Reaction of 2-imino-2H-chromene-3-carboxamide with phosphorus sulfides: Synthesis of novel 2-sulfido-2,3-dihydro-4H-chromeno[2,3-d][1,3,2]diaza-phosphinines

References

• Kumar, D.; Sharma, P.; Singh, H.; Nepali, K.; Gupta, G. K.; Jain, S. K.; Ntie-Kang, F. The value of pyrans as anticancer scaffolds in medicinal chemistry. RSC Adv. 2017, 7, 36977–36999. DOI: 10.1039/c7ra05441f.
   Web of Science ®Google Scholar
• Santos, C. M. M.; Silva, A. M. S. An overview of 2-styrylchromones: natural occurrence, synthesis, reactivity and biological properties. Eur. J. Org. Chem. 2017, 3115–3133. DOI: 10.1002/ejoc.201700003.
   Web of Science ®Google Scholar
• Chitreddy, S. V.; Shanmugam, S. Solvent free-synthesis of highly functionalized 4H-chromene-3-carboxamide derivatives using cerium ammonium nitrate and their antioxidant, antibacterial and solvatochromism studies. J. Mol. Liq. 2017, 243, 494–502. DOI: 10.1016/j.molliq.2017.12.082.
   Web of Science ®Google Scholar
• Patil, S. A.; Wang, J.; Li, X. S.; Chen, J.; Jones, T. S.; Ahmed, A. H.; Patil, R.; Seibel, W. L.; Li, W.; Miller, D. D. New substituted 4H-chromenes as anticancer agents. Bioorg. Med. Chem. Lett. 2012, 22, 4458–4461. DOI: 10.1016/j.bmcl.2012.04.074.
   PubMed Web of Science ®Google Scholar
• Khaligh, N. G. Synthesis and characterization of some novel 4-arylgly-oxalchromene derivatives in the presence of a polymeric catalyst and biological evaluation against Escherichia coli. Monatsh. Chem. 2018, 149, 33–38. DOI: 10.1007/s00706-017-2059-9.
   Web of Science ®Google Scholar
• Fañanas-Mastral, M.; Feringa, B. L. Copper-catalyzed synthesis of mixed alkyl aryl phosphonates. J. Am. Chem. Soc. 2014, 136, 9894–9897. DOI: 10.1021/ja505281v.
   PubMed Web of Science ®Google Scholar
• Abdou, W. M.; Barghash, R. F.; Bekheit, M. S. Carbodiimides in the synthesis of enamino- and a-aminophosphonates as peptidomimetics of analgesic/anti-inflammatory and anticancer agents. Arch. Pharm. Chem. Life Sci. 2012, 345, 884–895. DOI: 10.1002/ardp.201200142.
   PubMed Web of Science ®Google Scholar
• Abdou, W. M.; Ganoub, N. A.; Sabry, E. Spiro- and substituted thiophenetriazaphospholes and phosphoramidates as potent antineoplastic agents: synthesis, biological evaluation, and SAR studies. Monatsh Chem. 2016, 147, 619–626. DOI: 10.1007/s00706-015-1542-4.
   Web of Science ®Google Scholar
• Wong, C. C.; Cheng, K.; Papayannis, I.; Mattheolabakis, G.; Huang, L.; Xie, G.; Ouyang, N.; Rigas, B. Phospho-NSAIDs have enhanced efficacy in mice lacking plasma carboxylesterase: implications for their clinical pharmacology. Pharm. Res. 2015, 32, 1663–1675. DOI: 10.1007/s11095-014-1565-2.
   Web of Science ®Google Scholar
• Jaiyeola, A. O.; Anand, K.; Kasumbwe, K.; Ramesh, M.; Gengan, R. M. Catalytic synthesis of α-amino chromone phosphonates and their antimicrobial, toxicity and potential HIV-1 RT inhibitors based on silico screening. J. Photochem. Photobiol. B: 2017, 166, 136–147. DOI: 10.1016/j.jphotobiol.2016.11.014.
   PubMed Web of Science ®Google Scholar
• Ali, T. E. Synthesis and antibacterial activity of some new thiadiaza/triazaphospholes, thiadiaza/triaza/tetrazaphosphinines and thiadiaza/tetraza- phosphepines containing 1,2,4-triazinone moiety. Eur. J. Med. Chem. 2009, 44, 4539–4546. DOI:10.1016/j.ejmech.2009.06.022.
