CN105294476B - The synthetic method of 2 acyloxy acrylamides - Google Patents

The synthetic method of 2 acyloxy acrylamides Download PDF

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CN105294476B
CN105294476B CN201510763522.1A CN201510763522A CN105294476B CN 105294476 B CN105294476 B CN 105294476B CN 201510763522 A CN201510763522 A CN 201510763522A CN 105294476 B CN105294476 B CN 105294476B
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acrylamides
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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 present invention relates to a kind of synthetic method of 2 acyloxy acrylamides.The structural formula of the compound is：Wherein, R1For 4 chlorphenyls, 4 aminomethyl phenyls, 4 methoxyphenyls, 3 aminomethyl phenyls, 2 methoxyphenyls, phenyl；R2For methyl, phenyl.2 acyloxy acrylamides of the present invention are a kind of highly useful organic synthesis intermediates.The inventive method raw material is simple and easy to get, and reaction selectivity is high, and uses conventional reaction dissolvent.It is simple to operate, mild condition, reaction environmental protection, when outstanding in yield, there is good development prospect in the industrial production.

Description

The synthetic method of 2- acyloxy acrylamides
Technical field
The present invention relates to a kind of synthetic method of 2- acyloxy acrylamides.
Background technology
The relatively high bioactivity and potential physiological and pharmacological that acrylamides and its derivative have by it are lived Property, get more and more people's extensive concerning.For example, acrylamides have good effect for anti-malignant cell proliferation, It is such as inhibited to vascular endothelial proliferation that (see reference document：Shi,L.et al.Eur.J.Med.Chem.2012, 47,585).Acrylamides can also be as the carrier of some medicines, such as can be used as ABCG2, MRP1 and Pgp Transport molecules (see reference document：Henrich,C.J.Patent:WO2009/88831A2,2009).Equally, acrylic amide Compound is also used as a kind of inhibitor of enzyme, and (see reference document：Sarikaya,B.B.et al.Phytochem Lett.2012,5,367) and a kind of antimycotic medicine (see reference document：Chen,H-S.et al.Chem.Nat.Compd. 2011,47,257).Meanwhile acrylamides occupy very important status in chemical field, particularly applying Many aspects such as material, daily chemical product, photosensitive resin, adhesive, curing agent, medical material have extensively using (see reference document： Wang Junfeng etc., coatings industry, 2011,41,57).In addition, acrylamides or a kind of highly useful synthesis Son, other organic compounds more complicated and changeable available for structure structure.Such as reacted in Diels-Alder, 1,3- rings add Into reaction and Friedel-Craft reactions etc..
The method for the synthesis 2- acyloxy acrylamides reported in document mainly has following several：
(1) Elgomati et al. 1977 report with a kind of raw material of substituted dioxolanes hydrochloric acid effect under Open loop generates corresponding 2- acyloxy acrylamides, but this method raw material is more difficult to prepare that (see reference document： Elgomati, T.et al.Chem.Ber.1977,110,1603).
(2) Yasuhiro et al. reported in 1969 synthesizes corresponding 2- acyls with acryloyl chloride and various substituted amine The method of epoxide acrylamides, but the limitation of substrate is very big, and the reaction time is longer that (see reference document： Yasuhiro, C.et al.Bull.Chem.Soc.Jpn.1969,42,224).
(3) Sodum et al. reported in 1986 with Pyrimdinone raw material and acetic anhydride under conditions of sodium hydroxide it is anti- The method that corresponding 2- acyloxy acrylamides should be generated, but this method for substrate limitation it is larger (see Bibliography：Sodum, R.S.et al.J.Heterocycl.Chem., 1986,23,1239).
(4) Norton et al. reported in 2012 is heated to 40 DEG C of generation phases with isonitrile and carboxylic acid in nitromethane The method for the 2- acyloxy acrylamides answered.But this method can be only generated substituent identical product, product office It is sex-limited that larger (see reference document：Norton, J.R.et al.Tetrahedron.2012,68,10236).
