CN102002012A - Method for synthesizing 1,3-oxazole-2,4-diketone compounds - Google Patents

Method for synthesizing 1,3-oxazole-2,4-diketone compounds Download PDF

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CN102002012A
CN102002012A CN 201010548927 CN201010548927A CN102002012A CN 102002012 A CN102002012 A CN 102002012A CN 201010548927 CN201010548927 CN 201010548927 CN 201010548927 A CN201010548927 A CN 201010548927A CN 102002012 A CN102002012 A CN 102002012A
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oxazole
aryl
cyclohexadione compounds
carbonic acid
acid gas
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麻生明
傅春玲
陈国飞
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Zhejiang University ZJU
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Zhejiang University ZJU
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Abstract

The invention discloses a method for synthesizing 1,3-oxazole-2,4-diketone compounds. 3-aryl-2-alkyneamide reacts with carbon dioxide under the action of potassium carbonate or cesium carbonate so as to generate a 1,3-oxazole-2,4-diketone compound. The method is easy to operate, raw materials and reagents are readily available and the reaction has high regioselectivity; the product is easy to separate and purify and has low toxicity, high yield and readily available raw materials; and the method is suitable for synthesizing various substituted 1,3-oxazole-2,4-diketone compounds.

Description

A kind of synthetic 1,3-oxazole-2, the method for 4-cyclohexadione compounds
Technical field
The present invention relates to a kind of synthetic 1,3-oxazole-2, the method for 4-cyclohexadione compounds, promptly by 3-aryl-2-alkynyl amide and carbon dioxide reaction, high regioselectivity ground synthesizes 1,3-oxazole-2,4-cyclohexadione compounds.
Background technology
1,3-oxazole-2,4-cyclohexadione compounds are one of most important intermediates in the organic synthesis, it also is one of modal structural unit in the natural product, have multiple important physical activity, at biological technical field, there is huge value of exploiting and utilizing aspects such as medicine and agricultural chemicals.
In the past synthetic 1,3-oxazole-2, the 4-cyclohexadione compounds generally is that direct heterogeneous ring compound from other is transformed, or alpha-hydroxycarboxylic ester and urea or isocyanate reaction obtain, or Alpha-hydroxy acid amides and chloro-formic ester or carbonate reaction obtain (reference: Chemical Review, 1958,58,63-99; Journal of Medicinal Chemistry, 1991,34,1538-1544; Journal of Medicinal Chemistry, 1994,37,322-328; Journal of Medicinal Chemistry, 2002,45,1518-1534), the toxicity of isocyanic ester or methyl-chloroformate is bigger in the raw material, and the Atom economy of reaction is not high, and general productive rate is not very high.
Summary of the invention
The present invention overcomes the some shortcomings of prior art, has made improvement, and provide a kind of and effectively synthesized 1,3-oxazole-2,4-cyclohexadione compounds method, reaction can be introduced different replacements, and toxicity is low, and productive rate is higher.
Specific embodiments is as follows:
The invention provides a kind of effectively synthetic 1,3-oxazole-2,4-cyclohexadione compounds method, under the effect of salt of wormwood or cesium carbonate, 3-aryl-2-alkynyl amide and carbonic acid gas react, and generate 1,3-oxazole-2, the 4-cyclohexadione compounds, reaction formula is as follows:
Figure 909169DEST_PATH_IMAGE001
Ar is a phenyl, to the propyl group phenyl, and p-methylphenyl, p-methoxyphenyl, to fluorophenyl, 2-thienyl, aryl such as 3-thienyl; R is a benzyl, butyl, and ethyl, allyl group, sec.-propyl, concrete steps are as follows:
(1) in reactor, adds salt of wormwood or cesium carbonate, 3-aryl-2-alkynyl amide and organic solvent dimethyl sulfoxide (DMSO);
