80(s,3H),2.29(s,3H),1.40(s,9H).
13 CNMR(CDCl 3 ,125MHz): δ162.1,160.2,139.2,131.1,125.2,122.2,114.3,55.3,51.6,28.8,21.0.
LC-MS(ESI)m/z:292[M +H].
HRMS(ESI)m/z:calcdforC 16H 22NO 4[M +H]292.1543,found292.1537.
Embodiment four: ( z)-3-(tert-butylamino) aminomethyl phenyl between-3-carbonyl-1-() the third-1-alkene-2-yl acetate
( z)-3-(tert-butylamino) aminomethyl phenyl between-3-carbonyl-1-() the third-1-alkene-2-yl acetate adopts following step: 1. in 1000 milliliters of reactors, add methylbenzene acetylene between 17.4 grams by the mol ratio of 1:1.0:8.0:0.05:5.0:0.2,12.5 gram tert-butyl isonitrile, 72 grams of acetic acid, 1.7 grams of palladium, 173.8 grams of silver suboxides, 9.1 gram of three (o-methyl-phenyl-) phosphine, then add 500 milliliters of chlorobenzenes, be heated to 80 DEG C.Follow the tracks of reaction by thin-layer chromatography method, disappear to reaction raw materials; 2., after reaction terminates, the cancellation that adds water in system is reacted, and is extracted with ethyl acetate product, uses saturated common salt water washing, remove solvent, obtain crude product after drying with Rotary Evaporators; 3. crude product column chromatography (sherwood oil: ethyl acetate=10:1) purifying, obtain 34.7 grams ( z)-3-(tert-butylamino) aminomethyl phenyl between-3-carbonyl-1-() the third-1-alkene-2-yl acetate, productive rate is 84%.Fusing point: 119 DEG C.
3316,3059,2967,2920,1766,1634,1541,1479,1442,1364,1312,1193,1113,1008,907,784,689.
1 HNMR(CDCl 3 ,500MHz): δ7.30(d, J=7.5Hz,1H),7.27(s,1H),7.24(t, J=7.5Hz,1H),7.13(d, J=7.5Hz,1H),7.08(s,1H),5.82(br,1H),2.33(s,3H),2.28(s,3H),1.41(s,9H).
13 CNMR(CDCl 3 ,125MHz): δ167.8,161.8,140.4,138.2,132.4,130.2,129.8,128.5,126.3,122.6,51.6,28.6,21.4,20.9.
LC-MS(ESI)m/z:276[M +H].
HRMS(ESI)m/z:calcdforC 16H 22NO 3[M +H]276.1594,found276.1589.
Embodiment five: ( z)-3-(tert-butylamino)-1-(2-p-methoxy-phenyl)-3-carbonyl third-1-alkene-2-yl acetate
( z)-3-(tert-butylamino)-1-(2-p-methoxy-phenyl)-3-carbonyl third-1-alkene-2-yl acetate adopts following step: 1. in 1000 milliliters of reactors, add methylbenzene acetylene between 19.8 grams by the mol ratio of 1:6.0:5.0:0.01:4.5:0.1,74.8 gram tert-butyl isonitrile, 45.0 gram acetic acid, 0.3 gram of palladium, 156.4 grams of silver suboxides, 4.6 gram of three (o-methyl-phenyl-) phosphine, then add 500 milliliters of chlorobenzenes, be heated to 50 DEG C.Follow the tracks of reaction by thin-layer chromatography method, disappear to reaction raw materials; 2., after reaction terminates, the cancellation that adds water in system is reacted, and is extracted with ethyl acetate product, uses saturated common salt water washing, remove solvent, obtain crude product after drying with Rotary Evaporators; 3. crude product column chromatography (petrol ether/ethyl acetate=10:1) purifying, obtain 39.3 grams ( z)-3-(tert-butylamino)-1-(2-p-methoxy-phenyl)-3-carbonyl third-1-alkene-2-yl acetate, productive rate is 90%.Fusing point: 118 DEG C.
