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  3. An efficient method for the synthesis of pyrido[3,2-d]pyrimidine derivatives

An efficient method for the synthesis of pyrido[3,2-d]pyrimidine derivatives

Number of pages: 109 File Format: word File Code: 31878
Year: 2014 University Degree: Master's degree Category: Chemical - Petrochemical Engineering
Tags/Keywords: 6- Aminouracil - Benzyl acetonitrile - Catalyst - MCR - Multicomponent reactions - Nano catalyst - pyrimidine - Pyrite derivatives
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  • Summary of An efficient method for the synthesis of pyrido[3,2-d]pyrimidine derivatives

    Master's Thesis

    Department of Chemistry, Department of Organic Chemistry

    Abstract

    An efficient method for the synthesis of pyrido[3,2-d]pyrimidine derivatives

    From Three-component condensation of 6-aminouracil, 6-amino2-thiouracil or 6-amino-1,3-dimethyluracil with aryl aldehydes and malononitrile, a class of pyrido[3,2-d]pyrimidine derivatives in the presence of high-performance basic catalysts, was prepared in water as a green solvent under reflux conditions.

    Keywords: Amiouracils, pyrido[3,2-d]pyrimidines, basic catalyst, multicomponent reaction

    1 Multicomponent reactions [1]

    Multicomponent reactions are considered a promising and fundamental field in organic chemistry. Multicomponent reactions (MCR) are a process in which three or more components are combined and a product with the properties of all the components is synthesized. One of the characteristics of these reactions is the possibility of producing various products with different molecular structures in a short period of time. Also, the most important criterion for the efficiency and capabilities of these reactions is to minimize the number of reaction purification steps as much as possible [1].

    1-2 pyridopyrimidines

    The construction of new compounds containing pyridine in the chemistry of heteroaromatics [2] and the investigation of their biological effects have a special place and this The structural skeleton is present in many medicinal and natural compounds. Pyridopyrimidines are one of the famous structures in drug design. Figure 1-1 shows the structure of some pyridopyrimidines]2,3[.

     

     

    An example of the application of MCR in pharmaceuticals is the synthesis of a family of heterocyclic compounds. Heterocyclic compounds play a key role in the synthesis of various drugs. Synthesis of boiled pyridine and pyrimidine heterocycles

    due to its increasing importance in medicinal chemistry as anticancer[3], antiviral2, antibacterial3, antifungal4, antihypertensive5 and antihepatitis6 has attracted a lot of attention. Figure 2-1 shows the structure of some bioactive pyrido[3,2-d]pyrimidine derivatives [4,5]. Pyrido[3,2-d]pyrimidines in aqueous medium without catalyst:

    One ??of the principles of green chemistry is to use safe solvents in chemical reactions. The advantages of water are non-toxic, cheap and availability, non-corrosive, non-flammable and known as a green solvent. In a report during a two-component reaction in aqueous medium, from the reaction of aminouracil derivative 9 with diethyl 2-ethoxymaleate (10), pyrido[3,2-d]pyrimidine derivatives 11 were synthesized (Scheme 1-1) [6,7].

    Scheme 1-1 Preparation of pyrido[3,2-d]pyrimidine derivatives in aqueous medium and without catalyst

    Rahmati and his colleagues synthesized pyrido[3,2-d]pyrimidine derivatives 14 (Scheme 1-2) [8] in a three-component reaction from benzyl acetonitrile (12), aromatic aldehydes and aminouracil 13 (Scheme 1-2).

    For synthesis Pyrido[3,2-d]pyrimidine derivatives 16 with high yield were used from the three-component reaction of 6-amino-2-mercaptopyrimidin-4-ol (15), malononitrile and aromatic aldehydes with sodium lauryl sulfate catalyst in aqueous medium (Scheme 1-3) [9].

    Scheme 1-3 Preparation of derivatives Pyrido[3,2-d]pyrimidine in aqueous medium with sodium lauryl sulfate catalyst

     

    1-2-1-2 Synthesis of pyrido[3,2-d]pyrimidines under classical conditions using ZrO2 nanocatalyst

    The desire to reduce the harmful effects of chemicals drives us towards green chemistry which leads to the design of new reactions with the production of safe products and the reduction of material and energy consumption.Part of this goal is provided by using environmentally friendly catalysts such as nano ZrO2. In this report, for the synthesis of pyrido[3,2-d]pyrimidine derivatives 19, the reaction of methyl cyanoacetate (17), amino uracil 18 and aromatic aldehydes in the vicinity of ZrO2 nano catalyst and solvent-free conditions were used. Among the advantages of the above method, it can be mentioned that it is compatible with the environment, speeding up the reaction time and increasing the efficiency (Scheme 1-4) [10].