(5) Andrea et al. reported three component reactions under visible light catalytic in 2014, with diazo ketone, (see reference the method for carboxylic acid and isonitrile generation 2- acyloxy acrylamides document：Andream,B.et al.J.Org.Chem.,2014,79,3615)。
In summary, the synthetic method of 2- acyloxy acrylamides has that the above is several, but these reactions Substrate is all relative complex, and limitation is larger, often to react to obtain by several steps, or these reactions need strong acid or highly basic etc. Compare relatively severe condition.
The content of the invention
It is an object of the invention to provide a kind of synthetic method of such compound.
To reach above-mentioned purpose, the reaction mechanism that the inventive method uses for：
R1For phenyl, rubigan, p-methylphenyl, p-methoxyphenyl, an aminomethyl phenyl or o-methoxyphenyl；
R2For methyl or phenyl.
A kind of method for preparing 2- acyloxy acrylamides, it is characterised in that this method has following steps： Under inert atmosphere protection, alkynes, tert-butyl isonitrile, carboxylic acid, palladium, silver oxide and three (o-methyl-phenyl) phosphines are pressed 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) is added in chlorobenzene, Stirring reaction to reaction raw materials disappear at 20 DEG C~80 DEG C；After reaction terminates, washed respectively with water and saturated aqueous common salt, use second Acetoacetic ester extracts product, and organic phase obtains crude product after removing solvent after drying；The crude product obtains corresponding through isolating and purifying Substituted 2- acyloxy acrylamides；Described 2- acyloxy acrylamides structural formulas are：Described alkynes structural formula is：The structural formula of the carboxylic acid is：
The substituted 2- acyloxy acrylamides of the present invention are the intermediates of a kind of important organic reaction, can So that different types of organic chemical reactionses occur.Such as such compound can pass through 1,3- cycloaddition reactions, Friedel- Craft reactions and rearrangement reaction etc. synthesize the compound of a series of complex.Relevant reaction is exemplified below：The third of such 2- acyloxy Rearrangement reaction of the acrylamide compound Jing Guo intramolecular has synthesized a series of pyrroles and the derivative of succimide (sees reference Document:Andrea B.et al.Org.Lett.2009,11,4068).
In addition, the product of the reaction generation alpha-carbonyl acid amides of deacylation base can also occur for such acrylamides (see reference document：Andrea,B.et al.Angew.Chem.Int.Ed.2013,52,2096).
The inventive method raw material is simple and easy to get, and uses conventional reaction dissolvent, simple to operate, mild condition, reaction Environmental protection, when outstanding in yield, there is good development prospect in the industrial production.
Embodiment
Embodiment one：(Z) -3- (tert-butylamino) -1- (4- chlorphenyls) -3- carbonyls propyl- 1- alkene -2- yl acetates
(Z) -3- (tert-butylamino) -1- (4- chlorphenyls) -3- carbonyls propyl- 1- alkene -2- yl acetates use following step： 1. 1 is pressed in 1000 milliliters of reactors：1.5：2.0：0.01：1.5：0.1 mol ratio adds 20.5 grams to chlorobenzene acetylene, and 18.7 Gram tert-butyl isonitrile, 18.0 grams of acetic acid, 0.3 gram of palladium, 52 grams of silver oxides, 4.6 gram of three (o-methyl-phenyl) phosphine, is added 500 milliliters of chlorobenzenes, are heated to 40 DEG C.Tracked and reacted with thin-layer chromatography method, disappeared to reaction raw materials；After 2. reaction terminates, to In system plus water quenching is gone out reaction, and product is extracted with ethyl acetate, and with saturated common salt water washing, is removed after drying with Rotary Evaporators Solvent, obtain crude product；3. crude product column chromatography (petroleum ether:Ethyl acetate=10:1) purify, obtain 32.8 grams of (Z) -3- (uncles Butylamino) -1- (4- chlorphenyls) -3- carbonyl propyl- 1- alkene -2- yl acetates, yield 74%.Fusing point：164℃IR(KBr, cm-1):3352,3060,2981,1767,1629,1538,1456,1364,1360,1196,1105,1010,939,830,753, 668,584,491.
