A one-pot catalyst-free synthesis of functionalized pyrrolo[1,2-a]quinoxaline derivatives from benzene-1,2-diamine, acetylenedicarboxylates and ethyl bromopyruvate

Scholarly Works

• Litvinchuk, M. B.; Bentya, A. V.; Grozav, A. M.; Yakovychuk, N. D.; Palamar, A. O.; Saliyeva, L. M.; Slyvka, N. Y.; Shishkina, S. V.; Vovk, M. V. Synthesis, antimicrobial and antioxidant activity of novel 1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-8-carboxylic acids, esters, and amides thereof. Monatshefte für Chemie - Chemical Monthly 2023, 154, 1145–1159. doi:10.1007/s00706-023-03118-8
• Agarwal, M.; Verma, K.; Pathak, G.; Pathak, S.; Mathur, J.; Kumar, M. Advances in Isocyanide‐Based Multicomponent Synthesis of Quinoxaline Scaffolds. ChemistrySelect 2023, 8. doi:10.1002/slct.202301448
• Winant, P.; Horsten, T.; de Melo, S. M. G.; da Silva Emery, F.; Dehaen, W. A Review of the Synthetic Strategies toward Dihydropyrrolo[1,2-a]Pyrazinones. Organics 2021, 2, 118–141. doi:10.3390/org2020011
• Shmoylova, Y. Y.; Kovygin, Y. A.; Ledenyova, I. V.; Prezent, M. A.; Daeva, E. D.; Baranin, S. V.; Shikhaliev, K. S. An efficient synthesis of new polyfunctional hexahydro pyrido[1,2-a]pyrazin-1-ones. Mendeleev Communications 2021, 31, 259–261. doi:10.1016/j.mencom.2021.03.039
• Piltan, M. Syntheses of Novel Tetrasubstituted Thiophenes from Benzene-1,2-Diamines, Ethyl Bromopyruvate, Malononitrile, and Aryl Isothiocyanates. Polycyclic Aromatic Compounds 2020, 41, 2103–2109. doi:10.1080/10406638.2019.1710854
• Li, Y.; Yu, J.; Bi, Y.; Yan, G.; Huang, D. Tandem Reactions of Ynones: via Conjugate Addition of Nitrogen-, Carbon-, Oxygen-, Boron-, Silicon-, Phosphorus-, and Sulfur-Containing Nucleophiles. Advanced Synthesis & Catalysis 2019, 361, 4839–4881. doi:10.1002/adsc.201900611
• Yaremchuk, I. O.; Muzychka, L. V.; Smolii, O. B.; Kucher, O. V.; Shishkina, S. V. Synthesis of novel 1,2-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one derivatives. Tetrahedron Letters 2018, 59, 442–444. doi:10.1016/j.tetlet.2017.12.065
• Li, J.; Zhang, J.; Yang, H.; Gao, Z.; Jiang, G. A Green Aerobic Oxidative Synthesis of Pyrrolo[1,2-a]quinoxalines from Simple Alcohols without Metals and Additives. The Journal of organic chemistry 2016, 82, 765–769. doi:10.1021/acs.joc.6b02501
• Wang, M.; Liu, C.; Gu, Y. Expedient synthesis of pyrrolo[1,2-a]quinoxalines through one-pot three-component reactions of o-phenylenediamines, 2-alkoxy-2,3-dihydrofurans and ketones. Tetrahedron 2016, 72, 6854–6865. doi:10.1016/j.tet.2016.09.014
• Eften’eva, R. I.; Kushnir, O. V.; Lyavinets, O. S.; Mangalagiu, I. I.; Vovk, M. V. Synthesis of polyfunctionalized pyrido[1,2-a]pyrazines and pyrazino[1,2-a]quinolines via one-pot multicomponent reactions. Monatshefte für Chemie - Chemical Monthly 2016, 147, 2127–2133. doi:10.1007/s00706-016-1836-1
• Piltan, M. One-pot, green and efficient synthesis of pyrrolo[1,2-α]quinoxalines in water. Journal of Chemical Research 2016, 40, 410–412. doi:10.3184/174751916x14652279155994
• Kaplum, V.; Cogo, J.; Sangi, D. P.; Ueda-Nakamura, T.; Corrêa, A. G.; Nakamura, C. V. In Vitro and In Vivo Activities of 2,3-Diarylsubstituted Quinoxaline Derivatives against Leishmania amazonensis. Antimicrobial agents and chemotherapy 2016, 60, 3433–3444. doi:10.1128/aac.02582-15
• Piltan, M.; Kalantari, S. One‐Pot Synthesis of Regioselective Polysubstituted Indolizines via Three‐Component Reactions of Dialkyl Acetylendicarboxylates, Dialkylchloro Malonates, and Pyridines. Journal of Heterocyclic Chemistry 2016, 54, 743–748. doi:10.1002/jhet.2604
• Sharafi, Z.; Piltan, M. Efficient assembly of quinoxaline derivatives from benzene-1,2-diamines, dialkyl acetylenedicarboxylates and ninhydrin. Heterocyclic Communications 2016, 22, 55–57. doi:10.1515/hc-2015-0187
• Kalantari, S.; Piltan, M.; Zarei, S. A. Efficient synthesis of novel Pyrroloquinoline derivatives. Journal of the Iranian Chemical Society 2015, 13, 743–746. doi:10.1007/s13738-015-0786-6
• Piltan, M.; Yavari, I.; Moradi, L. Synthesis of functionalized 1,2-dihydroisoquinolines via one-pot reaction of isoquinoline, alkyl propiolate, and 1,3-diketones. Journal of the Iranian Chemical Society 2015, 13, 605–608. doi:10.1007/s13738-015-0771-0
• Piltan, M.; Zarei, S. A.; Saydi, H.; Kalantari, S. An Efficient One-Pot Synthesis of (1,2-Dihydro-2-Oxoquinoxaline-3-Yl)Methyl Carbamodithioate Derivatives From Benzene-1,2-Diamines, Ethyl Bromopyruvate, CS2, and Secondary Amines. Phosphorus, Sulfur, and Silicon and the Related Elements 2015, 190, 1814–1819. doi:10.1080/10426507.2015.1024785
• Zhang, Z.; Li, J.; Zhang, G.; Ma, N.; Liu, Q.; Liu, T. Iron-Catalyzed Intramolecular C(sp(2))-N Cyclization of 1-(N-Arylpyrrol-2-yl)ethanone O-Acetyl Oximes toward Pyrrolo[1,2-a]quinoxaline Derivatives. The Journal of organic chemistry 2015, 80, 6875–6884. doi:10.1021/acs.joc.5b00915
• Kumari, S.; Kishore, D.; Paliwal, S.; Chauhan, R.; Dwivedi, J.; Mishra, A. Transition metal-free one-pot synthesis of nitrogen-containing heterocycles. Molecular diversity 2015, 20, 185–232. doi:10.1007/s11030-015-9596-0
• Dhole, S.; Selvaraju, M.; Maiti, B.; Chanda, K.; Sun, C.-M. Microwave Controlled Reductive Cyclization: A Selective Synthesis of Novel Benzimidazole-alkyloxypyrrolo[1,2-a]quinoxalinones. ACS combinatorial science 2015, 17, 310–316. doi:10.1021/acscombsci.5b00010

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