    Scheme 1-4 Using zirconium oxide nanoparticles in the synthesis of pyrido[3,2-d]pyrimidine derivatives

    1-2-1-3 synthesis of pyrido[3,2-d]pyrimidines under classical conditions using Fe3O4 nanocatalyst

    In recent years, the use of metal oxide nanoparticles as catalysts in various scientific fields has increased due to the significant increase in reaction speed, the reusability of the catalyst, and its good compatibility with the environment. Dr. Mamqani and his colleagues synthesized derivatives 21 from the reaction of 3-(amino-4-oxo-2-thiooxo-4,3,2,1-tetrahydropyrimidin-5-yl)-3-oxopropanenitrile (20) with various aldehydes in dimethylformamide solvent and at a temperature of 120 oC (Shemai 1-5) [11].

    Shemai 1-5 Use of nano Fe3O4 catalyst in the synthesis of pyrido[3,2-d]pyrimidine derivatives From the catalyst of triethylbenzylammonium chloride (TEBAC)

    From the one-pot and three-component reaction of aromatic aldehydes, 6,2-diaminopyrimidine-4-(H3)-one (22) and Meldermic acid (23) in water solvent and with the catalyst of triethylbenzylammonium chloride (TEBAC), derivatives 2-amino-5-aryl-6,5-dihydropyrido[3,2-d]pyrimidine-7,4(H3,H8)-dione (24) were synthesized with high yield (Scheme 1-6)]12[.

    Scheme 1-6 Using triethylbenzylammonium chloride (TEBAC) in the synthesis of derivatives Pyrido[3,2-d]pyrimidine

    The proposed mechanism for the synthesis of the above derivatives is that, firstly, intermediate 25 is obtained from Novenagle condensation between aldehyde and Melderm acid. Further, the addition of 6,2-diaminopyrimidine 22 to this intermediate and then cyclization produces compound 26, which finally produces derivatives by removing one molecule of carbon dioxide and acetone. It produces pyrido[3,2-d]pyrimidine 24 (Scheme 1-7).

    Scheme 1-7 Synthesis mechanism of pyrido[3,2-d]pyrimidines using triethylbenzylammonium chloride (TEBAC)

    1-2-1-5 Synthesis of pyrido[3,2-d]pyrimidine derivatives Using chalcone[4]

    Cairuga[5] and his colleagues from the three-component reaction of 6-aminothiouracil (27) and saturated aromatic ketone-?,?28 in dimethylformamide solvent produced derivatives 29 (Shammai 1-8) [13].

    Shammai 1-8 Synthesis of derivatives Pyrido[3,2-d]pyrimidine using chalcone

     

    1-2-1-6 Synthesis of pyrido[3,2-d]pyrimidine derivatives using 4-amino-6,2-dihydroxypyridine

    Wang[6] and coworkers, from one-pot reaction Methylcyanoacetate (17) and 4-amino-2,6-dihydroxypyridine (30) in ethanol solvent and potassium fluoride-alumina catalyst prepared pyrido[3,2-d]pyrimidine derivatives 31 (Shemai 1-9) [14]. Using potassium fluoride-alumina catalyst

    1-2-1-7 Synthesis of pyrido[3,2-d]pyrimidine derivatives using arylidene malononitrile

    Gazar[7] and his colleagues New medicinal compounds of pyrido[3,2-d]pyrimidine 34 synthesized from the reaction of arylidene malononitrile derivatives 32 and 6-aminothiouracil 27 with dimethylformamide solvent (Scheme 1-10) [15].

