Synthesis of 8-alkylthio- and 8-selanyl-3-tert-butylpyrazolo[5,1-c][1,2,4]triazines

References

• Cascioferro, S.; Parrino, B.; Spano, V.; Carbone, A.; Montalbano, A.; Barraja, P.; Diana, P.; Cirrincione, G. An Overview on the Recent Developments of 1,2,4-Triazine Derivatives as Anticancer Compounds. Eur. J. Med. Chem. 2017, 142, 328–375. DOI: 10.1016/j.ejmech.2017.08.009.
   PubMed Web of Science ®Google Scholar
• Ott, G. R.; Favor, D. A. Pyrrolo[2,1-f][1,2,4]Triazines: From C-Nucleosides to Kinases and Back Again, the Remarkable Journey of a Versatile Nitrogen Heterocycle. Bioorg. Med. Chem. Lett. 2017, 27, 4238–4246. DOI: 10.1016/j.bmcl.2017.07.073.
   PubMed Web of Science ®Google Scholar
• Abdel–Rahman, R. M.; Makki, M. S. T.; Ali, T. E.; Ibrahim, M. A. 1,2,4-Triazine Chemistry Part III: Synthetic Strategies to Functionalized Bridgehead Nitrogen Heteroannulated 1,2,4-Triazine Systems and their Regiospecific and Pharmacological Properties. Curr. Org. Synth. 2013, 10, 136–160. DOI: 10.2174/157017913804810933.
   Web of Science ®Google Scholar
• Hamama, W. S.; El-Bana, G. G.; Shaaban, S.; Habib, O. M. O.; Zoorob, H. H. Advances in the Domain of 4-Amino-3-Mercapto-1,2,4-Triazine-5-Ones. RSC Adv. 2016, 6, 24010–24049. DOI: 10.1039/C5RA26433B.
   Web of Science ®Google Scholar
• Rusinov, V. L.; Charushin, V. N.; Chupakhin, O. N. Biologically Active Azolo-1,2,4-Triazines and Azolopyrimidines. Russ. Chem. Bull. 2018, 67, 573–599. DOI: 10.1007/s11172-018-2113-8.
   Web of Science ®Google Scholar
• Attaby, F. A.; Elghandour, A. H. H.; Ali, M. A.; Ibrahem, Y. M. Synthesis, Reactions, and Antiviral Activity of 1-(1 H-Pyrazolo [3,4-b]Pyridin-5-yl)Ethanone and Pyrido[2′,3′:3,4]Pyrazolo[5,1-c] [1,2,4]Triazine Derivatives. Phosphorus Sulfur Silicon Relat. Elem. 2006, 181, 1087–1102. DOI: 10.1080/10426500500326404.
   Web of Science ®Google Scholar
• Britsun, V. N.; Bazavova, I. M.; Esipenko, A. N.; Lozinskii, M. O. Reaction of 4-Amino-3-Methylthio-5-Oxo-6-R-4,5-Dihydro-1,2,4-Triazines with Sulfonylacetic Acid Nitriles. Chem. Heterocycl. Compd. 2003, 39, 1623–1626. DOI: 10.1023/B:COHC.0000018340.15398.18.
   Google Scholar
• Rusinov, V. L.; Ulomskii, E. N.; Chupakhin, O. N.; Charushin, V. N. Azolo[5,1-c]-1,2,4-Triazines as a New Class of Antiviral Compounds. Russ. Chem. Bull. 2008, 57, 985–1014. DOI: 10.1007/s11172-008-0130-8.
   Web of Science ®Google Scholar
• Kristensen, J. L.; Vedsø, P.; Begtrup, M. Synthesis of Novel Azaxanthones Derived from N-Hydroxyazoles. Tetrahedron 2002, 58, 2397–2404. DOI: 10.1016/S0040-4020(02)00034-0.
   Web of Science ®Google Scholar
• Seredyuk, M.; Haukka, M.; Fritsky, I. O.; Kozłowski, H.; Krämer, R.; Pavlenko, V. A.; Gütliche, P. Bis (3,5-dimethyl-1 H-pyrazolyl) selenide–a new bidentate bent connector for preparation of 1D and 2D co-ordination polymers. Dalton Trans. 2007, 29, 3183–3194. DOI: 10.1039/B702574B.
   Google Scholar
• Ivanov, S. M.; Mironovich, L. M.; Kolotyrkina, N. G.; Shestopalov, A. M. Synthesis and Chemical Properties of 8-Lithio-4-Oxopyrazolo[5,1-c][1,2,4]Triazines. Russ. Chem. Bull. 2019, 68, 614–622. DOI: 10.1007/s11172-019-2464-9.
   Web of Science ®Google Scholar
• Ivanov, S. M.; Dmitrienko, A. O.; Medvedev, M. G.; Mironovich, L. M. Metalated Azolo[1,2,4]Triazines. II. Generation, C(4)-Substituent Dependent Stability and Electrophile Trapping of 7-Lithiopyrazolo[5,1-c][1,2,4]Triazines. J. Organomet. Chem. 2019, 896, 168–182. DOI: 10.1016/j.jorganchem.2019.06.009.
