Method for synthesizing optically-active 2,3-dihydro quinazolinone derivative by using chiral spiro phosphoric acid as catalyst
A technology catalyzed by dihydroquinazolinone and spirocyclic phosphoric acid, which is applied in organic chemistry and other fields, can solve the problems of low reaction yield, poor enantioselectivity, and lack of atom economy, and achieve mild reaction conditions and high The effect of optical activity
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Embodiment 1
[0018] Add anthranilamide compound (0.05mmol), benzaldehyde (0.055mmol) containing a substituent in the ortho position, (S)-spirocyclic phosphoric acid (0.005mmol) of structural formula (1) in the reaction flask, Molecular sieves (75 mg), inject 1 mL of chloroform, and react at room temperature for 24 hours. After the reaction is completed, directly use silica gel column chromatography, and the eluent is ethyl acetate / petroleum ether=1:2 to obtain the corresponding optically active 2,3- Dihydroquinazolin-4(1H)-one derivatives; and product characterization. In this example, "anthranilamide compound" is anthranilamide, and "benzaldehyde containing a substituent at the ortho position" is o-bromobenzaldehyde. (S)-2-(2-Bromophenyl)-2,3-dihydroquinazolin-4(1H)-one
[0019]
[0020] White solid;m.p.176-178℃;99%yield;98%ee,determined by HPLC[Daicel Chiralpak AD-H,n-hexane / i-propanol=80 / 20,1.0mL / min,λ=254nm,t( major)=15.479min,t(minor)=23.275min].[α] D 20 =+151.2°(c=1.0,THF); ...
Embodiment 2
[0022] The steps are the same as in Example 1. In this example, the "anthranilamide compound" is anthranilamide, and the "benzaldehyde containing a substituent in the ortho position" is o-nitrobenzaldehyde.
[0023] (S)-2-(2-nitrophenyl)-2,3-dihydroquinazolin-4(1H)-one
[0024]
[0025] Yellow solid;m.p.192-193℃;99%yield;95%ee,determined by HPLC[Daicel Chiralpak AS-H,n-hexane / i-propanol=50 / 50,0.7mL / min,λ=254nm,t( minor)=26.489min,t(major)=40.962min].[α] D 20 =+195.2°(c=0.75,THF); 1 H NMR (400MHz, DMSO-d 6 )δ6.34(s,1H),6.72(t,J=8.0Hz,1H),6.77(d,J=8.0Hz,1H),7.01(s,1H),7.24-7.28(m,1H), 7.61-7.67(m,2H),7.77-7.81(m,1H),7.86(dd,J 1 =8.0Hz,J 2 =1.2Hz,1H),8.07(dd,J 1 =8.4Hz,J 2 =1.2Hz,1H),8.22(s,1H); 13 C NMR (100MHz, DMSO-d 6 )δ62.6, 115.0, 115.4, 118.1, 125.2, 127.8, 129.4, 130.3, 134.0, 134.4, 136.4, 147.6, 148.1, 163.8; IR (KBr, cm -1 )3422,3188,3061,2934,1670,1612,1514,1342,1152,855,742,697;HRMS(EI-TOF):calcd for C 14 h 11 N 3 o 3 269.0800,found269.0802.
Embodiment 3
[0027]The steps are the same as in Example 1. In this example, the "anthranilamide compound" is anthranilamide, and the "benzaldehyde containing a substituent in the ortho position" is o-chlorobenzaldehyde.
[0028] (S)-2-(2-Chlorophenyl)-2,3-dihydroquinazolin-4(1H)-one
[0029]
[0030] White solid;m.p.208-210℃;99%yield;98%ee,determined by HPLC[Daicel Chiralcel OD-H,n-hexane / i-propanol=80 / 20,1.0mL / min,λ=254nm,t( major)=13.066min,t(minor)=16.992min].[α] D 20 =+172.6°(c=0.82,THF); 1 H NMR (400MHz, DMSO-d 6 )δ6.15(s,1H),6.70-6.78(m,2H),7.02(s,1H),7.24-7.28(m,1H),7.38-7.42(m,2H),7.48-7.51(m, 1H),7.66-7.69(m,2H),8.22(s,1H); 13 C NMR (100MHz, DMSO-d 6 )δ64.2, 115.0, 115.2, 117.9, 127.8, 127.9, 129.2, 130.1, 130.8, 132.3, 133.9, 138.4, 148.1, 164.1; IR (KBr, cm -1 ) 3361, 3197, 3065, 1647, 1614, 1502, 1390, 1256, 1188, 1051, 739, 539; HRMS (EI-TOF): calcd for C 14 h 11 ClN 2 O258.0560,found258.0567.
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