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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 51, 2021 - Issue 3
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Synthetic Communications Reviews

Recent trends toward the synthesis of fused-benzothiazines and their derivatives

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Pages 351-378 | Received 19 Aug 2020, Published online: 12 Oct 2020

References

  • Ahmad, M.; Siddiqui, H. L.; Gardiner, J. M.; Parvez, M.; Aslam, S.; Synthesis, A.; Studies Of, N. N. Substituted Benzyl/Phenyl-2-(3,4-Dimethyl-5,5-Dioxidopyrazolo[4,3-c][1,2]Benzothiazin-2(4H)-yl)Acetamides. Med. Chem. Res. 2013, 22, 794–805. DOI: 10.1007/s00044-012-0062-6.
  • Mor, S.; Pahal, P.; Narasimhan, B. Synthesis, Characterization, Antimicrobial Activities and QSAR Studies of Some 10a-Phenylbenzo[b]Indeno[1,2-e][1,4]Thiazin-11(10aH)-Ones. Eur. J. Med. Chem. 2012, 53, 176–189. DOI: 10.1016/j.ejmech.2012.03.054.
  • Aslam, S.; Ahmad, M.; Zia-Ur-Rehman, M.; Montero, C.; Detorio, M.; Parvez, M.; Schinazi, R. F. Synthesis and anti-HIV-1 Screening of Novel N'-(1-(aryl)ethylidene)-2-(5,5-dioxido-3-phenylbenzo[e]pyrazolo[4,3-c][1,2]thiazin-4(1H)-yl)acetohydrazides. Arch. Pharm. Res. 2014, 37, 1380–1393. DOI: 10.1007/s12272-013-0200-9.
  • Aslam, S.; Zaib, S.; Ahmad, M.; Gardiner, J. M.; Ahmad, A.; Hameed, A.; Furtmann, N.; Gütschow, M.; Bajorath, J.; Iqbal, J. Novel Structural Hybrids of Pyrazolobenzothiazines with Benzimidazoles as Cholinesterase Inhibitors. Eur. J. Med. Chem. 2014, 78, 106–117. DOI: 10.1016/j.ejmech.2014.03.035.
  • Ahmad, M.; Aslam, S.; Rizvi, S. U. F.; Muddassar, M.; Ashfaq, U. A.; Montero, C.; Ollinger, O.; Detorio, M.; Gardiner, J. M.; Schinazi, R. F. Molecular Docking and anti-Viral Screening of N-Substituted Benzyl/Phenyl-2-(3,4-Dimethyl-5,5-Dioxidopyrazolo[4,3-c][1,2]Benzothiazin-2(4H)-yl)Acetamides. Bioorg. Med. Chem. Lett. 2015, 15, 1348–1351. DOI: 10.1016/j.bmcl.2015.01.007.
  • Jeleń, M.; Pluta, K.; Zimecki, M.; Morak-Młodawska, B.; Artym, J.; Kocięba, M. Synthesis and Selected Immunological Properties of Substituted Quino[3,2-b]Benzo[1,4]Thiazines. Eur. J. Med. Chem. 2013, 63, 444–456. DOI: 10.1016/j.ejmech.2013.02.023.
  • Bakavoli, M.; Sadeghian, H.; Tabatabaei, Z.; Rezaei, E.; Rahimizadeh, M.; Nikpour, M. SAR Comparative Studies on Pyrimido[4,5-b][1,4] Benzothiazine Derivatives as 15-Lipoxygenase Inhibitors, Using ab Initio Calculations. J. Mol. Model. 2008, 14, 471–478. DOI: 10.1007/s00894-008-0298-8.
  • Barazarte, A.; Lobo, G.; Gamboa, N.; Rodrigues, J. R.; Capparelli, M. V.; Alvarez-Larena, A.; López, S. E.; Charris, J. E. Synthesis and Antimalarial Activity of Pyrazolo and Pyrimido Benzothiazine Dioxide Derivatives. Eur. J. Med. Chem. 2009, 44, 1303–1310. DOI: 10.1016/j.ejmech.2008.08.005.