   Web of Science ®Google Scholar
• Ivanov, S. M.; Voronina, J. K.; Fakhrutdinov, A. N.; Shestopalov, A. M. Synthesis of 2-Perfluoroalkyl-1,4-Dihydropyrazolo[1,5-a][1,3,5]Triazines via Rearrangements of (1-Perfluoroacetyl-1,4-Dihydropyrazolo[5,1-c][1,2,4]Triazin-4-yl)Lithiums. J. Fluor. Chem. 2019, 220, 16–23. DOI: 10.1016/j.jfluchem.2019.02.004.
   Web of Science ®Google Scholar
• Ivanov, S. M.; Shestopalov, A. M. Metalated Azolo[1,2,4] Triazines. I. Synthesis of 2‐(6‐Tert‐Butyl‐5‐Oxo‐4,5‐Dihydro‐1,2,4‐Triazin‐3(2 H)‐Ylidene)Acetonitriles via Ring Opening Degradation of 3‐Tert‐Butyl‐7‐Lithio‐4‐Oxo‐4 H‐Pyrazolo[5,1‐c] [1,2,4]Triazin‐1‐Ides. J. Heterocyclic Chem. 2019, 56, 2210–2220. DOI: 10.1002/jhet.3615.
   Web of Science ®Google Scholar
• Ivanov, S. M.; Minyaev, M. E. Generation and Chemical Properties of (3,4-di-Tert-Butyl-1,4-Dihydropyrazolo[5,1-c][1,2,4]Triazin-4-yl)Lithiums. J. Organomet. Chem. 2020, 906, 121060. DOI: 10.1016/j.jorganchem.2019.121060.
   Web of Science ®Google Scholar
• El-Hiti, G. A.; Smith, K.; Hegazy, A. S.; Alshammari, M. B.; Masmali, A. M. Directed Lithiation of Simple Aromatics and Heterocycles for Synthesis of Substituted Derivatives. Arkivoc 2015, 2014, 19–47. DOI: 10.3998/ark.5550190.p008.744..
   Google Scholar
• Fort, Y.; Comoy, C. Lithiated Aza‐Heterocycles in Modern Synthesis. In Lithium Compounds in Organic Synthesis; Luisi, R.; Capriati, V., Eds.; Wiley–VCH: Weinheim, 2014; pp 423–462. DOI: 10.1002/9783527667512.ch15.
   Google Scholar
• Mallan, J. M.; Bebb, R. L. Metalations by Organolithium Compounds. Chem. Rev. 1969, 69, 693–755. DOI: 10.1021/cr60261a006.
   Web of Science ®Google Scholar
• Compound 5а CCDC ID: 1974467. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK. http://www.ccdc.cam.ac.uk.
   Google Scholar
• Compound 7 CCDC ID: 1957760. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK. http://www.ccdc.cam.ac.uk.
   Google Scholar
• Ivanov, S. M.; Shestopalov, A. M. Interaction of Fused 1,2,4-Triazinone with Diborane/Oxidation: A New Route for the Synthesis of Partially Saturated and Aromatic Pyrazolo[5,1-c] [1,2,4]Triazines. J. Heterocyclic Chem. 2018, 55, 2427–2433. DOI: 10.1002/jhet.3275.
   Web of Science ®Google Scholar
• Bailey, W. F.; Wachter-Jurcsak, N. t‐Butyllithium. In Encyclopedia of Reagents for Organic Synthesis; Wiley: USA, 2009; pp 1–9. DOI: 10.1002/047084289x.rb396.pub2.
   Google Scholar
• Compound 10 CCDC ID: 1957761. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK. http://www.ccdc.cam.ac.uk.
   Google Scholar
• Bruker. Apex-III; Bruker AXS Inc.: Madison, Wisconsin, USA, 2016.
   Google Scholar
• Krause, L.; Herbst-Irmer, R.; Sheldrick, G. M.; Stalke, D. Comparison of Silver and Molybdenum Microfocus X-Ray Sources for Single-Crystal Structure Determination. J. Appl. Crystallogr. 2015, 48, 3–10. DOI: 10.1107/S1600576714022985.
   PubMed Web of Science ®Google Scholar
• Sheldrick, G. M. A Short History of SHELX. Acta Crystallogr. A. Found. Crystallogr. 2008, A64, 112–122. DOI: 10.1107/S0108767307043930.
   Web of Science ®Google Scholar
• Sheldrick, G. M. Crystal Structure Refinement with SHELXL. Acta Crystallogr. A Found. Adv. 2015, A71, 3–8. DOI: 10.1107/S2053273314026370.
   Web of Science ®Google Scholar
• Sheldrick, G. M. Crystal Structure Refinement with SHELXL. Acta Crystallogr. C Struct. Chem. 2015, C71, 3–8. DOI: 10.1107/S2053229614024218.
   Web of Science ®Google Scholar
• Hamieh, A.; Chen, Y.; Abdel-Azeim, S.; Abou-Hamad, E.; Goh, S.; Samantaray, M.; Dey, R.; Cavallo, L.; Basset, J. M. Well-Defined Surface Species [(≡Si–O–)W(=O)Me 3] Prepared by Direct Methylation of [(≡Si–O–)W(=O)Cl 3], a Catalyst for Cycloalkane Metathesis and Transformation of Ethylene to Propylene. ACS Catal. 2015, 5, 2164–2171. DOI: 10.1021/cs5020749.
   Web of Science ®Google Scholar