(2) conduit that will lead to carbonic acid gas inserts from the reactor mouth, and carbonic acid gas imports in the solution of dimethyl sulfoxide (DMSO) by conduit, and reactor is placed 30 oIn the oil bath of C, stirring reaction 11-16 hour, water cancellation reaction, the extraction that adds diethyl ether, drying;
(3) concentrate, rapid column chromatography obtains 1,3-oxazole-2,4-cyclohexadione compounds.
Organic solvent of the present invention is: dimethyl sulfoxide (DMSO).The concentration of the solution of the organic solvent (dimethyl sulfoxide (DMSO)) of 3-aryl-2-alkynyl amide is 0.1 mol.
Additive of the present invention is a salt of wormwood, cesium carbonate, and the equivalence ratio of additive and 3-aryl-2-alkynyl amide is 3 ~ 2: 1.
Carbonic acid gas of the present invention is a normal pressure.
The present invention has the following advantages: 1) reaction has the regioselectivity of height; 2) can introduce two substituting groups simultaneously; 3) the easily separated purifying of product; 4) toxicity is low, and productive rate is higher, and raw material is easy to get.
Innovative point of the present invention is to have developed a kind of effectively synthetic 1,3-oxazole-2, and the method for 4-cyclohexadione compounds, present method gained corresponding 1,3-oxazole-2, the productive rate of 4-cyclohexadione compounds are 46-72%.
Embodiment
Following example helps to understand the present invention, but is not limited to content of the present invention.
Embodiment 1
In reaction tubes, add salt of wormwood (54.5 mg, 0.39 mmol), take out roasting three times, feed carbon dioxide, add successively after being chilled to room temperature N-benzyl-3-phenyl propine acid amides (46.2 mg, 0.20 mmol) and 2 mL dimethyl sulfoxide (DMSO) stir, and carbonic acid gas imports in the solution of dimethyl sulfoxide (DMSO) by conduit, then reaction tubes is placed 30 oStir after 11 hours in the oil bath of C, take out the conduit of logical carbonic acid gas, add the 10 mL shrends reaction of going out, extracted with diethyl ether (15 mL * 3) merges organic phase, and salt is washed once, anhydrous sodium sulfate drying, concentrated solution, rapid column chromatography (petrol ether/ethyl acetate=20/1), solid product ( Z)- N-benzyl-5-benzene methene base-1,3-oxazole-2,4-diketone 34.0 mg, productive rate 62%, fusing point: 158.2-159.2 oC (normal hexane/methylene dichloride).
1H?NMR?(300?MHz,?CDCl 3)?d?7.79-7.70?(m,?2H),?7.50-7.29?(m,?8H),?6.78?(s,?1H),?4.80?(s,?2H);? 13C?NMR?(75?MHz,?CDCl 3):?d?162.0,?152.0,?137.4,?134.3,?131.1,?130.6,?130.5,?129.0,?128.9,?128.8,?128.5,?113.8,?43.8;?MS?(m/z):?280?(M ++1,?14.65),?279?(M +,?78.90),?118?(100);?IR?(KBr,?cm -1):?1807,?1733,?1674,?1495,?1451,?1433,?1398,?1340,?1309,?1291,?1235,?1170,?1081,?1067;?Anal.?Calcd.?for?C 17H 13NO 3:?C?73.11,?H?4.69,?N?5.02;?Found:?C?73.20,?H?4.72,?N?4.96。
 
Embodiment 2
Press embodiment 1 described method, different is that used substrate and reagent are: N-butyl-3-phenyl propine acid amides (40.1 mg, 0.20 mmol), salt of wormwood (55.8 mg, 0.40 mmol), product ( Z)- N-butyl-5-benzene methene base-1,3-oxazole-2,4-diketone 39.0 mg, productive rate are 80%.Product is a solid, fusing point: 82.7-83.4 oC (normal hexane/methylene dichloride).
1H?NMR?(300?MHz,?CDCl 3)?d?7.80-7.71?(m,?2H),?7.50-7.36?(m,?3H),?6.76?(s,?1H),?3.65?(t,? J?=?7.4?Hz,?2H),?1.78-1.62?(m,?2H),?1.46-1.30?(m,?2H),?0.96?(t,? J?=?7.4?Hz,?3H);? 13C?NMR?(75?MHz,?CDCl 3):?d?162.4,?152.3,?137.5,?131.0,?130.7,?130.4,?129.0,?113.3,?40.0,?29.6,?19.8,?13.5;?MS?(m/z):?246?(M ++1,?4.12),?245?(M +,?25.65),?118?(100);?IR?(KBr,?cm -1):?1816,?1721,?1666,?1495,?1449,?1413,?1354,?1315,?1264,?1236,?1187,?1082,?1006;?Anal.?Calcd.?for?C 14H 15NO 3:?C?68.56,?H?6.16,?N?5.71;?Found:?C?68.88,?H?6.40,?N?5.72。
 