  • Fraga, C. A. M.; Barreiro, E. J. The Synthesis of a New Benzothiazine Derivative, Related to Oxicams, Synthesized from Natural Safrole. J. Heterocycl. Chem. 1992, 29, 1667–1669. DOI: 10.1002/jhet.5570290652.
  • Bihovsky, R.; Tao, M.; Mallamo, J. P.; Wells, G. J. 1,2-Benzothiazine 1,1-Dioxide Alpha-Ketoamide Analogues as Potent Calpain I Inhibitors. Bioorg. Med. Chem. Lett. 2004, 14, 1035–1038. DOI: 10.1016/j.bmcl.2003.11.037.
  • Bracher, F.; Berns, C. Triphosgene in Heterocyclic Chemistry: A Novel Synthesis of the anti-Inflammatory Prodrug Droxicam. J. Prakt. Chem. 1997, 339, 477–478. DOI: 10.1002/prac.19973390185.
  • Wells, G. J.; Tao, M.; Josef, K. A.; Bihovsky, R. 1,2-Benzothiazine 1,1-Dioxide P(2)-P(3) Peptide Mimetic Aldehyde Calpain I Inhibitors. J. Med. Chem. 2001, 44, 3488–3503. DOI: 10.1021/jm010178b.
  • Nikpour, M.; Mousavian, M.; Davoodnejad, M.; Alimardani, M.; Sadeghian, H. Synthesis of New Series of Pyrimido[4,5-b][1,4] Benzothiazines as 15-Lipoxygenase Inhibitors and Study of Their Inhibitory Mechanism. Med. Chem. Res. 2013, 22, 5036–5043. DOI: 10.1007/s00044-013-0506-7.
  • Ahmad, M.; Aslam, S.; Bukhari, M. H.; Montero, C.; Detorio, M.; Parvez, M.; Schinazi, R. F. Synthesis of Novel Pyrazolobenzothiazine 5,5-Dioxide Derivatives as Potent Anti-HIV-1 Agents. Med. Chem. Res. 2014, 23, 1309–1319. DOI: 10.1007/s00044-013-0718-x.
  • Mizuhara, T.; Oishi, S.; Ohno, H.; Shimura, K.; Matsuoka, M.; Fujii, N. Structure-Activity Relationship Study of Pyrimido[1,2-c][1,3]benzothiazin-6-imine Derivatives for Potent Anti-HIV Agents. Bioorg. Med. Chem. 2012, 20, 6434–6441. DOI: 10.1016/j.bmc.2012.08.030.
  • Brzozowski, Z.; Saczewski, F.; Neamati, N. Synthesis and anti-HIV-1 Activity of a Novel Series of 1,4,2-Benzodithiazine-Dioxides. Bioorg. Med. Chem. Lett. 2006, 16, 5298–5302. DOI: 10.1016/j.bmcl.2006.07.089.
  • Gouda, M. A.; Hussein, B. H. M.; Sherif, Y. E. S. Synthesis and Medicinal Importance of Oxicams and Their Analogues. Synth. Commun. 2017, 47, 1709–1736. DOI: 10.1080/00397911.2017.1350983.
  • Gouda, M. A. Overview of the Synthetic Routes of 2-Alkyl-4-Hydroxy-2H-1,2-Benzothiazine-3-Carboxamides-1,1-Dioxides (Oxicams) and Their Analogues. Synth. Commun. 2017, 47, 1527–1558. DOI: 10.1080/00397911.2017.1323102.
  • Chattopadhyay, S. K. Recent Advancement in the Synthesis of 1,2- and 2,1-Benzothiazines. Synth. Commun. 2018, 48, 3033–3078. DOI: 10.1080/00397911.2018.1527355.
  • Malathi, K.; Jeyachandran, V.; Kalaiselvan, K.; Kumar, R. R. Synthesis of Novel Dispiro 1,4-Benzothiazine Hybrid Heterocycles through 1,3-Dipolar Cycloaddition. Synth. Commun. 2015, 45, 503–512. DOI: 10.1080/00397911.2014.965329.
