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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 36, 2006 - Issue 2
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Original Articles

Synthesis of N‐Substituted 4,6‐Dimethyl‐3‐cyano‐2‐pyridones Under Microwave Irradiation

Dušan Mijin Department of Organic Chemistry, Faculty of Technology and Metallurgy, University of Belgrade, Belgrade, Serbia and MontenegroCorrespondence[email protected]
&
Aleksandar Marinković Department of Organic Chemistry, Faculty of Technology and Metallurgy, University of Belgrade, Belgrade, Serbia and Montenegro
Pages 193-198 | Received 23 May 2005, Published online: 15 Aug 2006

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Y. Shyma Mary, Yohannan Sheena Mary, Renjith Thomas & B. Narayana. (2022) Detailed Study of Three Halogenated Benzylpyrazole Acetamide Compounds with Potential Anticancer Properties. Polycyclic Aromatic Compounds 42:9, pages 6705-6719.
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Masoud Mohamadi Vala, Mohammad Bayat & Yadollah Bayat. (2020) Synthesis of highly functionalized hydropyridones: thiazolo[3,2-a]pyridin-5-one-6-carbohydrazones and tetrahydroimidazo[1,2-a]pyridin-5-one-2-carbohydrazones. Journal of Sulfur Chemistry 41:5, pages 542-560.
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Navjeet Kaur. (2015) Six-Membered N-Heterocycles: Microwave-Assisted Synthesis. Synthetic Communications 45:1, pages 1-34.
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Prakash S. Nayak, Badiadka Narayana, Sumati Anthal, Vivek K. Gupta & Rajni Kant. (2014) Synthesis, Crystal Structure, and Characterization of 2-Phenyl-N-(pyrazin-2-yl)Acetamide. Molecular Crystals and Liquid Crystals 592:1, pages 199-208.
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JasminaM. Dostanić, DavorR. Lončarević, PredragT. Banković, OlgaG. Cvetković, DušanM. Jovanović & Dušan Ž. Mijin. (2011) Influence of process parameters on the photodegradation of synthesized azo pyridone dye in TiO2 water suspension under simulated sunlight. Journal of Environmental Science and Health, Part A 46:1, pages 70-79.
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Articles from other publishers (43)

Tanja Lunić, Jelena Lađarević, Marija Mandić, Vanja Veruševski, Biljana Božić Nedeljković, Dušan Mijin & Bojan Božić. (2022) Antioxidant and neuroprotective activities of selected 2-pyridones: In vitro and in silico study. Journal of Molecular Structure 1256, pages 132546.
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Manuel Faúndez-Parraguez, Carlos Alarcón-Miranda, Young Hwa Cho, Hernán Pessoa-Mahana, Carlos Gallardo-Garrido, Hery Chung, Mario Faúndez & David Pessoa-Mahana. (2021) New Pyridone-Based Derivatives as Cannabinoid Receptor Type 2 Agonists. International Journal of Molecular Sciences 22:20, pages 11212.
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Zainab Almarhoon, Hessa H. Al Rasheed & Ayman El-Faham. (2020) Ultrasonically Assisted N -Cyanoacylation and Synthesis of Alkyl(4-(3-cyano-4,6-dimethyl-2-oxopyridin-1(2 H )-yl)benzoyl)amino Acid Ester Derivatives . ACS Omega 5:47, pages 30671-30678.
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Hajar Hosseini & Mohammad Bayat. (2018) An efficient and ecofriendly synthesis of highly functionalized pyridones via a one-pot three-component reaction . RSC Advances 8:48, pages 27131-27143.
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R. Shahidha, S. Muthu, M. Raja, R. Raj Muhamed, B. Narayana, Prakash S. Nayak & B.K. Sarojini. (2017) Spectroscopic (FT-IR, FT-Raman), first order hyperpolarizabilities, NBO, Fukui function and molecular docking study of N-(4-Chloro-3-methylphenyl)-2-phenylacetamide. Optik 140, pages 1127-1142.