3326,2967,2929,1774,1664,1631,1524,1491,1452,1399,1365,1295,1254,1180,1106,1018,926,751,668.
1 HNMR(CDCl 3 ,500MHz): δ7.55-7.49(m,1H),7.39(s,1H),7.32-7.26(m,1H),6.95-6.90(t, J=7.5Hz,1H),6.89(d, J=8.0Hz,1H),5.83(br,1H),3.83(s,3H),2.23(s,3H),1.41(s,9H).
13 CNMR(CDCl 3 ,125MHz): δ168.1,162.0,157.4,140.7,130.3,129.1,121.5,120.4,116.9,110.8,55.5,51.5,28.6,20.8.
LC-MS(ESI)m/z:314[M +Na].
HRMS(ESI)m/z:calcdforC 16H 22NO 4[M +H]292.1543,found292.1537.
Embodiment six: ( z)-3-(tert-butylamino)-3-carbonyl-1-phenyl third-1-alkene-2-yl acetate
( z)-3-(tert-butylamino)-3-carbonyl-1-phenyl third-1-alkene-2-yl acetate adopts following step: 1. in 1000 milliliters of reactors, add 15.3 grams of phenylacetylenes by the mol ratio of 1:2.0:3.0:0.01:2.5:0.1,25.0 gram tert-butyl isonitrile, 27.0 gram acetic acid, 0.3 palladium, 86.9 gram silver suboxide, 4.6 gram of three (o-methyl-phenyl-) phosphine, then add 500 milliliters of chlorobenzenes, be heated to 30 DEG C.Follow the tracks of reaction by thin-layer chromatography method, disappear to reaction raw materials; 2., after reaction terminates, the cancellation that adds water in system is reacted, and is extracted with ethyl acetate product, uses saturated common salt water washing, remove solvent, obtain crude product after drying with Rotary Evaporators; 3. crude product column chromatography (petrol ether/ethyl acetate=10:1) purifying, obtain 32.5 grams ( z)-3-(tert-butylamino)-3-carbonyl-1-phenyl third-1-alkene-2-yl acetate, productive rate is 83%.Fusing point: 138 DEG C.
3351,3060,2970,2927,1766,1636,1546,1449,1363,1294,1200,1113,1041,1008,935,876,766,687,614.
1 HNMR(CDCl 3 ,500MHz): δ7.48(d, J=7.25Hz,2H),7.40-7.28(m,3H),7.10(s,1H),5.82(br,1H),2.28(s,3H),1.41(s,9H).
13 CNMR(CDCl 3 ,125MHz): δ167.8,161.8,140.6,132.5,129.3,129.0,128.7,122.4,51.6,28.6,20.9.
LC-MS(ESI)m/z:262[M +H].
HRMS(ESI)m/z:calcdforC 15H 20NO 3[M +H]262.1438,found292.1432.
Embodiment seven: ( z)-3-(tert-butylamino)-3-carbonyl-1-phenyl third-1-alkene-2-yl benzoic acid ester
( z)-3-(tert-butylamino)-3-carbonyl-1-phenyl third-1-alkene-2-yl benzoic acid ester adopts following step: 1. in 1000 milliliters of reactors, add 15.3 grams of phenylacetylenes by the mol ratio of 1:3.0:4.0:0.05:5.5:0.15,37.4 gram tert-butyl isonitrile, 73.3 gram phenylformic acid, 1.7 grams of palladium, 191.2 grams of silver suboxides, 6.8 gram of three (o-methyl-phenyl-) phosphine, then add 500 milliliters of chlorobenzenes, be heated to 80 DEG C.Follow the tracks of reaction by thin-layer chromatography method, disappear to reaction raw materials; 2., after reaction terminates, the cancellation that adds water in system is reacted, and is extracted with ethyl acetate product, uses saturated common salt water washing, remove solvent, obtain crude product after drying with Rotary Evaporators; 3. crude product column chromatography (petrol ether/ethyl acetate=10:1) purifying, obtain 39.8 grams ( z)-3-(tert-butylamino)-3-carbonyl-1-phenyl third-1-alkene-2-yl benzoic acid ester, productive rate is 82%.Fusing point: 148 DEG C.