  • Shastri, S. L.; Chougala, B. M.; Kulkarni, M. V.; Shastri, L. A. An Efficient and Convenient Synthesis of 1, 4-Benzoxazines, 1, 4-Benzothiazines, Spiro-1, 4-Benzoxazines, and Spiro-1, 4-Benzothiazines. Synth. Commun. 2013, 43, 2464–2474. DOI: 10.1080/00397911.2012.714829.
  • Fringuelli, R.; Schiaffella, F.; Vecchiarelli, A. Antifungal and Immunomodulating Activities of 1,4-Benzothiazine Azole Derivatives: Review. J. Chemother. 2001, 13, 9–14. DOI: 10.1179/joc.2001.13.1.9.
  • Khalid, Z.; Aslam, S.; Ahmad, M.; Munawar, M. A.; Montero, C.; Detorio, M.; Parvez, M.; Schinazi, R. F. Anti-HIV Activity of New Pyrazolobenzothiazine 5,5-Dioxide-Based Acetohydrazides. Med. Chem. Res. 2015, 24, 3671–3680. DOI: 10.1007/s00044-015-1411-z.
  • Sabatini, S.; Manfroni, G.; Barreca, M. L.; Bauer, S. M.; Gargaro, M.; Cannalire, R.; Astolfi, A.; Brea, J.; Vacca, C.; Pirro, M.; et al. The Pyrazolobenzothiazine Core as a New Chemotype of p38 Alpha Mitogen-Activated Protein Kinase Inhibitors. Chem Biol Drug Des 2015, 86, 531–545. DOI: 10.1111/cbdd.12516.
  • Sajid, Z.; Ahmad, M.; Aslam, S.; Ashfaq, U. A.; Zahoor, A. F.; Saddique, F. A.; Parvez, M.; Hameed, A.; Sultan, S.; Zgou, H.; Hadda, T. B. Novel Armed Pyrazolobenzothiazine Derivatives: Synthesis, X-Ray Crystal Structure and POM Analyses of Biological Activity Against Drug Resistant Clinical Isolate of Staphylococcus Aureus. Pharm. Chem. J. 2016, 50, 172–180. DOI: 10.1007/s11094-016-1417-y.
  • Abid, S. M. A.; Aslam, S.; Zaib, S.; Bakht, S. M.; Ahmad, M.; Athar, M. M.; Gardiner, J. M.; Iqbal, J. Pyrazolobenzothiazine-Based Carbothioamides as New Structural Leads for the Inhibition of Monoamine Oxidases: Design, Synthesis, in Vitro Bioevaluation and Molecular Docking Studies. Med. Chem. Commun. 2017, 8, 452–464. DOI: 10.1039/C6MD00570E.
  • Veremeichik, Y. V.; Shurpik, D. N.; Lodochnikova, O. A.; Plemenkov, V. V. Synthesis of Benzothiazine Sulfonamides via Heteroatomic Diels–Alder Reaction of Para-fluoro-N-Sulfinylaniline with Bicyclo[2.2.1]Heptenes. Russ. J. Gen. Chem. 2016, 86, 296–299. DOI: 10.1134/S1070363216020158.
  • Tevs, O. A.; Veremeichik, Y. V.; Shurpik, D. N.; Lodochnikova, O. A.; Plemenkov, V. V. Acylated Benzothiazine sulfoneamides: Synthesis and Molecular Structure. Russ. J. Gen. Chem. 2016, 86, 1850–1853. DOI: 10.1134/S1070363216080120.
  • Tevs, O. A.; Veremeychik, Y. V.; Lodochnikova, O. A.; Plemenkov, V. V.; Litvinov, I. A. Synthesis of Hybrid Pharmacophores Based on Adducts of N-Sulfinylaniline and Norbornadiene. Russ. J. Gen. Chem. 2018, 88, 2438–2441. DOI: 10.1134/S1070363218110300.
  • Ha, T. M.; Yao, B.; Wang, Q.; Zhu, J. Sulfonamide and Tertiary Amine as Nucleophiles in Pd(II)-Catalyzed Diamination of Alkynes: Synthesis of Tetracyclic Indolobenzothiazine S,S-Dioxides. Org. Lett. 2015, 17, 5256–5259. DOI: 10.1021/acs.orglett.5b02621.