  • Contents & References of An efficient method for the synthesis of pyrido[3,2-d]pyrimidine derivatives

    List:

    Abstract 1

    1-1 multicomponent reactions. 3

    1-2 pyridopyrimidines 3

    1-2-1 synthesis of pyrido[3,2-d]pyrimidines 5

    1-2-1-1 synthesis of pyrido[3,2-d]pyrimidines in aqueous environment without catalyst: 5

    1-2-1-2 Synthesis of pyrido[3,2-d]pyrimidines under classical conditions using nanocatalyst ZrO2 6

    1-2-1-3 Synthesis of pyrido[3,2-d]pyrimidines under classical conditions using nanocatalyst Fe3O4 7

    1-2-1-4 Synthesis of pyrido[3,2-d]pyrimidines under classical conditions using triethylbenzylammonium chloride (TEBAC) catalysis 7

    1-2-1-5 Synthesis of pyrido[3,2-d]pyrimidine derivatives using chalcone. 9

    1-2-1-6 synthesis of pyrido[3,2-d]pyrimidine derivatives using 4-amino-6,2-dihydroxylpyridine. 9

    1-2-1-7 synthesis of pyrido[3,2-d]pyrimidine derivatives using arylidene malononitrile. 10

    1-2-1-8 synthesis of pyrido[3,2-d]pyrimidine derivatives using 6-aminouracil. 10

    1-2-1-9 preparation of pyrido[3,2-d]pyrimidine derivatives using Diels-Alder reaction 11

    1-2-1-10 preparation of pyrido[3,2-d]pyrimidine derivatives using palladium-statopotassium carbonate catalyst. 12

    1-2-1-11 Preparation of pyrido[3,2-d]pyrimidine derivatives using barbituric acid. 13

    1-2-1-12 Preparation of pyrido[3,2-d]pyrimidine derivatives using isatin. 14

    1-2-1-13 Preparation of pyrido[3,2-d]pyrimidine derivatives using gravitamine B1 catalysis 15

    1-2-1-14 Preparation of pyrido[3,2-d]pyrimidine derivatives using 2-amino-6-phenyl-4-(trifluoromethyl)nicotinonitrile 16

    1-2-1-15 Preparation of pyrido[3,2-d]pyrimidine derivatives using hydrochloric acid catalyst. 17

    1-2-1-16 preparation of pyrazolo]'3,'4:6,5[pyrido]3,2-[dpyrimidine derivatives using thiobarbituric acid. 17

    1-2-1-17 Preparation of pyrido[3,2-d]pyrimidine derivatives using the catalysis of dimethyl chloride. 18

    1-2-1-18 preparation of pyrido[3,2-d]pyrimidine derivatives catalyzed by para-toluenesulfonic acid. 19

    1-2-1-19 Preparation of pyrido[3,2-d]pyrimidine derivatives using pyridine derivatives. 20

    1-2-2 synthesis of pyrido[3,2-d]pyrimidine derivatives under microwave conditions. 21

    1-2-2-1 use of 3,1-dimethylbarbituric acid. 21

    1-2-2-2 use of 6,2-diaminopyrimidin-4-(H3)-one. 21

    1-2-2-3 use of malononitrile. 22

    1-2-2-4 use of 1-phenylmaleimide. 23

    1-2-2-5 use of tetronic acid. 23

    1-2-2-6 use of 2,1-diphenylthanone. 25

    1-2-3 synthesis of pyrido[3,2-d]pyrimidine derivatives under ultrasonic conditions. 26

    1-2-3-1 using 3,1-indandione. 26

    1-2-3-2 use of pyrazolamine. 26

    Chapter Two

    2-1 research objective. 29

    2-2 research method. 30

    2-2-1 Preparation of compound 7-amino-3,1-dimethyl-5-(4-chlorophenyl)-1H-pyrido[3,2-d]pyrimidine-4,2-dione (a93) 30

    2-3 The reaction mechanism. 33

    2-4 Investigating the effective factors of the transaction. 34

    2-4-1 Effect of different catalysts on the reaction. 34

    2-4-2 Effect of K2CO3 catalyst amount on reaction progress. 35

    2-4-3 Investigating the effect of hyperthermia on the progress of the reaction. 36

    2-4-4 Investigating the effect of the solvent on the progress of the reaction. 37

    2-5 Synthesis of pyrido[3,2-d]pyrimidine derivatives using K2CO3 catalyst 37

    2-6 Conclusion. 42

    2-7 suggestions for future work 42

    Chapter 3

    3-1 General techniques. 44

    3-2 General method of pyrido]3,2-[dpyrimidine derivatives. 44

    3-3 preparation. 7-amino-5-(4-chloro.phenyl)-3,1-dimethyl-4,2-dioxo-4,3,2,1-tetrahydropyrido]3,2-[dpyrimidine-6-carbonitrile (a93) 45