Embodiment 3
Press embodiment 1 described method, different is that used substrate and reagent are: N-ethyl-3-phenyl propine acid amides (34.2 mg, 0.20 mmol), salt of wormwood (55.4 mg, 0.40 mmol), product ( Z)- N-ethyl-5-benzene methene base-1,3-oxazole-2,4-diketone 28.4 mg, productive rate are 66%.Product is a solid, fusing point: 123.6-124.3 oC (normal hexane/methylene dichloride).
1H?NMR?(300?MHz,?CDCl 3)?d?7.85-7.68?(m,?2H),?7.52-7.35?(m,?3H),?6.75?(s,?1H),?3.71?(q,? J?=?7.2?Hz,?2H),?1.32?(t,? J?=?7.2?Hz,?3H);? 13C?NMR?(75?MHz,?CDCl 3):?d?162.1,?152.0,?137.5,?131.0,?130.7,?130.4,?129.0,?113.2,?35.3,?13.0;?MS?(m/z):?218?(M ++1,?5.78),?217?(M +,?43.70),?118?(100);?IR?(KBr,?cm -1):?1813,?1735,?1682,?1496,?1452,?1441,?1415,?1372,?1347,?1320,?1246,?1211,?1169,?1115,?1080,?1045;?Anal.?Calcd.?for?C 12H 11NO 3:?C?66.35,?H?5.10,?N?6.45;?Found:?C?66.31,?H?5.33,?N?6.46。
 
Embodiment 4
Press embodiment 1 described method, different is that used substrate and reagent are: N-allyl group-3-phenyl propine acid amides (36.7 mg, 0.20 mmol), salt of wormwood (56.24 mg, 0.41 mmol), product ( Z)- N-allyl group-5-benzene methene base-1,3-oxazole-2,4-diketone 32.6 mg, productive rate are 72%.Product is a solid, fusing point: 79.7-80.5 oC (normal hexane/methylene dichloride).
1H?NMR?(300?MHz,?CDCl 3)?d?7.84-7.68?(m,?2H),?7.50-7.36?(m,?3H),?6.78?(s,?1H),?6.00-5.78?(m,?1H),?5.45-5.25?(m,?2H),?4.25?(d,? J?=?5.7?Hz,?2H);? 13C?NMR?(75?MHz,?CDCl 3):?d?161.8,?151.8,?137.4,?131.1,?130.6,?130.5,?129.5,?129.0,?119.6,?113.6,?42.2;?MS?(m/z):?230?(M ++1,?6.03),?229?(M +,?41.47),?118?(100);?IR?(KBr,?cm -1):?1816,?1740,?1682,?1452,?1433,?1403,?1351,?1238,?1176,?1101;?Anal.?Calcd.?for?C 13H 11NO 3:?C?68.11,?H?4.84,?N?6.11;?Found:?C?68.47,?H?5.01,?N?5.99。
 
Embodiment 5
Press embodiment 1 described method, different is that used substrate and reagent equivalent are: N-sec.-propyl-3-phenyl propine acid amides (37.6 mg, 0.20 mmol), salt of wormwood (82.9 mg, 0.60 mmol), product ( Z)- N-sec.-propyl-5-benzene methene base-1,3-oxazole-2,4-diketone 31.5 mg, productive rate are 68%.Product is a solid, fusing point: 123.8-125.0 oC (normal hexane/methylene dichloride).
1H?NMR?(300?MHz,?CDCl 3)?d?7.80-7.69?(m,?2H),?7.50-7.36?(m,?3H),?6.72?(s,?1H),?4.44?(heptet,? J?=?7.0?Hz,?1H),?1.49?(d,? J?=?7.0?Hz,?6H);? 13C?NMR?(75?MHz,?CDCl 3):?d?162.2,?151.5,?137.2,?131.0,?130.8,?130.3,?129.0,?112.9,?45.3,?19.4;?MS?(m/z):?232?(M ++1,?5.15),?231?(M +,?34.78),?118?(100);?IR?(KBr,?cm -1):?1815,?1738,?1686,?1666,?1496,?1452,?1403,?1388,?1371,?1347,?1249,?1207,?1181,?1071,?1021,?1002;?Anal.?Calcd.?for?C 13H 13NO 3:?C?67.52,?H?5.67,?N?6.06;?Found:?C?67.48,?H?5.73,?N?6.11。
 