  • Ko, G. H.; Son, J. Y.; Kim, H.; Maeng, C.; Baek, Y.; Seo, B.; Um, K.; Lee, P. H. Synthesis of Indolo-1,2-Benzothiazines from Sulfoximines and 3-Diazoindolin-2-Imines. Adv. Synth. Catal. 2017, 359, 3362–3370. DOI: 10.1002/adsc.201700764.
  • Hanchate, V.; Kumar, A.; Prabhu, K. R. Synthesis of Furanone-Fused 1,2-Benzothiazine by Rh(III)-Catalyzed C–H Activation: Regioselective Oxidative Annulation Leading to in Situ Lactonization in One Pot. J. Org. Chem. 2019, 84, 11335–11342. DOI: 10.1021/acs.joc.9b01899.
  • Zhao, Q. Q.; Hu, X. Q.; Yang, M. N.; Chen, J. R.; Xiao, W. J. A Visible-Light Photocatalytic N-Radical Cascade of Hydrazones for the Synthesis of Dihydropyrazole-Fused Benzosultams. Chem. Commun. 2016, 52, 12749–12752. DOI: 10.1039/c6cc05897c.
  • Guerra, W. D.; Rossi, R. A.; Pierini, A. B.; Barolo, S. M. Synthesis of Dibenzosultams by “Transition-Metal-Free” Photoinduced Intramolecular Arylation of N-Aryl-2-halobenzenesulfonamides”. J. Org. Chem. 2016, 81, 4965–4973. DOI: 10.1021/acs.joc.6b00330.
  • Chinnagolla, R. K.; Vijeta, A.; Jeganmohan, M. Ruthenium- and Palladium-Catalyzed Consecutive Coupling and Cyclization of Aromatic Sulfoximines with Phenylboronic Acids: An Efficient Route to Dibenzothiazines. Chem. Commun. 2015, 51, 12992–12995. DOI: 10.1039/c5cc04589d.
  • Cheng, Y.; Dong, W.; Parthasarathy, K.; Bolm, C. Rhodium(III)-Catalyzed Ortho Halogenations of N-Acylsulfoximines and Synthetic Applications toward Functionalized Sulfoximine Derivatives. Org. Lett. 2017, 19, 726–729. DOI: 10.1021/acs.orglett.7b00043.
  • Zhou, H.; Chen, W.; Chen, Z. Pd/Norbornene Collaborative Catalysis on the Divergent Preparation of Heterocyclic Sulfoximine Frameworks. Org. Lett. 2018, 20, 2590–2594. DOI: 10.1021/acs.orglett.8b00776.
  • Martinez, C.; Bosnidou, A. E.; Allmendinger, S.; Muniz, K. Towards Uniform Iodine Catalysis: Intramolecular CH Amination of Arenes under Visible Light. Chem. Eur. J 2016, 22, 1–5. DOI: 10.1002/chem.201602138.
  • Ma, Y. N.; Guo, C. Y.; Zhao, Q.; Zhang, J.; Chen, X. Synthesis of Dibenzothiazines from Sulfides by One-Pot N,O-Transfer and Intramolecular C-H Amination. Green Chem. 2018, 20, 2953–2958. DOI: 10.1039/x0xx00000x.
  • Ma, Y. N.; Bian, Y.; Liu, X.; Zhang, J.; Chen, X. One-Pot Synthesis of Iodo-Dibenzothiazines from 2-Biaryl Sulfides. J. Org. Chem. 2019, 84, 450–−457. DOI: 10.1021/acs.joc.8b02729.
  • Ghandi, M.; Kia, M. A.; Sadeghzadegh, M.; Bozcheloei, A. H.; Kubicki, M. Diastereoselective Synthesis of Novel Pyrrolidine or Pyrrolizine-Fused Benzo-δ-Sultan via 1,3-Dipolar Cycloadditions. J. Heterocyclic Chem. 2015, 52, 1646–1653. DOI: 10.1002/jhet.2024.
