2h-chromene derivatives as analgesic agents
Compound 1a and its derivatives prepared by using microwave irradiation in modified montmorillonite Н-K10 clay have solved the problems of low activity and toxicity of existing analgesic drugs and achieved effective analgesic effects and new types of low toxicity. Analgesics.
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example 1
[0039] Example 1: Synthesis of Compound 1a (4,7-dimethyl-2-(thiophen-2-yl)octahydro-2H-chromen-4-ol)
[0040]
[0041] 0.29g thiophene-2-carbaldehyde and 3ml CH 2 Cl 2 The solution made by adding 1.3g К10 clay and 5ml CH 2 Cl 2 The resulting suspension was then added by adding 0.400 g of isopulegol 2 and 3 ml of CH 2 Cl 2 made solution. The solvent was evaporated and the reaction mixture was kept at room temperature for 60 minutes. Then 10 ml of EtOAc was added, the catalyst was filtered and the solvent was evaporated. The resulting mixture was separated on a 13 g silica gel column (eluent: hexane solution with ethyl acetate content ranging from 0 to 100%). The reaction yielded 0.543 g of compound 1a (yield 78%). The hydrogen nuclear magnetic resonance spectrum (NMR of compound 1a 1 H) Consistent with the spectrum published in literature [4].
example 2
[0042] Example 2: Synthesis of Compound 1b (4,7-dimethyl-2-(3-methylthiophen-2-yl) octahydro-2H-chromen-4-ol)
[0043]
[0044] Similar to Example 1, in the presence of 1.1g К10 clay, the interaction of 0.300g isopulegol 2 and 0.25g 3-methylthiophene-2-carbaldehyde for 120 minutes can obtain 0.381g of compound 1b (yield 70 %).
[0045] Proton nuclear magnetic resonance spectrum (NMR 1 H)(CDCl 3 ):0.88-0.97(m,1H,H a -8); 0.92(d,J(16,9a)=6.6Hz,3H,H-16); 1.03(dddd,J(7a,7e)=J(7a,8a)=12.8Hz,J(7a, 6a)=12.1Hz, J(7a,8e)=3.3Hz, 1H,H a -7); 1.11(ddd,J(10a,10e)=J(10a,9a)=12.2Hz,J(10a,1a)=10.8Hz,1H,H a -10); 1.28(d,J(15,4a)=0.7Hz,3H,H-15); 1.31(ddd,J(6a,7a)=12.1Hz,J(6a,1a)=10.2Hz,J (6a,7e)=3.3Hz,1H,H a -6); 1.40-1.53(m,2H,H a -9,OH); 1.72(ddddd, J(8e,8a)=12.9Hz, J(8e,7a)=J(8e,9a)=J(8e,7e)=3.3Hz, J(8e,10e) =2.0Hz,1H,He -8); 1.85(ddq, J(4a,4e)=12.7Hz, J(4a,3a)=11.7Hz, J(4a,15)=0.7Hz,1H,H a -4); 1.91-1.97(m,1H,H e -7); 1.95(dd,J(4e,4a)=12.7Hz,J(4e,3a)=2.4Hz,1H,H e -4); 1.99(dm...
example 3
[0046] Example 3: Synthesis of compound 1c (4,7-dimethyl-2-(5-methylthien-2-yl)octahydro-2H-chromen-4-ol).
[0047]
[0048] Similar to Example 1, in the presence of 1.1g K10 clay, the interaction of 0.300g isopulegol 2 and 0.25g 5-methylthiophene-2-carbaldehyde produced 0.386g compound 1c (yield 71% ).
[0049] Proton nuclear magnetic resonance spectrum (NMR 1 H)(CDCl 3 ):0.87-0.96(m,1H,H a -8); 0.92(d,J(16,9a)=6.6Hz,3H,H-16); 1.02(dddd,J(7a,7e)=J(7a,8a)=12.8Hz,J(7a, 6a)=12.2Hz, J(7a,8e)=3.3Hz, 1H,H a -7); 1.09(ddd,J(10a,10e)=J(10a,9a)=12.3Hz,J(10a,1a)=10.8Hz,1H,H a -10); 1.25(d,J(15,4a)=0.8Hz,3H,H-15); 1.28(ddd,J(6a,7a)=12.2Hz,J(6a,1a)=10.2Hz,J (6a,7e)=3.3Hz,1H,H a -6); 1.39-1.52(m,2H,H a -9,OH); 1.72(ddddd, J(8e,8a)=12.8Hz, J(8e,7a)=J(8e,9a)=J(8e,7e)=3.3Hz, J(8e,10e) =2.0Hz,1H,H e -8); 1.86(ddq, J(4a,4e)=12.7Hz, J(4a,3a)=11.7Hz, J(4a,15)=0.8Hz,1H,H a -4); 1.93(dddd, J(7e,7a)=12.8Hz, J(7e,6a)=J(7e,8a)=J(7e,8e)=3.3Hz,1H,H e -7); 1.99(dm,J(10e,10a)=12.3Hz,1H,H ...
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