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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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Articles

Lewis acid-promoted synthesis of highly substituted pyrrole-fused benzoxazinones and quinoxalinones

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Pages 437-445 | Received 08 Apr 2020, Published online: 20 Oct 2020

References

  • Quesada, A. R.; Gravalos, A. R.; Puentes, J. L. F. Polyaromatic Alkaloids from Marine Invertebrates as Cytotoxic Compounds and Inhibitors of Multidrug Resistance Caused by P-Glycoprotein. Br. J. Cancer 1996, 74, 677–682. DOI: 10.1038/bjc.1996.421.
  • Demuth, H.; Breinholt, J.; Nielsen, S. E.; Gurtler, H. WO 9723486 A1, 1997.
  • Reddy, M. V. R.; Rao, M. R.; Rhodes, D.; Hansen, M. T.; Rubins, K.; Bushman, F. D.; Venkateswarlu, Y.; Faulkner, D. J. Lamellarin Alpha 20-Sulfate, an Inhibitor of HIV-1 Integrase Active against HIV-1 Virus in Cell Culture. J. Med. Chem. 1999, 42, 1901–1907. DOI: 10.1021/jm9806650.
  • Kundu, T.; Bhattacharjee, B.; Hazra, S.; Ghosh, A. K.; Bandyopadhyay, D.; Pramanik, A. Synthesis and Biological Assessment of Pyrrolobenzoxazine Scaffold as a Potent Antioxidant. J. Med. Chem. 2019, 62, 6315–6329. DOI: 10.1021/acs.jmedchem.9b00717.
  • Kurhade, S.; Kaduskar, R. D.; Dave, B.; Ramaiah, P. A.; Palle, V. P.; Bhuniy, D. Synthesis of a Novel Tetracyclic Azaindolo[2,1-c][1,4]Benzoxazine Ring System. Tetrahedron Lett. 2011, 52, 1874–1877. DOI: 10.1016/j.tetlet.2011.02.020.
  • Grande, F.; Occhiuzzi, M. A.; Ioele, G.; Ragno, G.; Garofalo, A. Benzopyrroloxazines Containing a Bridgehead Nitrogen Atom as Promising Scaffolds for the Achievement of Biologically Active Agents. Eur. J. Med. Chem. 2018, 151, 121–144. DOI: 10.1016/j.ejmech.2018.03.061.
  • Nathwani, S.-M.; Greene, L. M.; Butini, S.; Campiani, G.; Williams, D. C.; Samali, A.; Szegezdi, E.; Zisterer, D. M. The Pyrrolo-1,5-Benzoxazepine, PBOX-15, Enhances TRAIL-Induced Apoptosis by Upregulation of DR5 and Downregulation of Core Cell Survival Proteins in Acute Lymphoblastic Leukaemia Cells. Int. J. Oncol. 2016, 49, 74–88. DOI: 10.3892/ijo.2016.3518.
  • Badolato, M.; Carullo, G.; Aiello, F.; Garofalo, A. Synthesis and Experimental Validation of New PDI Inhibitors with Antiproliferative Activity. J. Chem. 2017, 2017, 1–9. DOI: 10.1155/2017/2370359.
  • Bisht, S.; Peddinti, R. K. FeCl3-Mediated Domino Reaction of Benzoxazinones with Aroylmethylidene Malonates: Synthesis to Functionalized Pyrrolobenzoxazines. J. Org. Chem. 2017, 82, 13617–13625. DOI: 10.1021/acs.joc.7b02207.
  • Snyder, D. S.; Tradtrantip, L.; Yao, C.; Kurth, M. J.; Verkman, A. S. Potent, Metabolically Stable Benzopyrimido-Pyrrolo-Oxazine-Dione (BPO) CFTR Inhibitors for Polycystic Kidney Disease. J. Med. Chem. 2011, 54, 5468–5477. DOI: 10.1021/jm200505e.
  • Demonchaux, P.; Lenoir, P.; Augert, G.; Dupassieux, P. Design of Pyrrolo-1,4-Benzoxazine Derivatives as Inhibitors of 5-Lipoxygenase and PAF Antagonists with Anthihistaminic Properties. Bioorg. Med. Chem. 1994, 4, 2383–2388. DOI: 10.1016/S0960-894X(01)80395-4.
  • Ager, I. R.; Barnes, A. C.; Danswan, G. W.; Hairsine, P. W.; Kay, D. P.; Kennewell, P. D.; Matharu, S. S.; Miller, P.; Robson, P.; Rowlands, D. A.; et al. Synthesis and Oral Antiallergic Activity of Carboxylic Acids Derived from Imidazo[2,1-c][1,4]Benzoxazines, Imidazo[1,2-a]Quinolines, Imidazo[1,2-a]Quinoxalines, Imidazo[1,2-a]Quinoxalinones, Pyrrolo[1,2-a]Quinoxalinones, Pyrrolo[2,3-a]Quinoxalinones, and Imidazo[2,1-b]Benzothiazoles. J. Med. Chem. 1988, 31, 1098–1115. DOI: 10.1021/jm00401a009.
  • Maggiolini, M.; Santolla, M. F.; Avino, S.; Aiello, F.; Rosano, C.; Garofalo, A.; Grande, F. Identification of Two Benzopyrroloxazines Acting as Selective GPER Antagonists in Breast Cancer Cells and Cancer-Associated Fibroblasts. Future Med. Chem. 2015, 7, 437–448. DOI: 10.4155/fmc.15.3.
  • Naganaboina, R. T.; Nayak, A.; Peddinti, R. K. Trifluoroacetic Acid-Promoted Michael Addition-Cyclization Reactions of Vinylogous Carbamates. Org. Biomol. Chem. 2014, 12, 3366–3370. DOI: 10.1039/c4ob00437j.
  • Moradi, L.; Piltan, M.; Rostami, H. One-Pot Synthesis of Novel Pyrrolo-1,4-Benzoxazines via a Three-Component Reaction of 2-Amino Phenols, Acetylenic Esters and Nitrostyrene Derivatives. Chin. Chem. Lett. 2014, 25, 123–126. DOI: 10.1016/j.cclet.2013.10.009.
  • Sagar, A.; Babu, V. N.; Dey, A.; Sharada, D. S. I2-Promoted Denitration Strategy: One-Pot Three Component Synthesis of Pyrrole-Fused Benzoxazines. Tetrahedron Lett. 2015, 56, 2710–2713. DOI: 10.1016/j.tetlet.2015.04.011.
  • Sharma, N.; Peddinti, R. K. Iodine-Catalyzed Regioselective Synthesis of Multisubstiuted Pyrrole Polyheterocycles Free from Rotamers and Keto-Enol Tautomers. J. Org. Chem. 2017, 82, 9360–9366. DOI: 10.1021/acs.joc.7b01538.

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