Embodiment 6
Press embodiment 1 described method, different is that used substrate and reagent are: N-sec.-propyl-3-phenyl propine acid amides (37.0 mg, 0.20 mmol), cesium carbonate (132.7 mg, 0.41 mmol), product ( Z)- N-sec.-propyl-5-benzene methene base-1,3-oxazole-2,4-diketone 20.8 mg, productive rate are 46%.Product is a solid.
 
Embodiment 7
Press embodiment 1 described method, different is that used substrate and reagent equivalent are: N-butyl-3-is to propyl group phenyl propiolyl amine (43.3 mg, 0.20 mmol), salt of wormwood (56.6 mg, 0.41 mmol), product ( Z)- N-butyl-5-(p-methylphenyl) methene base-1,3-oxazole-2,4-diketone 35.8 mg, productive rate are 69%.Product is a solid, fusing point: 87.0-88.4 oC (normal hexane/methylene dichloride).
1H?NMR?(300?MHz,?CDCl 3)?d?7.64?(d,? J?=?8.1?Hz,?2H),?7.23?(d,? J?=?8.1?Hz,?2H),?6.73?(s,?1H),?3.64?(t,? J?=?7.4?Hz,?2H),?2.38?(s,?3H),?1.77-1.61?(m,?2H),?1.46-1.25?(m,?2H),?0.95?(t,? J?=?7.2?Hz,?3H);? 13C?NMR?(75?MHz,?CDCl 3):?d?162.4,?152.3,?141.0,?136.9,?131.0,?129.7,?127.9,?113.4,?39.9,?29.6,?21.5,?19.8,?13.5;?MS?(m/z):?260?(M ++1,?4.24),?259?(M +,?25.13),?132?(100);?IR?(KBr,?cm -1):?2959,?2877,?1817,?1735,?1675,?1608,?1514,?1440,?1404,?1362,?1345,?1318,?1288,?1239,?1161,?1094,?1065,?1042;?Anal.?Calcd.?for?C 15H 17NO 3:?C?69.48,?H?6.61,?N?5.40;?Found:?C?69.43,?H?6.66,?N?5.35。
 
Embodiment 8
Press embodiment 1 described method, different is that used substrate and reagent equivalent are: N-butyl-3-p-methylphenyl propine acid amides (48.2 mg, 0.20 mmol), salt of wormwood (56.0 mg, 0.41 mmol), product ( Z)- N-butyl-5-(4 '-propyl group phenyl) methene base-1,3-oxazole-2,4-diketone 39.3 mg, productive rate are 69%.Product is a solid, fusing point: 87.0-88.4 oC (normal hexane/methylene dichloride).
1H?NMR?(300?MHz,?CDCl 3)?d?7.66?(d,? J?=?8.4?Hz,?2H),?7.23?(d,? J?=?8.4?Hz,?2H),?6.74?(s,?1H),?3.64?(t,? J?=?7.4?Hz,?2H),?2.61?(t,? J?=?7.7?Hz,?2H),?1.78-1.57?(m,?4H),?1.46-1.30?(m,?2H),?1.02-0.89?(m,?6H);? 13C?NMR?(75?MHz,?CDCl 3):?d?162.4,?152.3,?145.8,?136.9,?131.1,?129.1,?128.2,?113.5,?40.0,?37.9,?29.6,?24.2,?19.8,?13.7,?13.5;?MS?(m/z):?288?(M ++1,?6.70),?287?(M +,?34.43),?160?(100);?IR?(neat,?cm -1):?2960,?2925,?2873,?1822,?1738,?1674,?1608,?1511,?1442,?1404,?1371,?1345,?1301,?1246,?1192,?1162,?1092,?1042;?HRMS?Calcd?for?C 17H 21NO 3?(M +):?287.1521,?Found:?287.1521。
 
