One-Pot, Sequential Four-Component Synthesis of Benzo[a]chromeno[2,3-c]phenazine Derivatives Using SiO₂–SO₃H as an Efficient and Recoverable Catalyst Under Conventional Heating and Microwave Irradiation

References

• Niknam, K., N. Borazjani, R. Rashidian, and A. Jamali. “Silica‐bonded N‐propylpiperazine sodium n‐propionate as recyclable catalyst for synthesis of 4H‐pyran derivatives.” Chinese Journal of Catalysis 34 (2013): 2245–54.
   Web of Science ®Google Scholar
• Orru, R. V. A., and M. De Greef. “Recent advances in solution-phase multicomponent methodology for the synthesis of heterocyclic compounds.” Synthesis 10 (2003): 1471–99.
   Google Scholar
• Schreiber, S. L. “Target-oriented and diversity-oriented organic synthesis in drug discovery.” Science 287 (2000): 1964–69.
   PubMed Web of Science ®Google Scholar
• Weber, L. “The application of multicomponent reactions in drug discovery.” Current Medicinal Chemistry 9 (2002): 2085–93.
   PubMed Web of Science ®Google Scholar
• Akritopoulou-Zanze, I., and S. W. Djuric. “Applications of MCR-derived heterocycles in drug discovery.” Topics in Heterocyclic Chemistry 25 (2010): 231–87.
   Google Scholar
• Nefzi, A., J. M. Ostresh, and R. A. