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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 8
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Original Articles

Facile Synthesis of 2‐Amino‐1,4‐naphthoquinones catalyzed by Molecular Iodine under Ultrasonic Irradiation

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Pages 1201-1211 | Received 10 May 2007, Published online: 17 Apr 2008

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Najmeh Mehrmand, Mostafa Keshavarz Moraveji & Arsalan Parvareh. (2022) Adsorption of Pb(II), Cu(II) and Ni(II) ions from aqueous solutions by functionalised henna powder (Lawsonia Inermis); isotherm, kinetic and thermodynamic studies. International Journal of Environmental Analytical Chemistry 102:1, pages 1-22.
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Laila Baddi, Driss Ouzebla, Az-Eddine El Mansouri, Michael Smietana, Jean-Jacques Vasseur & Hassan B. Lazrek. (2021) Efficient one-pot, three-component procedure to prepare new α-aminophosphonate and phosphonic acid acyclic nucleosides. Nucleosides, Nucleotides & Nucleic Acids 40:1, pages 43-67.
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Hong-She Wang & Jun-E Zeng. (2010) Iodine-Catalyzed, Efficient Synthesis of α-Hydroxy Phosphonates in Water. Phosphorus, Sulfur, and Silicon and the Related Elements 185:7, pages 1425-1428.
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Rui-Zhi Wang, Li-Feng Zhang & Zhen-Shui Cui. (2009) Iodine-Catalyzed Synthesis of 12-Aryl-8,9,10,12-tetrahydro-benzo[a]xanthen-11-one Derivatives via Multicomponent Reaction. Synthetic Communications 39:12, pages 2101-2107.
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Abdolali Alizadeh, Hamidreza Hasanpour & Reza Rezaiyehraad. (2023) Efficient, Concise, and Chemoselective Synthesis of 1 H ‐Benzo[ f ]indole‐4,9‐dione with 4‐Hydroxycoumarin Substituent via a One‐Pot Three‐Component Reaction . ChemistrySelect 8:48.
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Yu Dong, Yong Chen, Zhan-Yuan Zhang, Jun-Hu Qian, Zhen-Zhen Peng, Bo Chang, Zhi-Chuan Shi, Zhong-Hui Li & Bing He. (2023) A one-pot access to 2-(N-substituted Amino)-Quinones or 3-indolyl-Quinones from naphthol/hydroquinone. Tetrahedron 135, pages 133337.
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Aesha F. S. H. Abdassalam, Nahide Gulsah Deniz, Cigdem Sayil, Evren Onay-Ucar, Elif Mertoglu & Nazli Arda. (2023) Novel vitamin K3 analogs containing 3-N-substituted aromatic and piperazine rings with selective in vitro anticancer activity against HeLa, U87 MG, and MCF-7 cells. Medicinal Chemistry Research 32:3, pages 475-484.
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Pintu Karmakar, Indrajit Karmakar, Debopam Pal, Suravi Das & Goutam Brahmachari. (2023) Electrochemical Regioselective C( sp 2 )–H Selenylation and Sulfenylation of Substituted 2-Amino-1,4-naphthoquinones . The Journal of Organic Chemistry 88:2, pages 1049-1060.
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Nayana Nayek & Goutam Brahmachari. (2022) Visible‐Light‐Mediated Self‐Sensitized Oxidative and Regioselective C(sp 2 )−H Selenylation and Sulfenylation of Substituted 2‐Amino‐1,4‐Naphthoquinones . European Journal of Organic Chemistry 26:2.
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Mayurakhi Bhuyan & Gakul Baishya. (2022) BiCl 3 catalyzed synthesis of 2-amino-1,4-naphthoquinones and 1,4-naphthoquinon-2-sulfides and one-pot sequential amine-arylation of 1,4-naphthoquinone . Organic & Biomolecular Chemistry 20:46, pages 9172-9183.
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Bhawana Nagar & Basab Bijayi Dhar. (2022) Visible Light-Mediated Thiolation of Substituted 1,4-Naphthoquinones Using Eosin Y as a Photoredox Catalyst. The Journal of Organic Chemistry 87:5, pages 3195-3201.
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Angélica Lauria Nascimento Mello, Fernanda Savacini Sagrillo, Alan Gonçalves de Souza, Amanda Rodrigues Pinto Costa, Vinícius Rangel Campos, Anna Claudia Cunha, Ricardo Imbroisi Filho, Fernanda da Costa Santos Boechat, Mauro Sola-Penna, Maria Cecília Bastos Vieira de Souza & Patricia Zancan. (2021) Selective AMPK activator leads to unfolded protein response downregulation and induces breast cancer cell death and autophagy. Life Sciences 276, pages 119470.
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O. P. Shestak, V. L. Novikov & V. P. Glazunov. (2021) Direct amination of naphthopurpurin and mompain, sea urchin pigments, and their O-methyl ethers by the reaction with ammonia. Russian Chemical Bulletin 70:4, pages 792-804.
