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4-(substituted phenyl)-6-ferrocenyl-3,4-dihydropyrimidine-2(1H)-one and preparation method thereof

A technology of ferrocenyl and dihydropyrimidine, which is applied in the field of chemical synthesis and can solve the problem that substituents have no obvious influence on compound synthesis

Active Publication Date: 2018-06-22
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The 4 and 6 substituents in the synthesis of 3,4-dihydropyrimidin-2(1H)-one derivatives at home and abroad are mainly concentrated in small substituents, such as methyl, ethyl, phenyl, etc. The synthetic effect of the compound is not obvious

Method used

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  • 4-(substituted phenyl)-6-ferrocenyl-3,4-dihydropyrimidine-2(1H)-one and preparation method thereof
  • 4-(substituted phenyl)-6-ferrocenyl-3,4-dihydropyrimidine-2(1H)-one and preparation method thereof
  • 4-(substituted phenyl)-6-ferrocenyl-3,4-dihydropyrimidine-2(1H)-one and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] 1) Add 0.2281g (1mmol) acetyl ferrocene, 0.0721g (1.2mmol) urea, 0.1273g (1.2mmol) benzaldehyde, 0.0200g (0.74mmol) boric acid and 10mL acetic acid to a three-necked flask, and react at 100°C to The starting material reacted completely (reaction monitored by TLC) for 1 h.

[0042] 2) Pour the reaction mixture into water to precipitate solids, suction filter, wash with water, dry naturally, and recrystallize through absolute ethanol to obtain 4-phenyl-6-ferrocenyl-3,4-dihydropyrimidine- 2(1H)-one.

[0043] Yield: 86%; m.p.: 173-175℃; IR (KBr, v / cm -1 ):3443,3303υ(N-H),3187υ(C=C-H),2925υ(-CH-),1699υ(-C=O),1590,1543υ(-C=C,Ar),1268υ(C-N),1198υ( C-C),1101υ as (C-C,Fc),1028γ(C-H,Fc),746,696γ(C-H,Ar-R);

[0044] 1 H NMR (400MHz, CDCl3) δ9.37(s,1H,N-H),7.59(d,1H,Ar-H),7.41(m,1.5Hz,2H,Ar-H),7.29(d,2H,Ar-H) -H), 6.86(d, 1H, C=C-H), 6.12(s, 1H, -CH-), 5.63-4.86(m, 4H, Fc-H).

Embodiment 2

[0046] 1) Add 0.2281g (1mmol) acetyl ferrocene, 0.0721g (1.2mmol) urea, 0.1442g (1.2mmol) p-tolualdehyde, 0.0200g (0.74mmol) boric acid and 10mL acetic acid to the three-necked flask, 100 The reaction was carried out at ℃ until the raw materials were completely reacted (monitored by TLC), and the time was 1 h.

[0047]2) Pour the reaction mixture into water to precipitate a solid, suction filter, wash with water, dry naturally, and recrystallize through absolute ethanol to obtain 4-(4-methylphenyl)-6-ferrocenyl-3, 4-Dihydropyrimidin-2(1H)-one.

[0048] Yield: 86.3%; m.p.: 133-136℃; IR (KBr, v / cm -1 ):3441,3298,3275(N-H),3200,3104,3033(C=C-H),2924υ(-CH-),2854υ(-CH 3 ), 1680υ(-C=O), 1597,1537,1461υ(-C=C, Ar), 1383δs(-CH 3 ),1271υ(C-N),1199υ(C-C),1100υ as (C-C,Fc),1050,1015γ(C-H,Fc),843,805γ(C-H,Ar-R);

[0049] 1 H NMR (400MHz, CDCl3) δ9.35(s,1H,N-H),7.58(d,1H,Ar-H),7.29(d,2H,Ar-H),7.09(d,1H Ar-H), 6.84(d,1H,C=C-H),6.07(s,1H,-CH-),5.60-5.05(m,4H,Fc-H),2.28(s,3H,-CH 3 ). ...

Embodiment 3

[0051] 1) Add 0.2281g (1mmol) acetyl ferrocene, 0.0721g (1.2mmol) urea, 0.1634g (1.2mmol) p-methoxybenzaldehyde, 0.0200g (0.74mmol) boric acid and 10mL acetic acid to the three-necked flask, The reaction was carried out at 100° C. until the raw materials were completely reacted (reaction monitored by TLC), and the time was 1 h.

[0052] 2) Pour the reaction mixture into water to precipitate solids, filter with suction, wash with water, dry naturally, and recrystallize through absolute ethanol to obtain 4-(4-methoxyphenyl)-6-ferrocenyl-3 , 4-Dihydropyrimidin-2(1H)-one.

[0053] Yield: 87%; m.p.: 129-131℃; IR (KBr, v / cm -1 ):3443,3302υ(N-H),3191,3007υ(C=C-H),2924υ(-CH-),2854υ(-CH 3 ), 1694υ(-C=O), 1669υ(-C=C), 1593,1540,1513, 1461υ(-C=C, Ar), 1373δs(-CH 3 ),1250υ(C-N),1193υ(C-C),1101υ as (C-C, Fc), 1027γ (C-H, Fc), 821γ (C-H, Ar-R);

[0054] 1 H NMR(400MHz, CDCl3)δ9.35(s,1H,N-H),7.55(d,1H,Ar-H),7.33(d,2H,Ar-H),6.84(d,1H,Ar-H) ,6.80(d,1H,C=C-H),6.06(s,1H,-CH-),5.56-5.17(m,...

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Abstract

The invention discloses 4-(substituted phenyl)-6-ferrocenyl-3,4-dihydropyrimidine-2(1H)-one and a preparation method thereof. The method comprises the following steps: adding A (mmol acetylferrocene),B (mmol nitrogen source), C (mmol aromatic aldehyde), D (mmol boracic acid) and E (mL acetic acid) into a three-necked flask, wherein a ratio of A to B to C to D is 1 to (1.1 to 1.2) to (1.1 to 1.2)to 0.74, and a ratio of A to E is 1 to (9 to 12); performing reaction at 100 DEG C until the raw materials are completely subjected to reaction; pouring a reaction mixed solution into water and separating solids out; performing suction filtration and water washing on the solids; naturally airing the solids; performing recrystallization through absolute ethyl alcohol to obtain a 4-(substituted phenyl)-6-ferrocenyl-3,4-dihydropyrimidine-2(1H)-one pure product. The invention discloses a series of novel unreported compounds and the preparation method thereof.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and particularly relates to 4-(substituted phenyl)-6-ferrocenyl-3,4-dihydropyrimidin-2(1H)-one and a preparation method thereof. Background technique [0002] 3,4-Dihydropyrimidin-2(1H)-one derivatives are a class of nitrogen-containing heterocyclic compounds with important biological activities. It has been found through research that they have potentials such as biology and pharmacology, and are important drug intermediates. 3,4-dihydropyrimidin-2(1H)-one derivatives have calcium antagonism, antihypertensive, anticancer and other pharmaceutical activities, and can be used as calcium channel agents, antiallergic agents, antihypertensive agents, antagonists, and can also be used as As a lead in the development of anticancer drugs, in addition, alkaloids with a guanidine structure isolated from marine organisms, containing the core of dihydropyrimidinone, have significant biological activities, s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F17/02A61P31/04
CPCC07F17/02
Inventor 刘玉婷杨晓明尹大伟王忠宇杨丽莎刘凯李乐园
Owner SHAANXI UNIV OF SCI & TECH
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