   PubMed Web of Science ®Google Scholar
• Ali, T. E.; Ali, M. M.; Abdel-Kariem, S. M.; Ahmed, M. M. Reaction of 2-cyano[(4-oxo-4H-chromen-3-yl)methylidene]acetohydrazide with phosphorus reagents: Synthesis and evaluation of anticancer activities of some novel 1,2-azaphospholes, 1,2,3-diazaphospholidine, and 1,3,2-diazaphosphinanes bearing a chromone ring. Synth. Commun. 2017, 47, 1458–1470. DOI:10.1080/00397911.2017.1332224.
   Google Scholar
• Abdel-Kariem, S. M.; Ali, T. E. The reaction of phosphorus decasulfide with some hydrazides and their hydrazones: new route for construction of four-membered, five-membered, and six‐membered phosphorus heterocycles. J. Heterocycl. Chem. 2017, 54, 2916–2921. DOI: 10.1002/jhet.2902.
   Web of Science ®Google Scholar
• Ali, T. E.; Hassan, M. M. Reaction of 2-cyano-3-(4-oxo-4H-chromen-3-yl)prop-2-enamide with some phosphorus reagents: synthesis of some novel diethyl phosphonates, 1,3,2-diazaphosphinanes, 1,2,3-thiazaphosphinine and 1,2-azaphospholes bearing a chromone ring. Res. Chem. Intermed. 2018, 44, 173–189. DOI: 10.1007/s11164-017-3096-z.
   Web of Science ®Google Scholar
• Czerney, P.; Hartmann, H. Synthesis of 3-cyanocoumarines. J. Prakt. Chem. 1981, 323, 691–693. DOI: 10.1002/prac.19813230424.
   Google Scholar
• Ozturk, T.; Ertas, E.; Mert, O. Use of Lawesson’s reagent in organic syntheses. Chem. Rev. 2007, 107, 5210–5278. DOI: 10.1021/cr040650b.
   PubMed Web of Science ®Google Scholar
• Ozturk, T.; Ertas, E.; Mert, O. A Berzelius reagent, phosphorus decasulfide (P4S10), in organic syntheses. Chem. Rev. 2010, 110, 3419–3478. DOI: 10.1021/cr900243d.
   PubMed Web of Science ®Google Scholar
• Mlostoń, G.; Hamera-Fałdyga, R.; Heimgartner, H. Unexpected course of the attempted conversions of ferrocenyl(hetaryl)methanols into thiols using Lawesson′s reagent. Phosphorus Sulfur Silicon Relat. Elem. 2017, 192, 732–736. DOI: 10.1080/10426507.2017.1286491.
   Web of Science ®Google Scholar
• Mlostoń, G.; Hamera-Fałdyga, R.; Celeda, M.; Linden, A.; Heimgartner, H. The unusual influence of hetaryl groups on the direct conversion of some secondary alcohols into thiols with Lawesson’s reagent: elucidation of the reaction mechanism. J. Sulfur Chem. 2017, 38, 475–487. DOI:10.1080/17415993.2017.1313257
   Web of Science ®Google Scholar
• Bergman, J.; Pettersson, B.; Hasimbegovic, V.; Svensson, P. H. Thionations using a P4S10-pyridine complex in solvents such as acetonitrile and dimethyl sulfone. J. Org. Chem. 2011, 76, 1546–1553. DOI: 10.1021/jo101865y.
   PubMed Web of Science ®Google Scholar
• Nilov, D. B.; Granik, V. G. Synthesis and properties of benzo[b]thiopheno[2,3-d]-1,3,2λ5-diazaphosphinane-2-thione derivatives. Mendeleev Commun. 2003, 13, 78–79. DOI: 10.1070/MC2003v013n02ABEH001705.
   Web of Science ®Google Scholar
• Schiemenz, G. P. Reaction of 2-hydroxybenzaldehyde with cyanoacetamide and malononitrile. Chem. Ber. 1962, 95, 483–486. DOI: 10.1002/cber.19620950225.
   Google Scholar