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  3. Effective three-component synthesis of new 4-aryl-5-(tert-butyl-amino)-2-(1-methyl-1H-pyrrol-2-yl)furan-3-carbonitrile derivatives

Effective three-component synthesis of new 4-aryl-5-(tert-butyl-amino)-2-(1-methyl-1H-pyrrol-2-yl)furan-3-carbonitrile derivatives

Number of pages: 71 File Format: word File Code: 31865
Year: 2014 University Degree: Master's degree Category: Chemical - Petrochemical Engineering
Tags/Keywords: carbonitrile - Effective three-component synthesis - eruption - Multicomponent reactions - Oxopropane nitrile - Pyrrol - synthesis - Tertiary-butylamino
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  • Summary of Effective three-component synthesis of new 4-aryl-5-(tert-butyl-amino)-2-(1-methyl-1H-pyrrol-2-yl)furan-3-carbonitrile derivatives

    Academic thesis for obtaining a master's degree

    Chemistry, organic orientation

    Abstract:

    Title: Effective three-component synthesis of new derivatives 4-aryl-5-(tert-butylamino)-2-(1-methyl-1H-pyrrol-2-yl)furan-3-carbonitrile Three components 3-(1-methyl-1H-pyrrol-2-yl)-3-oxopropanenitrile, tert-butyl isocyanide and aromatic aldehydes, in EtOH solvent and using DABCO as a catalyst under reflux conditions are presented. In this method, new derivatives of 4-aryl-5-(tert-butylamino)-2-(1-methyl-1H-pyrrol-2-yl)-furan-3-carbonitrile were synthesized with yields of 65-80%. Ar = 4-MeC6H4, 4-MeOC6H4, 4-ClC6H4, 4-MeSC6H4, 4-BrC6H4, 2,4-Cl2C6H3, 4-O2NC6H4

    Key words: 4-aryl-5-aminofuran, multicomponent reactions, 3-(1-methyl-1H-pyrrol-2-yl)-3-oxo Propane nitrile

    1- Introduction

    Considering that in this thesis 4-aryl-5-aminofurans with pyrrole substitution have been studied using multicomponent reactions, first a short introduction about multicomponent, pyrrole and furan reactions is provided.

    Multicomponent Reactions

    Multicomponent reactions have been known for over 150 years. In these reactions, three or more reactants participate together in a chemical reaction to form a product that contains significant parts of all the primary components of the reaction.

    Multicomponent reactions have attracted a lot of attention in synthetic chemistry in industry and academia due to the ease of implementation, time saving, and generally high efficiency and reduction in the formation of unwanted products. These reactions are very beneficial from an economic point of view, and their application in the discovery of drugs, materials science and the synthesis of natural substances shows their high importance [1-3].

    Pyrrole

    The chemistry of heterocyclic compounds is one of the attractive branches of organic chemistry and includes the most diverse synthetic methods. The synthesis of these compounds was mainly developed from 1950 onwards. Pyrrole is a basic heterocyclic compound, colorless, volatile, insoluble in water and soluble in alcohol and ether. Pyrrole and its derivatives are widely used as intermediates in the synthesis of pharmaceuticals, chemical and agricultural materials, dyes, photographic chemicals, fragrances, and other organic compounds. They are also used as catalysts in polymerization processes, food inhibitors and preservatives. Other uses of pyrrole derivatives include wide biological and medicinal activities such as antibacterial, anti-inflammatory, anti-fungal and anti-tumor. Figure 1-1 shows the structure of two pyrrole derivatives (1,2) with medicinal properties [4]. Antitumor

    2 1

    Figure 1-1 pyrrole derivatives with medicinal properties.

    Furan

    Heterocyclic furan containing a five-membered aromatic ring with four carbon atoms and one atom is oxygen This substance is colorless, flammable, with high volatility and boiling point close to room temperature. Furan is soluble in most organic solvents such as alcohol, ether and acetone, but it is not soluble in water. Substitutive furans are very important in medicinal chemistry and synthesis, so aryl furans have attracted much attention.Furan and many of its derivatives exist in nature and are also found in the structure of sugars with hydroxyl substitutions. Most of the eruptions have significant medicinal properties such as anti-cancer, anti-tumor, anti-inflammatory, anti-bacterial and anti-fungal. In Figure 2-1, the structure of a number of furan derivatives (5-3) with medicinal properties is presented.

    images are available in the main file)

    1-3-1 Overview of the various synthetic methods of furan containing derivatives

    Furan synthesis methods It is widespread and here some of these methods are explained for the preparation of explosive eruptions.