Embodiment 9
Press embodiment 1 described method, different is that used substrate and reagent equivalent are: N-butyl-3-p-methoxyphenyl propine acid amides (45.7 mg, 0.20 mmol), salt of wormwood (55.1 mg, 0.41 mmol), product ( Z)- N-butyl-5-(p-methoxyphenyl) methene base-1,3-oxazole-2,4-diketone 36.7 mg, productive rate are 67%.Product is a solid, fusing point: 106.0-106.6 oC (normal hexane/methylene dichloride).
1H?NMR?(300?MHz,?CDCl 3)?d?7.73-7.65?(m,?2H),?6.98-6.88?(m,?2H),?6.70?(s,?1H),?3.84?(s,?3H),?3.63?(t,? J?=?7.4?Hz,?2H),?1.75-1.61?(m,?2H),?1.45-1.27?(m,?2H),?0.95?(t,? J?=?7.5?Hz,?3H);? 13C?NMR?(75?MHz,?CDCl 3):?d?162.5,?161.3,?152.4,?136.0,?132.9,?123.4,?114.4,?113.3,?55.3,?39.9,?29.6,?19.8,?13.5;?MS?(m/z):?276?(M ++1,?6.32),?275?(M +,?36.31),?148?(100);?IR?(KBr,?cm -1):?2979,?2952,?2867,?2835,?1814,?1740,?1678,?1603,?1514,?1447,?1408,?1345,?1307,?1257,?1163,?1095,?1064,?1027;?Anal.?Calcd.?for?C 15H 17NO 4:?C?65.44,?H?6.22,?N?5.09;?Found:?C?65.38,?H?6.30,?N?5.03。
 
Embodiment 10
Press embodiment 1 described method, different is that used substrate and reagent equivalent are: N-benzyl-3-p-methoxyphenyl propine acid amides (53.3 mg, 0.20 mmol), salt of wormwood (55.6 mg, 0.41 mmol), product ( Z)- N-benzyl-5-(p-methoxyphenyl) methene base-1,3-oxazole-2,4-diketone 42.2 mg, productive rate are 68%.Product is a solid, fusing point: 117.8-118.7 oC (normal hexane/methylene dichloride).
1H?NMR?(300?MHz,?CDCl 3)?d?7.75-7.65?(m,?2H),?7.50-7.40?(m,?2H),?7.40-7.27?(m,?3H),?6.98-6.88?(m,?2H),?6.73?(s,?1H),?4.78?(s,?2H),?3.84?(s,?3H);? 13C?NMR?(75?MHz,?CDCl 3):?d?162.1,?161.3,?152.1,?135.9,?134.5,?133.0,?128.81,?128.77,?128.4,?123.3,?114.5,?113.8,?55.3,?43.6;?MS?(m/z):?310?(M ++1,?13.88),?309?(M +,?68.64),?148?(100);?IR?(KBr,?cm -1):?1805,?1735,?1666,?1601,?1572,?1512,?1455,?1443,?1430,?1401,?1348,?1312,?1259,?1174,?1091,?1070,?1025;?Anal.?Calcd.?for?C 18H 15NO 4:?C?68.89,?H?4.89,?N?4.53;?Found:?C?69.75,?H?5.01,?N?4.64。
 