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Badiadka Narayana, Hemmige S. Yathirajan, Ravindranath Rathore & Christopher Glidewell. (2016) Crystal structures of two C,N-disubstituted acetamides: 2-(4-chlorophenyl)- N -(2-iodophenyl)acetamide and 2-(4-chlorophenyl)- N -(pyrazin-2-yl)acetamide . Acta Crystallographica Section E Crystallographic Communications 72:9, pages 1270-1275.
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Ahmed A. Fadda & Ramy Rabie. (2015) Cyanoacetylation of amines: recent advances in preparation methods and their synthetic uses in the formation of biologically active compounds. Research on Chemical Intermediates 42:2, pages 771-811.
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Moustafa Ahmed Gouda, Meshal Abdulrahim Sabah, Waled Khaled Aljuhani, Ahmed Saleh El-Gahani, Snad Abd El-Karem El-Enazi, Salem Atalleh Al Enizi & Majed Musallam Al-Balawi. (2015) Utility of 2-cyano-N-(2-hydroxyethyl) acetamide in heterocyclic synthesis. European Journal of Chemistry 6:2, pages 219-224.
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M. Ben Messaouda, A. Mahjoub, M. Mogren Al-Mogren, M. Abderrabba & M. Hochlaf. (2014) Substituent effects on vibrational and electronic excitation spectra of pyridone tautomers and ions: The case of the cyano group. Journal of Molecular Structure 1074, pages 422-428.
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Manpreet Kaur, Jerry P. Jasinski, H. S. Yathirajan, B. Narayana & K. Byrappa. (2014) N -(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1 H -pyrazol-4-yl)-2-(4-nitrophenyl)acetamide . Acta Crystallographica Section E Structure Reports Online 70:6, pages o636-o637.
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V. Arjunan, S. Senthilkumari, P. Ravindran & S. Mohan. (2014) Synthesis, FTIR and FT-Raman spectral analysis and structure–activity relations of N-(4-bromophenyl)-2,2-dichloroacetamide by DFT studies. Journal of Molecular Structure 1064, pages 15-26.
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A. S. Praveen, H. S. Yathirajan, Jerry P. Jasinski, Amanda C. Keeley, B. Narayana & B. K. Sarojini. (2013) 2-(4-Chlorophenyl)- N -(3,4-difluorophenyl)acetamide . Acta Crystallographica Section E Structure Reports Online 69:6, pages o996-o997.
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A.S. Praveen, H. S. Yathirajan, Jerry P. Jasinski, Amanda C. Keeley, B. Narayana & B. K. Sarojini. (2013) 2-(4-Bromophenyl)- N -(3,4-difluorophenyl)acetamide . Acta Crystallographica Section E Structure Reports Online 69:6, pages o900-o901.
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Prakash S. Nayak, B. Narayana, Jerry P. Jasinski, H. S. Yathirajan & B. K. Sarojini. (2013) 2-(4-Bromophenyl)- N -(pyrazin-2-yl)acetamide . Acta Crystallographica Section E Structure Reports Online 69:6, pages o891-o891.
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Prakash S. Nayak, B. Narayana, H. S. Yathirajan, Jerry P. Jasinski & Ray J. Butcher. (2013) 2-(2,4-Dichlorophenyl)- N -(1,3-thiazol-2-yl)acetamide . Acta Crystallographica Section E Structure Reports Online 69:5, pages o656-o657.
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Prakash S. Nayak, B. Narayana, H. S. Yathirajan, Jerry P. Jasinski & Ray J. Butcher. (2013) 2-(3,4-Dichlorophenyl)- N -(1,3-thiazol-2-yl)acetamide . Acta Crystallographica Section E Structure Reports Online 69:5, pages o645-o646.
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Ismail Ajaj, Du?an Mijin, Veselin Maslak, Danijela Brkovi?Milo? Mil?i?Nina Todorovi?Aleksandar Marinkovi?. (2013) A simple and convenient synthesis of tautomeric (6 or 2)-hydroxy-4-methyl-(2 or 6)-oxo-1-(substituted phenyl)-(1,2 or 1,6)-dihydropyridine-3-carbonitriles. Monatshefte f?r Chemie - Chemical Monthly 144:5, pages 665-675.