    1-3-1-1 Use of 4-methylene-2-nitro-5-oxo-3-phenyl-heptanoic acid ethyl ester

    In a report, acrylic acid ethyl ester (6) in the presence of hydrogen Bromide gives compound 7, which is further converted to 8 with ethyl nitroacetate and Dabco catalyst (Scheme 1-1). Then the keto ester 8 reacts with aromatics in sulfuric acid containing a few drops of trifluoroacetic acid to obtain 3-benzyl-5-ethyl-2-methyl-4-phenyl-furan (9) with a yield of 43-49% (

    Abstract:

    An Efficient three-component synthesis of novel derivatives of 4-aryl-5-(tert-butylamino)-2-(1-methyl-1H-pyrrol-2-yl)furan-3-carbonitrile.

    In this research a direct and efficient method for the preparation of novel 4-aryl-5-aminofuran derivatives, was devised by employing one-pot three-component reaction of 3-(1-methyl-1H-pyrrol-2-yl)-3-oxopropanenitrile, tert-butyl isocyanide and arylaldehydes in EtOH and using DABCO as catalyst under reflux conditions 4-aryl-5-(tert-butyl-amino)-2-(1-methyl-1H-pyrrol-2-yl)-furan-3-carbonitrile derivatives were synthesized in 65-80% yields.

  • Contents & References of Effective three-component synthesis of new 4-aryl-5-(tert-butyl-amino)-2-(1-methyl-1H-pyrrol-2-yl)furan-3-carbonitrile derivatives

    List:

    Persian abstract..1

    English abstract..b

    Chapter one: introduction and conclusion.2

    1- Introduction..3

    1-1 multicomponent reactions.3

    1-2 pyrrole..3

    1-3 furan..4

    1-3-1 overview of various methods Synthesis of substituted furans. 6

    1-3-1-1 using 4-methylene-2-nitro-5-oxo-3-phenyl-heptanoic acid ethyl ester. 6

    1-3-1-2 preparation from cyanoacetylindole. 7

    1-3-1-3 using aroyl chloride and dialkyl acetylene di carboxylate. 9

    1-3-1-4 using compounds of 3,1-dicarbonyl and propargyl alcohols. 10

    1-3-1-5 using alkyne-4,1-diols in the presence of ruthenium catalyst. 11

    1-3-1-6 using arylidene malonates and 4,1-butene diols. 12

    1-3-1-7 preparation from ketones and halo ketones. 13

    1-3-1-8 using oxidation of 4,1-dihydropyridines. 14

    1-3-1-9 preparation from 3-acetyl-1-aryl-2-pentene-4,1-diones. 14

    1-3-1-10 preparation from ester and alkyne bromide In the presence of a Lewis acid and a base. 15

    Title

    1-3-1-11 Preparation of azulene-3-oxopropionitrile. 15

    Chapter two: discussion and conclusion. 17

    2-1 research objective.. 18

    2-2 Preparation of 3-(1-Methyl-1H-2-yl)-3-oxopropanenitrile.19

    2-3 Preparation of 5-(tert-butylamino)-2-(1-methyl-1H-pyrrol-2-yl)-4-(p-tolyl)-furan-3-carbonitrile (a49)..20

    Mechanism..27

    Result Giri..31

    Suggestion for future works.31

    Chapter three: experimental works.32

    3- Experimental works..33

    3-1 preparation of 5-(tert-butylamino)-2-(1-methyl-1H-pyrrol-2-yl)-4-para-tolyl-furan-3-carbonitrile (a49) ..34

    3-2 Preparation of 5-(tert-butylamino)-4-(4-methoxyphenyl)-2-(1-methyl-1H-pyrrol-2-yl)-furan-3-carbonitrile (b49)..36

    3-3 Preparation of 5-(tert-butylamino)-4-(4-chloro) Phenyl)-2-(1-methyl-1H-pyrrol-2-yl)-furan-3-carbonitrile (c49).

    3-5 Preparation of 4-(4-bromophenyl)-5-(tert-butylamino)-2-(1-methyl-1H-pyrrol-2-yl)-furan-3-carbonitrile (e49)..39

    Title

    3-6 Preparation of 5-(tert-butyl) Amino)-4-(4,2-dichlorophenyl)-2-(1-methyl-1H-pyrrol-2-yl)-furan-3-carbonitrile (f49). (g49). Tolyl-furan-3-carbonitrile (a49) FT-IR 44 1H NMR 45 13C NMR 5-(tert-butylamino)-4-(4-methoxyphenyl)-2-(1-methyl-1H-pyrrol-2-yl)-furan-3-carbonitrile (b49) FT-IR. FT-IR ..50