    3-4 preparation 7-Amino-5-(2-chloro.phenyl)-3,1-dimethyl-4,2-dioxo-4,3,2,1-tetrahydropyrido]3,2-[dpyrimidine-6-carbonitrile (b93) 46

    3-5 preparation 7-amino-5-(3-nitro.phenyl)-3,1-dimethyl-4,2-dioxo-4,3,2,1-tetrahydropyrido]3,2-[dpyrimidine 47

    -6-carbonitrile (c93) 47

    3-6 preparation 7-Amino-5-(3-bromo-phenyl)-3,1-dimethyl-4,2-dioxo-4,3,2,1-tetrahydropyrido]3,2-[dpyrimidine-6-carbonitrile (d93) 48

    3-7 preparation 7-Amino-5-(4-fluoro.phenyl)-3,1-dimethyl-4,2-dioxo-4,3,2,1-tetrahydropyrido]3,2-pyrimidine-6-carbonitrile ((93e) [d. 49

    3-8 Preparation 7-amino-5-(3-chloro.phenyl)-3,1-dimethyl-4,2-dioxo-4,3,2,1-tetrahydropyrido]3,2-[dpyrimidine-6-carbonitrile (93f) 50

    3-9 preparation 7-amino-5-(4-nitro-phenyl)-3,1-dimethyl-4,2-dioxo-4,3,2,1-tetrahydropyrido]3,2-[dpyrimidine-6-carbonitrile (93g) 51

    3-10Oxo-4,3,2,1-tetrahydropyrido]3,2-[dpyrimidine-6-carbonitrile (93g) 51

    3-10 Preparation of 7-amino-4,2-dioxo-5-phenyl-4,3,2,1-tetrahydropyrido]3,2-[dpyrimidine-6-carbonitrile (a94) 52

    3-11 Preparation of 7-amino-5-(2-chloro.phenyl)-4,2-dioxo-4,3,2,1-tetrahydropyrido]3,2-[dpyrimidine-6-carbonitrile (b94) 53

    3-12 Preparation 7-amino-5-(4-chloro.phenyl)-4,2-dioxo-4,3,2,1-tetrahydropyrido]3,2-[dpyrimidine-6-carbonitrile (c94) 54

    3-13 Preparation of 6-amino-2-thio.oxo-3,2-dihydropyrimidine-4(H1)-one (27) 55

    3-14 preparation of 7-amino-5-(4-fluoro.phenyl)-4-oxo-2-thiooxo-4,3,2,1-tetrahydropyrido]3,2-[dpyrimidine-6-carbonitrile (a95) 56

    3-15 preparation 7-amino-5-(4-chloro.phenyl)-4-oxo-2-thiooxo-4,3,2,1-tetrahydropyrido]3,2-[dpyrimidine-6-carbonitrile (95b) 57

    3-16 preparation 7-amino-4-oxo-5-phenyl-2-thiooxo-4,3,2,1-tetrahydropyrido]3,2-[dpyrimidine-6-carbonitrile (95c) 58

    FT-IR spectrum 7-amino-5-(4-chloro.phenyl)-3,1-dimethyl-4,2-dioxo-4,3,2,1-tetrahydropyrido]3,2-[dpyrimidine-6-carbonitrile (a93) 61

    1H NMR spectrum 7-amino-5-(4-chloro.phenyl)-3,1-dimethyl-4,2-dioxo-4,3,2,1-tetrahydropyrido]3,2-[dpyrimidine-6-carbonitrile (a93) 62

    13C NMR spectrum 7-amino-5-(4-chloro.phenyl)-3,1-dimethyl-4,2-dioxo-4,3,2,1-tetrahydropyrido]3,2-[dpyrimidine-6-carbonitrile (a93) 63

    FT-IR spectrum 7-amino-5-(2-chloro.phenyl)-3,1-dimethyl-4,2-dioxo-4,3,2,1-tetrahydropyrido]3,2-[dpyrimidine-6-carbonitrile (b93) 64

    1H NMR spectrum 7-amino-5-(2-chloro.phenyl)-3,1-dimethyl-4,2-dioxo-4,3,2,1-tetrahydropyrido]3,2-[dpyrimidine-6-carbonitrile (b93) 65

    13C NMR spectrum 7-amino-5-(2-chloro.phenyl)-3,1-dimethyl-4,2-dioxo-4,3,2,1-tetrahydropyrido]3,2-[dpyrimidine-6-carbonitrile (b93) 66