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Prakash S. Nayak, B. Narayana, H. S. Yathirajan, Jerry P. Jasinski & Ray J. Butcher. (2013) 2-(2,6-Dichlorophenyl)- N -(1,3-thiazol-2-yl)acetamide . Acta Crystallographica Section E Structure Reports Online 69:4, pages o523-o523.
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Ray J. Butcher, Aneeka Mahan, P. S. Nayak, B. Narayana & H. S. Yathirajan. (2012) 2-(2,6-Dichlorophenyl)- N -(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1 H -pyrazol-4-yl)acetamide . Acta Crystallographica Section E Structure Reports Online 69:1, pages o46-o47.
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Ray J. Butcher, Aneeka Mahan, P. S. Nayak, B. Narayana & H. S. Yathirajan. (2012) 2-(2,4-Dichlorophenyl)- N -(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1 H -pyrazol-4-yl)acetamide . Acta Crystallographica Section E Structure Reports Online 69:1, pages o39-o39.
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Adel S. A. Alimmari, Bojan Đ. Božić, Aleksandar D. Marinković, Dušan Ž. Mijin & Gordana S. Ušćumlić. (2012) Solvent and Structural Effects on the UV–Vis Absorption Spectra of Some 4,6-Disubstituted-3-Cyano-2-Pyridones. Journal of Solution Chemistry 41:10, pages 1825-1835.
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Hoong-Kun Fun, Chin Wei Ooi, Prakash S. Nayak, B. Narayana & B. K. Sarojini. (2012) N -(3,4-Difluorophenyl)-2,2-diphenylacetamide . Acta Crystallographica Section E Structure Reports Online 68:5, pages o1349-o1350.
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Hoong-Kun Fun, Tze Shyang Chia, Prakash S. Nayak, B. Narayana & B. K. Sarojini. (2012) N -(2,4-Dimethylphenyl)-2,2-diphenylacetamide . Acta Crystallographica Section E Structure Reports Online 68:5, pages o1316-o1317.
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Hoong-Kun Fun, Chin Wei Ooi, Prakash S. Nayak, B. Narayana & B. K. Sarojini. (2012) 2,2-Diphenyl- N -(1,3-thiazol-2-yl)acetamide . Acta Crystallographica Section E Structure Reports Online 68:5, pages o1312-o1313.
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Hoong-Kun Fun, Tze Shyang Chia, Prakash S. Nayak, B. Narayana & B. K. Sarojini. (2012) N -(2,6-Dimethylphenyl)-2,2-diphenylacetamide . Acta Crystallographica Section E Structure Reports Online 68:5, pages o1287-o1288.
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Hoong-Kun Fun, Tara Shahani, Prakash S. Nayak, B. Narayana & B. K. Sarojini. (2012) N -(4-Bromophenyl)-2-(4-chlorophenyl)acetamide . Acta Crystallographica Section E Structure Reports Online 68:2, pages o519-o519.
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A. S. Praveen, Jerry P. Jasinski, James A. Golen, H. S. Yathirajan & B. Narayana. (2011) N -(4,6-Dimethoxypyrimidin-2-yl)-2-(3-methylphenyl)acetamide . Acta Crystallographica Section E Structure Reports Online 68:1, pages o226-o227.
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Hoong-Kun Fun, Ching Kheng Quah, B. Narayana, Prakash S. Nayak & B. K. Sarojini. (2011) N -(3,5-Dichlorophenyl)-2-(naphthalen-1-yl)acetamide . Acta Crystallographica Section E Structure Reports Online 67:11, pages o2941-o2942.
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Hoong-Kun Fun, Ching Kheng Quah, B. Narayana, Prakash S. Nayak & B. K. Sarojini. (2011) N -(4-Bromophenyl)-2-(naphthalen-1-yl)acetamide . Acta Crystallographica Section E Structure Reports Online 67:11, pages o2926-o2927.