    1H NMR ..51

    13C NMR ..52

    Title 5-(tert-butylamino)-2-(1-methyl-1H-pyrrol-2-yl)-4-(4-methyl) sulfonyl-phenyl)-furan-3-carbonitrile (d49)

    FT-IR ..53

    1H NMR ..54

    13C NMR ..55

    4-(4-bromophenyl)-5-(tert-butyl) Amino)-2-(1-methyl-1H-pyrrol-2-yl)-furan-3-carbonitrile (e49)

    FT-IR ..56

    1H NMR ..57

    13C NMR ..58

    5-(tert-butylamino)-4-(4,2-dichloro) Phenyl)-2-(1-methyl-1H-pyrrol-2-yl)-furan-3-carbonitrile (f49)

    FT-IR ..59

    1H NMR ..60

    13C NMR ..61

    5-(tert-butylamino)- 2-(1-Methyl-1H-pyrrol-2-yl)-4-(4-nitrophenyl)-furan-3-carbonitrile (g49) FT-IR ..62 1H NMR ..63 13C NMR ..64 Source: 1] Quiroga, J.; Cruz; Cruz, S.; Insuasty, B.; Abonia, M.; Cobo, J. Tetrahedron Lett. 2006, 47, 27-30. [2] Mont, N.; Teixido, J.; Borrell, I. J.; Kappe, C. O. Tetrahedron Lett. 2003, 44, 5385-5389. [3] Dabiri, M.; A-Nezhad, H.; Khavasi, H. R.; Bazgir, A. Tetrahedron 2007, 63, 1770-1774.

    [4] Bouachrin, O.; Hammouti, M.; Elidrissi, B.; Hamidi, A. Portu. Electrochimi. 2008, 26, 283-285. [5] Zanatta, N.; Alves, S. H.; Coelho, H. S.; Borchhardt, D. M.; Machado, P.; Flores, K. M.; da Silva, F. M.; Spader, T. B.; Santurio, J.M.; Martins, A.P. Bioorgan. Med. Chem. 2007, 15, 1947–1958. 

    [6] Dong, Y.; Nakagawa-Goto, K.; Lai, Ch.; Kim, Y.; Morris, S. L.; Lee, P.; Bastow, K. F.;      Lee, K. Bioorg. Med. Chem. Lett. 2011, 21, 52-57.                                                                               

    [7] Wang, F.; Sun, J.; Huang, M.; Wang, H; Sun, P.; Lin, J.; Chen, W. Eur. J. Med. Chem. 2014, 72, 35-45.          

    [8] Shchekotikhin, A. E.; Glazunova, V. A.; Dezhenkova, L. G.; Shevtsova, E. K.; Traven, V.F.; Balzarini, J.; Huang, H.; Shtil, A. A.; Preobrazhenskaya, M. N. Eur. J. Med. Chem. 2011, 46, 42, 423-428.                                                                                                                                  

    [9] Lee, K. Y.; Gowrisankar, S.; Ju Leeb, Y.; Nyoung Kim, J. Tetrahedron 2006, 62, 8798–8804.

    [10] Sun, C.; Ji, S.; Liu, Y.; Tetrahedron Lett. 2007, 48, 8987–8989.

    [11] Yavari, I.; Mokhtarporyani, A.; Moradi, L.; Mirzaei, A. Tetrahedron 2008, 64, 5221–5225. [12] Chatterjee, P. N.; Roy, S. Tetrahedron 2011, 67, 4569–4577.

    [13] Pridmore, S. J.; Slatford, P. A.; Taylor, J.E.; Whittlesey, M. K.; Williams, J. M. J. Tetrahedron 2009, 65, 8981–8986

    [14] Wang, T.; Zhiliang, J, L.; Zhong, H.; Chen, H.; Niu, Ch.; Li, K. Tetrahedron 2011, 67, 3476–3482.

    [15] York, M. Tetrahedron Lett. 2011, 52, 6267-6270.

    [16] Liu, Zh.; Yu, W.; Yang, L.; Liu, Zh. L. Tetrahedron Lett. 2007, 48, 5321-5324. [17] Onitsuka, S.; Nishino, H. Tetrahedron 2003, 59, 755–765.

    [18] Zeng, W.; Wu, W.; Jiang, H.; Sun, Y.; Chen, Zh. Tetrahedron Lett. 2013, 54, 4605.4609.

    [19] Wanga, D. L.; Dong, Zh.; Xu, J.; Li, D. Chin. Chem. Lett. 2013, 24, 622–624.

Effective three-component synthesis of new 4-aryl-5-(tert-butyl-amino)-2-(1-methyl-1H-pyrrol-2-yl)furan-3-carbonitrile derivatives
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