1HNMR(CDCl3,500MHz):δ 7.41 (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).
13CNMR(CDCl3,125MHz):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:calcd for C15H19NO3Cl[M+H]296.1046,found 276.1048.
Embodiment two：(Z) -3- (tert-butylamino) -3- carbonyls -1- (p-methylphenyl) propyl- 1- alkene -2- yl acetates
(Z) -3- (tert-butylamino) -3- carbonyls -1- (p-methylphenyl) propyl- 1- alkene -2- yl acetates use following steps Suddenly：1. 1 is pressed in 1000 milliliters of reactors：4.5：6.0：0.05：3.5：0.2 mol ratio adds 17.4 grams to methylbenzene second Alkynes, 56.1 grams of tert-butyl isonitriles, 54 grams of acetic acid, 1.7 grams of palladiums, 121.7 grams of silver oxides, 9.1 gram of three (o-methyl-phenyl) phosphine, 500 milliliters of chlorobenzenes are added, are heated to 80 DEG C.Tracked and reacted with thin-layer chromatography method, disappeared to reaction raw materials；2. reaction terminates Afterwards, into system plus water quenching is gone out reaction, product is extracted with ethyl acetate, with saturated common salt water washing, rotary evaporation is used after drying Instrument removes solvent, obtains crude product；3. crude product column chromatography (petroleum ether:Ethyl acetate=10:1) purify, obtain 31.8 grams (Z) -3- (tert-butylamino) -3- carbonyls -1- (p-methylphenyl) propyl- 1- alkene -2- yl acetates, yield 77%.Fusing point： 158℃
IR(KBr,cm-1):3324,2966,2924,1769,1633,1540,1447,1366,1310,1193,1009, 937,812.
1HNMR(CDCl3,500MHz):δ 7.37 (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).
13CNMR(CDCl3,125MHz):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:calcd for C16H22NO3[M+H]276.1588,found 276.1594.
Embodiment three：(Z) -3- (tert-butylamino) -1- (4- methoxyphenyls) -3- carbonyls propyl- 1- alkene -2- yl acetates
(Z) -3- (tert-butylamino) -1- (4- methoxyphenyls) -3- carbonyl propyl- 1- alkene -2- yl acetates are using following Step：1. 1 is pressed in 1000 milliliters of reactors：8.0∶4.0：0.03∶5.0：0.3 mol ratio adds 19.8 grams to methoxybenzene Acetylene, 99.7 tert-butyl isonitriles, 36.0 grams of acetic acid, 1.0 grams of palladiums, 173.8 grams of silver oxides, 13.7 gram three (o-methyl-phenyl) Phosphine, 500 milliliters of chlorobenzenes are added, are heated to 50 DEG C.Tracked and reacted with thin-layer chromatography method, disappeared to reaction raw materials；2. react After end, into system plus water quenching is gone out reaction, and product is extracted with ethyl acetate, with saturated common salt water washing, with rotating after drying Evaporimeter removes solvent, obtains crude product；3. crude product column chromatography (petroleum ether:Ethyl acetate=10:1) purify, obtain 32.3 Gram (Z) -3- (tert-butylamino) -1- (4- methoxyphenyls) -3- carbonyl propyl- 1- alkene -2- yl acetates, yield 74%.It is molten Point：110℃.
IR(KBr,cm-1):3397,2972,2931,1752,1675,1643,1603,1518,1453,1367,1296, 1252,1183,1105,1024,831,537.
1HNMR(CDCl3,500MHz):δ 7.43 (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).
13CNMR(CDCl3,125MHz):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:calcd for C16H22NO4[M+H]292.1543,found 292.1537.