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Yu Dong, Ting Mei, Qi-Qi Luo, Qiang Feng, Bo Chang, Fan Yang, Hong-wei Zhou, Zhi-Chuan Shi, Ji-Yu Wang & Bing He. (2021) t -BuOK mediated oxidative coupling amination of 1,4-naphthoquinone and related 3-indolylnaphthoquinones with amines . RSC Advances 11:12, pages 6776-6780.
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David Ríos, Jaime A. Valderrama, Miriam Cautin, Milko Tapia, Felipe Salas, Angélica Guerrero-Castilla, Giulio G. Muccioli, Pedro Buc Calderón & Julio Benites. (2020) New 2-Acetyl-3-aminophenyl-1,4-naphthoquinones: Synthesis and In Vitro Antiproliferative Activities on Breast and Prostate Human Cancer Cells . Oxidative Medicine and Cellular Longevity 2020, pages 1-11.
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Fazhou Yang, Ziyan Liu, Hao Liu, Yu Shangguan, Hao Deng, Jiaxing Huang, Yumei Xiao, Hongchao Guo & Cheng Zhang. (2020) Cu-Catalysed synthesis of benzo[ f ]indole-2,4,9(3 H )-triones by the reaction of 2-amino-1,4-napthoquinones with α-bromocarboxylates . Organic & Biomolecular Chemistry 18:34, pages 6724-6731.
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Andivelu Ilangovan & Thumadath Palayullaparambil Adarsh Krishna. 2020. Organic Synthesis - A Nascent Relook [Working Title]. Organic Synthesis - A Nascent Relook [Working Title].
N. Nurhikmah, A. H. Cahyana & A. R. Liandi. Utilization of cinnamaldehyde for synthesis of nitrogen-containing 2-hydroxy-1,4-naphthoquinone derivatives as antioxidant agent. Utilization of cinnamaldehyde for synthesis of nitrogen-containing 2-hydroxy-1,4-naphthoquinone derivatives as antioxidant agent.
Hassan Vasheghani Farahani, Mohammad Bayat & Shima Nasri. (2019) Synthesis of New 2-Amino-3-(2-Oxothiazol-Methyl)-Substituted-1,4-Naphthoquinone Derivatives Based on Silica Nanoparticles as a Reusable Heterogeneous Catalyst. Silicon 12:1, pages 41-48.
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Yu Shangguan, Fazhou Yang, Hao Deng, Hao Liu, Ziyan Liu, Wanyue Zhuang, Chenxi Qiao, Aizheng Wang, Yumei Xiao & Cheng Zhang. (2019) Copper-Catalyzed Three-Component Difunctionalization of Aromatic Alkenes with 2-Amino-1,4-naphthoquinones and α-Bromocarboxylates. The Journal of Organic Chemistry 84:17, pages 10649-10657.
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L. M. Gornostaev, E. V. Nuretdinova, T. I. Lavrikova, Yu. G. Khalyavina, O. I. Fominykh & Yu. V. Gatilov. (2019) On the Reaction of 2-Benzylamino-1,4-naphthoquinones with Nitrosylsulfuric Acid. Russian Journal of Organic Chemistry 55:5, pages 608-614.
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Kıymet Berkil Akar, Eda Mercan, Barış Eran & Bilge Hilal Çadırcı. (2018) Synthesis and Biological Evaluation of Novel 5,8-Dibromo-2-N-substituted-1,4-Naphthoquinone Derivatives as Potential Antimicrobial Agents. Cumhuriyet Science Journal 39:3, pages 608-614.
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Polu Ashok & Andivelu Ilangovan. (2018) Transition metal mediated selective C vs N arylation of 2-aminonaphthoquinone and its application toward the synthesis of benzocarbazoledione. Tetrahedron Letters 59:5, pages 438-441.
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Sujeong Shin, Haneul Lee, Cheolmin Jeon, Umma Hafsa Preya, Jung‐Hye Choi & Jeong Ho Park. (2017) Anticancer Activity of 2‐Amino‐substituted‐1,4‐naphthoquinone Derivatives in Ovarian Cancer Cells. Bulletin of the Korean Chemical Society 38:12, pages 1411-1414.
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Jing Li, Xiaofei Zhang, Haoyue Xiang, Linjiang Tong, Fang Feng, Hua Xie, Jian Ding & Chunhao Yang. (2017) C–H Trifluoromethylation of 2-Substituted/Unsubstituted Aminonaphthoquinones at Room Temperature with Bench-Stable (CF 3 SO 2 ) 2 Zn: Synthesis and Antiproliferative Evaluation . The Journal of Organic Chemistry 82:13, pages 6795-6800.
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Hong Li. (2016) Use of amino-naphthoquinones for production of antimicrobial textiles. Functional materials 23:3, pages 490-495.