  • Lega, D. A.; Chernykh, V. P.; Shemchuk, L. A. The Study of the Three-Component Interaction between 1-Ethyl-1H-2,1-Benzothiazin-4(3н)-One 2,2-Dioxide, Heterylcarbaldehydes and Active Methylene Nitriles. J. org. pharm. Chem. 2016, 14, 6–16. DOI: 10.24959/ophcj.16.876.
  • Lega, D. A.; Gorobets, N. Y.; Chernykh, V. P.; Shishkina, S. V.; Shemchuk, L. A. Peculiarities of 2-Amino-3-R-4-Aryl-4H-Pyranes Multicomponent Synthesis Derived from! H-2,1-Benzothiazine-4(3H)-One 2,2-Dioxide. RSC Adv. 2016, 6, 16087–16099. DOI: 10.1039/C5RA24566D.
  • Lega, D. A.; Chernykh, V. P.; Zaprutko, L.; Gzella, A. K.; Shemchuk, L. A. Synthesis of 1-Ethyl-1H-2,1-Benzothiazine 2,2-Dioxide Derivatives Using Cycloalkanecarbaldehydes and Evaluation of Their Antimicrobial Activity. Chem. Heterocycl. Comp. 2017, 53, 219–229.
  • Ahmad, S.; Jalil, S.; Zaib, S.; Aslam, S.; Ahmad, M.; Rasul, A.; Arshad, M. N.; Sultan, S.; Hameed, A.; Asiri, A. M.; Iqbal, J. Synthesis, X-Ray Crystal and Monoamine Oxidase Inhibitory Activity of 4,6-Dihydrobenzo[c]Pyrano[2,3-e][1,2]Thiazine 5,5-Dioxides: In Vitro Studies and Docking Analysis. Eur. J. Pharm. Sci. 2019, 131, 9–22. DOI: 10.1016/j.ejps.2019.02.007.
  • Lega, D. A.; Filiminova, N. I.; Dikaya, H. M.; Chernykh, V. P.; Shemchuk, L. A. In Vitro Antimicrobial Activity Evaluation of 2-Amino-3-R-6-Ethyl-4,6-Dihydropyrano[3,2-c][2,1] Benzothiazine 5,5-Dioxides with 4-Aryl Substituent and Spirofused with 2-Oxoindoline Core. Ukrainian Biopharm J. 2016, 44, 24–32. UDC: 542.057:604.4:615.33:547.8.
  • Hu, W.; Zhang, S. Method for the Synthesis of Phenothiazines via a Domino Iron-Catalyzed C-S/C-N Cross-Coupling Reaction. J. Org. Chem. 2015, 80, 6128–6132. DOI: 10.1021/acs.joc.5b00568.
  • Dabholkar, V. V.; Yadav, O. G.; Shinde, N. B. A, M. M. Synthesis, Characterization and Biological Studies of Novel Fused Benzothiazine Derivative by Sonication Technique. J. Chem. Bio. Phy. Sci. Sec. A. 2015, 5, 1180–1184.
  • Huang, M.; Huang, D.; Zhy, X.; Wan, Y. Copper-Catalyzed Domino Reactions for the Synthesis of Phenothiazines. Eur. J. Org. Chem. 2015, 22, 4835–4839. DOI: 10.1002/ejoc.201500667.
  • Samzadeh-Kermani, A. Yield of Benzothiazine Derivatives and Catalysis by Heteropolyacids. J. Sulfur. Chem 2016, 37, 692–701. DOI: 10.1080/17415993.2016.1187733.
  • Gu, Z. Y.; Cao, J. J.; Wang, S. Y.; Ji, S. J. The Involvement of the Trisulfur Radical Anion in Electron-Catalyzed Sulfur Insertion Reactions: Facile Synthesis of Benzothiazine Derivatives Under Transition Metal-Free Conditions. Chem. Sci. 2016, 7, 4067–4072. DOI: 10.1039/C6SC00240D.