Example IV：(Z) -3- (tert-butylamino) -3- carbonyls -1- (aminomethyl phenyl) propyl- 1- alkene -2- yl acetates
(Z) -3- (tert-butylamino) -3- carbonyls -1- (aminomethyl phenyl) propyl- 1- alkene -2- yl acetates use following steps Suddenly：1. 1: 1.0 is pressed in 1000 milliliters of reactors：8.0：0.05：5.0：Methylbenzene second between 0.2 mol ratio adds 17.4 grams Alkynes, 12.5 grams of tert-butyl isonitriles, 72 grams of acetic acid, 1.7 grams of palladiums, 173.8 grams of silver oxides, 9.1 gram of three (o-methyl-phenyl) phosphine, 500 milliliters of chlorobenzenes are added, are heated to 80 DEG C.Tracked and reacted with thin-layer chromatography method, disappeared to reaction raw materials；2. reaction terminates Afterwards, into system plus water quenching is gone out reaction, product is extracted with ethyl acetate, with saturated common salt water washing, rotary evaporation is used after drying Instrument removes solvent, obtains crude product；3. crude product column chromatography (petroleum ether:Ethyl acetate=10:1) purify, obtain 34.7 grams (Z) -3- (tert-butylamino) -3- carbonyls -1- (aminomethyl phenyl) propyl- 1- alkene -2- yl acetates, yield 84%.Fusing point： 119℃。
IR(KBr,cm-1):3316,3059,2967,2920,1766,1634,1541,1479,1442,1364,1312, 1193,1113,1008,907,784,689.
1HNMR(CDCl3,500MHz):δ 7.30 (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).
13CNMR(CDCl3,125MHz):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:calcd for C16H22NO3[M+H]276.1594,found 276.1589.
Embodiment five：(Z) -3- (tert-butylamino) -1- (2- methoxyphenyls) -3- carbonyls propyl- 1- alkene -2- yl acetates
(Z) -3- (tert-butylamino) -1- (2- methoxyphenyls) -3- carbonyl propyl- 1- alkene -2- yl acetates are using following Step：1. 1: 6.0 is pressed in 1000 milliliters of reactors：5.0：Methylbenzene second between 0.01: 4.5: 0.1 mol ratio adds 19.8 grams Alkynes, 74.8 grams of tert-butyl isonitriles, 45.0 grams of acetic acid, 0.3 gram of palladium, 156.4 grams of silver oxides, 4.6 gram three (o-methyl-phenyl) Phosphine, 500 milliliters of chlorobenzenes are added, are heated to 50 DEG C.Tracked and reacted with thin-layer chromatography method, disappeared to reaction raw materials；2. react After end, into system plus water quenching is gone out reaction, and product is extracted with ethyl acetate, with saturated common salt water washing, with rotating after drying Evaporimeter removes solvent, obtains crude product；3. crude product column chromatography (petrol ether/ethyl acetate=10:1) purify, obtain 39.3 Gram (Z) -3- (tert-butylamino) -1- (2- methoxyphenyls) -3- carbonyl propyl- 1- alkene -2- yl acetates, yield 90%.It is molten Point：118℃.
IR(KBr,cm-1):3326,2967,2929,1774,1664,1631,1524,1491,1452,1399,1365, 1295,1254,1180,1106,1018,926,751,668.
1HNMR(CDCl3,500MHz):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).
13CNMR(CDCl3,125MHz):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:calcd for C16H22NO4[M+H]292.1543,found 292.1537.