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Richard Betz, Thomas Gerber, Eric Hosten, Maravanahalli S. Siddegowda & Hemmige S. Yathirajan. (2011) 3-Chloro- N -(4-methoxyphenyl)propanamide . Acta Crystallographica Section E Structure Reports Online 67:11, pages o2868-o2868.
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Sunil S. Chavan & Mariam S. Degani. (2011) Ionic Liquid Catalyzed 4,6-Disubstituted-3-Cyano-2-Pyridone Synthesis Under Solvent-Free Conditions. Catalysis Letters 141:11, pages 1693-1697.
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A. S. Praveen, Jerry P. Jasinski, James A. Golen, B. Narayana & H. S. Yathirajan. (2011) N -(3-Chloro-4-fluorophenyl)-2,2-diphenylacetamide . Acta Crystallographica Section E Structure Reports Online 67:10, pages o2604-o2604.
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A. S. Praveen, Jerry P. Jasinski, James A. Golen, H. S. Yathirajan & B. Narayana. (2011) N -(4-Chloro-1,3-benzothiazol-2-yl)-2-(3-methylphenyl)acetamide monohydrate . Acta Crystallographica Section E Structure Reports Online 67:10, pages o2602-o2603.
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Abdel-Zaher A. Elassar. (2011) Synthesis and reactions of 3-cyano-4,6-dimethyl-2-pyridone. Journal of Heterocyclic Chemistry 48:2, pages 272-278.
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Majid M. Heravi, Leili Tahershamsi, Hossein A. Oskooie & Bita Baghernejad. (2010) 1,4‐Diaza‐bicyclo[2,2,2]octane as a Novel and Efficient Catalyst for the Synthesis of 3,4,6‐Trisubstituted 2‐Pyridone Derivatives. Chinese Journal of Chemistry 28:4, pages 670-672.
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Zhu-Ping Xiao, Yu-Zhu Ouyang, Shi-Dong Qin, Tian Xie & Jia Yang. (2009) 2-(4-Bromophenyl)- N -(2-methoxyphenyl)acetamide . Acta Crystallographica Section E Structure Reports Online 66:1, pages o67-o67.
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Aleksandar D. Marinković, Bratislav Ž. Jovanović, Nina Todorović & Ivan O. Juranić. (2009) Linear free energy relationships of the 1H and 13C NMR chemical shifts in 3-cyano-4-(substituted phenyl)-6-phenyl-2(1H)pyridones. Journal of Molecular Structure 920:1-3, pages 90-96.
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Aleksandar MarinkovicD.D., Tatjana VasiljevicM.M., Mila LausevicD.D. & Bratislav JovanovicZ.Z.. (2009) ESI-MS spectra of 3-cyano-4-(substituted phenyl)-6-phenyl-2(1H)-pyridinones. Journal of the Serbian Chemical Society 74:3, pages 223-235.
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V. D. Dyachenko, R. P. Tkachiov & O. S. Bityukova. (2008) Chemical properties of cyanoacetanilides and synthesis of biologically active compounds around them. Russian Journal of Organic Chemistry 44:11, pages 1565-1579.
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Dusan MijinZ.Z., Masa Prascevic & Slobodan PetrovicD.D.. (2008) Benzylation of N-phenyl-2-phenylacetamide under microwave irradiation. Journal of the Serbian Chemical Society 73:10, pages 945-950.
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Aleksandar MarinkovicD.D., Natasa ValenticV.V., Dusan MijinZ.Z., Gordana UscumlicG.G. & Bratislav JovanovicZ.Z.. (2008) 13C- and 1H-NMR substituent-induced chemical shifts in N(1)-(4-substituted phenyl)-3-cyano-4,6-dimethyl-2-pyridones. Journal of the Serbian Chemical Society 73:5, pages 513-524.
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Dusan Mijin & Aleksandar Marinkovic. (2006) Synthesis of N‐Substituted 4,6‐Dimethyl‐3‐cyano‐2‐pyridones under Microwave Irradiation.. ChemInform 37:23.
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Dusan MijinZ.Z. & Slobodan PetrovicD.D.. (2005) Microwaves in organic chemistry and organic chemical. Hemijska industrija Chemical Industry 59:9-10, pages 224-229.
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