  • Lin, Y. L.; Lu, G. P.; Wang, R. K.; Yi, W. B. Radical Route to 1,4-Benzothiazine Derivatives from 2-Aminobenzenethiols and Ketones under Transition-Metal-Free Conditions. Org. Lett. 2016, 18, 6424–6427. DOI: 10.1021/acs.orglett.6b03324.
  • Mohammadi, A.; Eshghi, H.; Bakavoli, M.; Hadizadeh, F.; Moradi, H. Synthesis of Novel 3-Substituted-5H-Benzo[5,6][1, 4]Thiazino[3,2-e] [1,2,4]Triazines and Their 15-Lipoxygenase Inhibitory Activity. J. Iran. Chem. Soc. 2016, 13, 1539–1547. DOI: 10.1007/s13738-016-0870-6.
  • Kavas, O.; Altug, C. Direct Acces to 1,4-Benzothiazine 4,4-Dioxides and 4-Oxides via a Domino Reaction. Tetrahedron. 2017, 73, 2656–2661. DOI: 10.1016/j.tet.2017.03.056.
  • Chornous, V. A.; Grozav, A. N.; Vovk, M. V. Synthesis of 3-Chloro-4H-Imidazo[5,1-c][1,4]Benzothiazines and 3-Chloro-4H-5λ6-Imidazo[5,1-c][1,4]Benzothiazine 5,5-Dioxides. Russ. J. Org. Chem. 2018, 54, 149–151. DOI: 10.1134/S1070428018010189.
  • Maslivets, A. A.; Dmitriev, M. V.; Maslivets, A. N. Synthesis of Spiro[1,4-Benzothiazine-2,2′-Pyrroles] by Reaction of Pyrrolo[1,2-c][4,1]Benzoxazepinetriones with 2-Aminobenzenethiol. Russ. J. Org. Chem. 2018, 54, 1573–1575. DOI: 10.1134/S1070428018100238.
  • Kumar, M.; Sharma, K.; Rajawat, A.; Khandelwal, S.; Samarth, R. M. Synthesis and Evaluation of Antioxidant and Radical Scavenging Activities of Quinolinobenzothiazinones. Res. Chem. Intermed. 2015, 41, 2265–2276. DOI: 10.1007/s11164-013-1344-4.
  • Sharma, K.; Khandelwal, S.; Samarth, R. M.; Kumar, M. Natural Product-Mimetic Scaffolds with Priviledge Heterocuclic Systems. Design, Synthesis and Evaluation of Antioxidant Activity of Quinazoquinobenzothiazinones. J. Heterocyclic Chem. 2016, 53, 220–228. DOI: 10.1002/jhet.2405.
  • Sheikhi-Mohammareh, S.; Shiri, A.; Bakavoli, M.; Mague, J. A Straightforward Approach for the Synthesis of Novel Derivatives of Benzo[b]Pyrazolo[5’,1’:2,3]Pyrimido[4,5-e][1,4]Thiazine. J. Heterocyclic Chem. 2016, 53, 1231–1235. DOI: 10.1002/jhet.2432.
  • Kroger, D.; Schluter, T.; Fischer, M.; Geibel, I.; Martens, J. A Three-Component Reaction toward Polyannulated Quinazolinones, Benzoxazinones, and Benzothiazinones. ACS Comb Sci. 2015, 17, 202–207. DOI: 10.1021/co500165a.
  • Baharfar, R.; Mohajer, S. Synthesis and Characterization of Immobilized Lipase on Fe3O4 Nanoparticles as Nano Biocatalyst for the Synthesis of Benzothiazepine and Spirobenzothiazine Chroman Derivatives. Catal. Lett. 2016, 146, 1729–1742. DOI: 10.1007/s10562-016-1797-3.
  • Mor, S.; Nagoria, S. Efficient and Convenient Synthesis, Characterization, and Antimicrobial Evaluation of Some New Tetracyclic 1,4-Benzothiazines. Synth. Commun. 2016, 46, 169–178. DOI: 10.1080/00397911.2015.1127383.