Embodiment six：(Z) -3- (tert-butylamino) -3- carbonyls -1- phenyl propyl- 1- alkene -2- yl acetates
(Z) -3- (tert-butylamino) -3- carbonyls -1- phenyl propyl- 1- alkene -2- yl acetates use following step：1. 1 is pressed in 1000 milliliters of reactors：2.0：3.0：0.01：2.5：0.1 mol ratio adds 15.3 grams of phenylacetylenes, 25.0 grams of tert-butyl groups Isonitrile, 27.0 grams of acetic acid, 0.3 palladium, 86.9 grams of silver oxides, 4.6 gram of three (o-methyl-phenyl) phosphine, add 500 milliliters of chlorine Benzene, it is heated to 30 DEG C.Tracked and reacted with thin-layer chromatography method, disappeared to reaction raw materials；After 2. reaction terminates, water is added into system Reaction is quenched, product is extracted with ethyl acetate, with saturated common salt water washing, removes solvent with Rotary Evaporators after drying, obtains slightly Product；3. crude product column chromatography (petrol ether/ethyl acetate=10:1) purify, obtain 32.5 grams of (Z) -3- (tert-butyl group ammonia Base) -3- carbonyl -1- phenyl propyl- 1- alkene -2- yl acetates, yield 83%.Fusing point：138℃.
IR(KBr,cm-1):3351,3060,2970,2927,1766,1636,1546,1449,1363,1294,1200, 1113,1041,1008,935,876,766,687,614.
1HNMR(CDCl3,500MHz):δ 7.48 (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).
13CNMR(CDCl3,125MHz):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:calcd for C15H20NO3[M+H]262.1438,found 292.1432.
Embodiment seven：(Z) -3- (tert-butylamino) -3- carbonyls -1- phenyl propyl- 1- alkene -2- yl benzoic acid esters
(Z) -3- (tert-butylamino) -3- carbonyls -1- phenyl propyl- 1- alkene -2- yl benzoic acids esters use following step：1. 1 is pressed in 1000 milliliters of reactors：3.0：4.0：0.05：5.5：0.15 mol ratio adds 15.3 grams of phenylacetylenes, 37.4 grams of tertiary fourths Base isonitrile, 73.3 grams of benzoic acid, 1.7 grams of palladiums, 191.2 grams of silver oxides, 6.8 gram of three (o-methyl-phenyl) phosphine, add 500 Milliliter chlorobenzene, is heated to 80 DEG C.Tracked and reacted with thin-layer chromatography method, disappeared to reaction raw materials；After 2. reaction terminates, to system In plus water quenching go out reaction, product is extracted with ethyl acetate, with saturated common salt water washing, is removed after drying with Rotary Evaporators molten Agent, obtain crude product；3. crude product column chromatography (petrol ether/ethyl acetate=10:1) purify, obtain 39.8 grams of (Z) -3- (tertiary fourths Base amino) -3- carbonyl -1- phenyl propyl- 1- alkene -2- yl benzoic acid esters, yield 82%.Fusing point：148℃.
IR(KBr,cm-1):3428,3324,3067,2970,1743,1637,1546,1452,1314,1251,1119, 1056,1022,910,756,700.
1HNMR(d6-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).
13CNMR(d6-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:calcd for C20H22NO3[M+H]324.1594,found 324.1587.

Claims (1)

1. a kind of preparation method of 2- acyloxy acrylamides, it is characterised in that the structural formula of the compound is：Wherein, R1For chlorphenyl, aminomethyl phenyl, methoxyphenyl or phenyl；R2For methyl or phenyl；
This method has following steps：Under inert atmosphere protection, by alkynes, tert-butyl isonitrile, carboxylic acid, palladium, silver oxide And three (o-methyl-phenyl) phosphine press 1：(1.0~8.0)：(2.0~8.0)：(0.01~0.05)：(1.5~5.0)：(0.1~ 0.3) mol ratio is added in chlorobenzene, and stirring reaction to reaction raw materials disappear at 20 DEG C~80 DEG C；After reaction terminates, water is used Washed respectively with saturated aqueous common salt, product is extracted with ethyl acetate, organic phase obtains crude product after removing solvent after drying；This is thick Product is through isolating and purifying, i.e., the 2- acyloxy acrylamides that are substituted accordingly；Described alkynes structural formula is：The structural formula of the carboxylic acid is：
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