    FT-IR spectrum 7-amino-5-(3-nitro-phenyl)-3,1-dimethyl-4,2-dioxo-4,3,2,1-tetrahydropyrido]3,2-[dpyrimidine-6-carbonitrile (c93) 67

    1H NMR spectrum 7-Amino-5-(3-nitrophenyl)-3,1-dimethyl-4,2-dioxo-4,3,2,1-tetrahydropyrido]3,2-[dpyrimidine-6-carbonitrile (c93) 68

    1H NMR spectrum 7-amino-5-(3-nitro-phenyl)-3,1-dimethyl-4,2-dioxo-4,3,2,1-tetrahydropyrido]3,2-[dpyrimidine-6-carbonitrile (c93) 69

    13C NMR spectrum 7-amino-5-(3-nitro-phenyl)-3,1-dimethyl-4,2-dioxo-4,3,2,1-tetrahydropyrido]3,2-[dpyrimidine-6-carbonitrile (c93) 70

    FT-IR spectrum 7-amino-5-(3-bromo-phenyl)-3,1-dimethyl-4,2-dioxo-4,3,2,1-tetrahydropyrido]3,2-[dpyrimidine-6-carbonitrile (d93) 71

    1H NMR spectrum 7-amino-5-(3-bromo-phenyl)-3,1-dimethyl-4,2-dioxo-4,3,2,1-tetrahydropyrido]3,2-[dpyrimidine-6-carbonitrile (d93) 72

    1H NMR spectrum 7-amino-5-(3-bromo-phenyl)-3,1-dimethyl-4,2-dioxo-4,3,2,1-tetrahydropyrido]3,2-[dpyrimidine-6-carbonitrile (d93) 73

    13C NMR spectrum 7-amino-5-(3-bromo-phenyl)-3,1-dimethyl-4,2-dioxo-4,3,2,1-tetrahydropyrido]3,2-[dpyrimidine-6-carbonitrile (d93) 74

    FT-IR spectrum 7-amino-5-(4-fluoro.phenyl)-3,1-dimethyl-4,2-dioxo-4,3,2,1-tetrahydropyrido]3,2-[dpyrimidine-6-carbonitrile (e93) 75

    1H NMR spectrum 7-amino-5-(4-fluoro.phenyl)-3,1-dimethyl-4,2-dioxo-4,3,2,1-tetrahydropyrido]3,2-[dpyrimidine-6-carbonitrile (e93) 76

    13C NMR spectrum 7-amino-5-(4-fluoro.phenyl)-3,1-dimethyl-4,2-dioxo-4,3,2,1-tetrahydropyrido]3,2-[dpyrimidine-6-carbonitrile (e93) 77

    Spectrum FT-IR7-Amino-5-(3-chloro.phenyl)-3,1-dimethyl-4,2-dioxo-4,3,2,1-tetrahydropyrido]3,2-[dpyrimidine-6-carbonitrile (f93) 78

    1H NMR spectrum 7-amino-5-(3-chloro.phenyl)-3,1-dimethyl-4,2-dioxo-4,3,2,1-tetrahydropyrido]3,2-[dpyrimidine-6-carbonitrile (f93) 79

    13C NMR spectrum 7-amino-5-(3-chloro.phenyl)-3,1-dimethyl-4,2-dioxo-4,3,2,1-tetrahydropyrido]3,2-[dpyrimidine-6-carbonitrile (f93) 80

    FT-IR spectrum 7-amino-5-(4-nitro-phenyl)-3,1-dimethyl-4,2-dioxo-4,3,2,1-tetrahydropyrido]3,2-[dpyrimidine-6-carbonitrile (g93) 81

    1H NMR spectrum 7-Amino-5-(4-nitrophenyl)-3,1-dimethyl-4,2-dioxo-4,3,2,1-tetrahydropyrido]3,2-[dpyrimidine-6-carbonitrile (g93) 82

    13C NMR spectrum 7-amino-5-(4-nitro-phenyl)-3,1-dimethyl-4,2-dioxo-4,3,2,1-tetrahydropyrido]3,2-[dpyrimidine-6-carbonitrile (g93) 83

    FT-IR spectrum 7-amino-4,2-dioxo-5-phenyl-4,3,2,1-tetrahydropyrido]3,2-[dpyrimidine-6-carbonitrile. (a94) 84

    1H NMR spectrum of 7-amino-4,2-di.

An efficient method for the synthesis of pyrido[3,2-d]pyrimidine derivatives
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