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Dattatray Chadar, Maria Camilles, Rishikesh Patil, Ayesha Khan, Thomas Weyhermüller & Sunita Salunke-Gawali. (2015) Synthesis and characterization of n-alkylamino derivatives of vitamin K3: Molecular structure of 2-propylamino-3-methyl-1,4-naphthoquinone and antibacterial activities. Journal of Molecular Structure 1086, pages 179-189.
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Qian Zhang & Cheng-Wei Tom Chang. (2015) Divergent and facile Lewis acid-mediated synthesis of N-alkyl 2-aminomethylene-1,3-indanediones and 2-alkylamino-1,4-naphthoquinones. Tetrahedron Letters 56:7, pages 893-896.
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Rishikesh Patil, Dattatray Chadar, Dinkar Chaudhari, Justin Peter, Milind Nikalje, Thomas Weyhermüller & Sunita Salunke-Gawali. (2014) Synthesis and characterization of 2-(n-alkylamino)-1,4-napthoquinone: Molecular structures of ethyl and hexyl derivatives. Journal of Molecular Structure 1075, pages 345-351.
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Wenying Yu & Chenglong Li. (2014) Regioselective one-pot C–N coupling of substituted naphthoquinones: selective intramolecular ring fusion of sulfonamides. Tetrahedron 70:2, pages 459-464.
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L. M. Gornostaev, M. V. Vigant, O. I. Kargina, A. S. Kuznetsova, Yu. G. Khalyavina & T. I. Lavrikova. (2013) Synthesis of 2-aryl-1-hydroxy-1H-naphtho[2,3-d]imidazole-4,9-diones by reaction of 2-benzylamino-1,4-naphthoquinones with nitric acid. Russian Journal of Organic Chemistry 49:9, pages 1354-1357.
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Balasubramanian Devi Bala, Sivasubramanian Muthusaravanan & Subbu Perumal. (2013) An expedient synthesis of 1,2-dihydrobenzo[g]quinoline-5,10-diones via copper(II) triflate-catalyzed intramolecular cyclization of N-propargylaminonaphthoquinones. Tetrahedron Letters 54:29, pages 3735-3739.
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P. D. Zalavadiya, R. M. Ghetiya, B. L. Dodiya, P. B. Vekariya & H. S. Joshi. (2013) Synthesis of Some New Dihydropyrimidines by Iodine as a Catalyst at Ambient Temperature and Evaluation of Their Biological Activity. Journal of Heterocyclic Chemistry 50:4, pages 973-978.
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Huan-Ming Huang, Yu-Jin Li, Yin-Ping Dai, Wu-Bin Yu, Qin Ye & Jian-Rong Gao. (2013) Bifunctionalisation of 1,4-naphthoquinone by the Oxidative Addition of an Alkylamine and Iodine. Journal of Chemical Research 37:1, pages 34-37.
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Cinthia da S. Lisboa, Vanessa G. Santos, Boniek G. Vaz, Nanci C. de Lucas, Marcos N. Eberlin & Simon J. Garden. (2011) C−H Functionalization of 1,4-Naphthoquinone by Oxidative Coupling with Anilines in the Presence of a Catalytic Quantity of Copper(II) Acetate. The Journal of Organic Chemistry 76:13, pages 5264-5273.
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Tong-Hao Zhu, Xu Zhu, Xiao-Ping Xu, Tao Chen & Shun-Jun Ji. (2011) Ultrasound irradiation promoted catalyst-free construction of formamidine framework using isocyanide as building blocks. Tetrahedron Letters 52:21, pages 2771-2775.
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Marjan Jereb, Dejan Vražič & Marko Zupan. (2011) Iodine-catalyzed transformation of molecules containing oxygen functional groups. Tetrahedron 67:7, pages 1355-1387.
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Julio Benites, Jaime A. Valderrama, Karina Bettega, Rozangela Curi Pedrosa, Pedro Buc Calderon & Julien Verrax. (2010) Biological evaluation of donor-acceptor aminonaphthoquinones as antitumor agents. European Journal of Medicinal Chemistry 45:12, pages 6052-6057.
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Hongshe WangJune Zeng. (2009) Iodine-catalyzed efficient synthesis of chalcones by grinding under solvent-free conditions. Canadian Journal of Chemistry 87:9, pages 1209-1212.
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Jianjun Zhang & Cheng-Wei Tom Chang. (2009) One-Pot Synthesis of 1- and 2-Substituted Naphtho[2,3- d ][1,2,3]triazole-4,9-diones . The Journal of Organic Chemistry 74:11, pages 4414-4417.
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Hongshe Wang & June Zeng. (2009) Iodine catalysed synthesis of 5-(arylmethylidene)rhodanines by Grinding under Solvent-Free Conditions. Journal of Chemical Research 2009:6, pages 374-376.
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Bing Liu & Shun‐Jun Ji. (2008) ChemInform Abstract: Facile Synthesis of 2‐Amino‐1,4‐naphthoquinones Catalyzed by Molecular Iodine under Ultrasonic Irradiation.. ChemInform 39:37.
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