3428,3324,3067,2970,1743,1637,1546,1452,1314,1251,1119,1056,1022,910,756,700.
1 HNMR(d 6 -acetone,500MHz): δ8.20-8.15(m,2H),7.78-7.72(m,1H),7.65-7.57(m,4H),7.36-7.26(m,3H),7.21(s,1H),7.11(br,1H),1.42(s,9H).
13 CNMR(d 6 -acetone,125MHz): δ164.6,162.6,142.8,134.9,133.9,131.0,130.3,130.0,129.8,129.7,129.5,122.0,52.0,28.8.
LC-MS(ESI)m/z:324[M +H].
HRMS(ESI)m/z:calcdforC 20H 22NO 3[M +H]324.1594,found324.1587。

Claims (2)

1. a 2-acyloxy acrylamides, is characterized in that the structural formula of this compound is:
, wherein, R 1for chloro-phenyl-, aminomethyl phenyl, p-methoxy-phenyl or phenyl; R 2for methyl or phenyl.
2. prepare the method for 2-acyloxy acrylamides according to claim 1 for one kind, it is characterized in that the method has following steps: under inert atmosphere protection, by alkynes, tert-butyl isonitrile, carboxylic acid, palladium, silver suboxide and three (o-methyl-phenyl-) phosphine by 1:(1.0 ~ 8.0): (2.0 ~ 8.0): (0.01 ~ 0.05): (1.5 ~ 5.0): the mol ratio of (0.1 ~ 0.3) joins in chlorobenzene, at 20 DEG C ~ 80 DEG C, stirring reaction disappears to reaction raw materials; After reaction terminates, wash respectively, be extracted with ethyl acetate product with water and saturated aqueous common salt, organic phase obtains crude product after removing solvent after drying; This crude product, through separation and purification, namely obtains the corresponding 2-acyloxy acrylamides replaced; Described alkynes structural formula is: ; The structural formula of described carboxylic acid is: .
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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106146359A (en) * 2016-07-29 2016-11-23 江西师范大学 The gentle efficient preparation method of α acyloxy acrylamide compound and the application in amide and Peptide systhesis thereof
CN107056635A (en) * 2017-06-09 2017-08-18 广西师范大学 A kind of synthetic method of alkynyl amide class compound
CN114989032A (en) * 2022-06-14 2022-09-02 安徽大学 Method for synthesizing imide derivatives

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
ANDREA BASSO ET AL.: "Isocyanides and Arylacetic Acids: Synthesis and Reactivity of 3-Aryl-2-acyloxyacrylamides,an Example of Serendipity-Oriented Synthesis", 《ORGANIC LETTERS》 *
ANDREABASSO: "KeteneThree-ComponentReaction:AMetal-FreeMulticomponent ApproachtoStereodefinedCaptodativeOlefins", 《ANGEW.CHEM.INT.ED.》 *
SILVIA GARBARINO ET AL.: "Toward a Green Atom Economy: Development of a Sustainable Multicomponent Reaction", 《SYNTHESIS》 *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106146359A (en) * 2016-07-29 2016-11-23 江西师范大学 The gentle efficient preparation method of α acyloxy acrylamide compound and the application in amide and Peptide systhesis thereof
CN106146359B (en) * 2016-07-29 2017-11-24 江西师范大学 Gently efficient preparation method and its application in acid amides and Peptide systhesis of α acyloxy acrylamide compound
CN107056635A (en) * 2017-06-09 2017-08-18 广西师范大学 A kind of synthetic method of alkynyl amide class compound
CN114989032A (en) * 2022-06-14 2022-09-02 安徽大学 Method for synthesizing imide derivatives
CN114989032B (en) * 2022-06-14 2024-04-12 安徽大学 Method for synthesizing imide derivative

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