  • Wen, L. R.; Yuan, W. K.; Li, M. Dual Roles of β-Oxodithioesters in the Copper-Catalyzed Synthesis of Benzo[e]pyrazolo[1,5-c][1,3]thiazine Derivatives. J. Org. Chem. 2015, 80, 4942–4949. DOI: 10.1021/acs.joc.5b00288.
  • Hao, W.; Huang, J.; Jie, S.; Cai, M. A Highly Efficient Copper(I)-Catalyzed Cascade Reaction of o-Alkenylphenyl Isothiocyanates with Isocyanides Leading to 5H-Benzo[d]Imidazo[5,1-b][1,3]Thiazines. Eur. J. Org. Chem. 2015, 2015, 6655–6660. DOI: 10.1002/ejoc.201500800.
  • Stalling, T.; Pauly, J.; Kroger, D.; Martens, J. Multicomponent Reactions as Versatile Tool: Development of a Mild Approach to 1,3-Benzothiazine-2-Thiones. Tetrahedron. 2015, 71, 8290–8301. DOI: 10.1016/j.tet.2015.08.073.
  • Dang, P.; Zheng, Z.; Liang, Y. Copper-Catalyzed C(sp3)-S Bond and C(sp2)-S Bond Cross-Coupling of 2-(2-Iodobenzoyl) Substituted or 2-(2-Iodobenzyl) Substituted 1,2,3,4-Tetrahydroisoquinolines with Potassium Sulfide: Synthesis of Isoquinoline-Fused 1,3-Benzothiazine Scaffolds. J. Org. Chem. 2017, 82, 2263–2268. DOI: 10.1021/acs.joc.6b02943.
  • Saroha, M.; Khanna, G.; Khurana, J. M. Green Synthesis of Novel Naphtho[1,2-e]/Benzo[e][1,3] Thiazine Derivatives via One-Pot Three-Component Reaction Using Tetra n-Butyl Ammonium Bromide. Chem. Select. 2018, 3, 12560–11256. DOI: 10.1002/slct.201802778.
  • Ewies, E. F.; El-Hag, F. A. A. Synthesis, Reactions, and Antimicrobial Evaluations of New Benzo[e][1,3]Thiazine Derivatives. J. Heterocyclic Chem. 2020, 57, 163–172. DOI: 10.1002/jhet.3759.
  • Wolff, B.; Jansch, N.; Sugiarto, W. O.; Fruhschulz, S.; Lang, M.; Altintas, R.; Oehme, I.; Almes, F. J. M. Synthesis and Structure Activity Relationship of 1, 3-Benzo-Thiazine-2-Thiones as Selective HDAC8 Inhibitors. Eur. J. Med. Chem. 2019, 184, 111756 DOI: 10.1016/j.ejmech.2019.111756.
  • Matysiak, J.; Skrzypek, A.; Niewiadomy, A.; Karpińska, M. M.; Wietrzyk, J.; Paw, B.; Kłopotowska, D. Synthesis of 4-(4-Methylidene-4H-3,1-Benzothiazin-2-yl)Benzene-1,3-Diols and Their Antiproliferative Activity against Human Cancer Cell Lines. Russ. J. Bioorg. Chem. 2016, 42, 93–99. DOI: 10.1134/S106816201601009X.
  • Sailkhov, S. M.; Zaripov, R. R.; Latypova, L. R.; Abdrakhmanov, I. B. Intramolecular Heterocyclization of o-(1-Cycloalkenyl)Anilines. Synthesis of New 4Н-3,1-Benzoxazine and 4Н-3,1-Benzothiazine 2-Amino Derivatives. Chem. Heterocycl. Compd. 2019, 55, 660–664. DOI: 10.1007/s10593-019-02513-6.
  • Sasiambarrena, L. D.; Cánepa, A. S.; Bravo, R. D. Synthesis of Novel Dihydronaphthothiazine S,S-Dioxides by Intramolecular Sulfonylamidomethylation of 2-Naphthylmethanesulfonamides Using Amberlyst XN-1010. Tetrahedron Lett. 2015, 56, 7184–7189. DOI: 10.1016/j.tetlet.2015.11.042.

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