Embodiment 11
Press embodiment 1 described method, different is that used substrate and reagent equivalent are: N-butyl-3-is to fluorophenyl propine acid amides (43.2 mg, 0.20 mmol), salt of wormwood (56.2 mg, 0.41 mmol), product ( Z)- N-butyl-5-(to fluorophenyl) methene base-1,3-oxazole-2,4-diketone 37.2 mg, productive rate are 72%.Product is a solid, fusing point: 102.6-103.8 oC (normal hexane/methylene dichloride).
1H?NMR?(300?MHz,?CDCl 3)?d?7.81-7.69?(m,?2H),?7.18-7.05?(m,?2H),?6.71?(s,?1H),?3.65?(t,? J?=?7.4?Hz,?2H),?1.78-1.60?(m,?2H),?1.46-1.28?(m,?2H),?0.95?(t,? J?=?7.4?Hz,?3H);? 13C?NMR?(75?MHz,?CDCl 3):?d?163.6?(d,? J?=?251.4?Hz),?162.3,?152.2,?137.2?(d,? J?=?2.7?Hz),?133.1?(d,? J?=?8.4?Hz),?127.0?(d,? J?=?3.2?Hz),?116.2?(d,? J?=?22.7?Hz),?112.0,?40.1,?29.6,?19.8,?13.5?;? 19F?NMR?(282?MHz,?CDCl 3):?d?-108.0?(standard?by?frequency?conversion?of?CDCl 3);?MS?(m/z):?264?(M ++1,?3.56),?263?(M +,?21.57),?136?(100);?IR?(KBr,?cm -1):?2959,?2873,?1819,?1728,?1674,?1602,?1511,?1447,?1416,?1373,?1356,?1310,?1292,?1239,?1186,?1163,?1085,?1058,?1010;?Anal.?Calcd.?for?C 14H 14FNO 3:?C?63.87,?H?5.36,?N?5.32;?Found:?C?63.98,?H?5.41,?N?5.23。
 
Embodiment 12
Press embodiment 1 described method, different is that used substrate and reagent equivalent are: N-benzyl-3-(3 '-thienyl) propine acid amides (47.9 mg, 0.20 mmol), salt of wormwood (55.1 mg, 0.40 mmol), product ( Z)- N-benzyl-5-(3 '-thienyl) methene base-1,3-oxazole-2,4-diketone 34.8 mg, productive rate are 61%.Product is a solid, fusing point: 155.9-156.4 oC (normal hexane/methylene dichloride).
1H?NMR?(300?MHz,?CDCl 3)?d?7.83-7.75?(m,?1H),?7.52-7.41?(m,?3H),?7.40-7.28?(m,?4H),?6.84?(s,?1H),?4.78?(s,?2H);? 13C?NMR?(75?MHz,?CDCl 3):?d?161.9,?151.9,?136.6,?134.4,?132.0,?130.7,?128.9,?128.8,?128.6,?128.5,?126.7,?107.8,?43.8;?MS?(m/z):?286?(M ++1,?16.21),?285?(M +,?100);?IR?(KBr,?cm -1):?3102,?3031,?2947,?1808,?1735,?1674,?1518,?1495,?1456,?1438,?1406,?1354,?1343,?1322,?1249,?1212,?1156,?1090,?1069;?Anal.?Calcd.?for?C 15H 11NO 3S:?C?63.14,?H?3.89,?N?4.91;?Found:?C?63.18,?H?4.09,?N?4.99。
 
Embodiment 13
Press embodiment 1 described method, different is that used substrate and reagent equivalent are: N-benzyl-3-(2 '-thienyl) propine acid amides (47.1 mg, 0.20 mmol), salt of wormwood (81.6 mg, 0.59 mmol), product ( Z)- N-benzyl-5-(2 '-thienyl) methene base-1,3-oxazole-2,4-diketone 30.7 mg, productive rate are 55%.Product is a solid, fusing point: 177.2-178.0 oC (normal hexane/methylene dichloride).
1H?NMR?(300?MHz,?CDCl 3)?d?7.59?(d,? J?=?4.8?Hz,?1H),?7.53-7.40?(m,?3H),?7.40-7.28?(m,?3H),?7.12?(t,? J?=?4.4?Hz,?1H),?7.01?(s,?1H),?4.78?(s,?2H);? 13C?NMR?(75?MHz,?CDCl 3):?d?161.5,?151.6,?135.6,?134.4,?133.5,?133.1,?132.0,?128.9,?128.8,?128.5,?128.1,?107.4,?43.8;?MS?(m/z):?286?(M ++1,?13.07),?285?(M +,?74.61),?124?(100);?IR?(KBr,?cm -1):?3104,?1810,?1728,?1668,?1495,?1457,?1435,?1398,?1344,?1318,?1247,?1231,?1167,?1071,?1051;?Anal.?Calcd.?for?C 15H 11NO 3S:?C?63.14,?H?3.89,?N?4.91;?Found:?C?63.11,?H?3.97,?N?5.01。

Claims (4)

1. one kind is synthesized 1,3-oxazole-2, and the method for 4-cyclohexadione compounds is characterized in that under the effect of salt of wormwood or cesium carbonate 3-aryl-2-alkynyl amide and carbonic acid gas react, and generates 1,3-oxazole-2, the 4-cyclohexadione compounds, reaction formula is as follows:
Figure 523434DEST_PATH_IMAGE002
Ar is a phenyl, to the propyl group phenyl, and p-methylphenyl, p-methoxyphenyl, to fluorophenyl, 2-thienyl, aryl such as 3-thienyl; R is a benzyl, butyl, and ethyl, allyl group, sec.-propyl, its concrete steps are as follows:
(1) in reactor, adds salt of wormwood or cesium carbonate, 3-aryl-2-alkynyl amide and organic solvent dimethyl sulfoxide (DMSO);
(2) conduit that will lead to carbonic acid gas inserts from the reactor mouth, and carbonic acid gas imports in the solution of dimethyl sulfoxide (DMSO) by conduit, and reactor is placed 30 oIn the oil bath of C, stirring reaction 11-16 hour, water cancellation reaction, the extraction that adds diethyl ether, drying;
(3) concentrate, rapid column chromatography obtains 1,3-oxazole-2,4-cyclohexadione compounds.
2. according to claim 1 synthetic 1,3-oxazole-2, the method for 4-cyclohexadione compounds is characterized in that the concentration of solution of the organic solvent (dimethyl sulfoxide (DMSO)) of described 3-aryl-2-alkynyl amide is 0.1 mol.
3. according to claim 1 synthetic 1,3-oxazole-2, the method for 4-cyclohexadione compounds, the equivalence ratio that it is characterized in that described additive and 3-aryl-2-alkynyl amide is 3 ~ 2: 1.
4. according to claim 1 synthetic 1,3-oxazole-2, the method for 4-cyclohexadione compounds, the pressure that it is characterized in that carbonic acid gas is normal pressure.
CN 201010548927 2010-11-18 2010-11-18 Method for synthesizing 1,3-oxazole-2,4-diketone compounds Pending CN102002012A (en)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106518798A (en) * 2016-10-10 2017-03-22 河南师范大学 Method for synthesizing 2-oxazolidinone compound by catalyzing CO2 through hydramine
CN109180601A (en) * 2018-09-27 2019-01-11 大连理工大学 A kind of organic amine catalysis CO2The method for synthesizing 2,4- oxazolidinedione class compound
CN110590691A (en) * 2019-10-12 2019-12-20 常州大学 Method for preparing tetra-substituted vinyl oxazolidine-2, 4-diketone from carbon dioxide
CN113603653A (en) * 2021-08-23 2021-11-05 南通大学 Synthesis method of visible light-promoted selenooxazolidine-2.4-dione

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
《Org. Biomol. Chem.》 20101117 Guofei Chen et al. A novel synthesis of oxazolidine-2,4-diones via an efficient fixation of CO2 with 3-aryl-2-alkynamides 105-110 1-4 第9卷, 第1期 2 *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106518798A (en) * 2016-10-10 2017-03-22 河南师范大学 Method for synthesizing 2-oxazolidinone compound by catalyzing CO2 through hydramine
CN106518798B (en) * 2016-10-10 2018-08-21 河南师范大学 It is a kind of to be catalyzed CO using hydramine2The method for synthesizing 2- Oxazolidinone derivatives
CN109180601A (en) * 2018-09-27 2019-01-11 大连理工大学 A kind of organic amine catalysis CO2The method for synthesizing 2,4- oxazolidinedione class compound
CN110590691A (en) * 2019-10-12 2019-12-20 常州大学 Method for preparing tetra-substituted vinyl oxazolidine-2, 4-diketone from carbon dioxide
CN113603653A (en) * 2021-08-23 2021-11-05 南通大学 Synthesis method of visible light-promoted selenooxazolidine-2.4-dione
CN113603653B (en) * 2021-08-23 2022-05-13 南通大学 Synthesis method of selenooxazolidine-2, 4-dione promoted by visible light

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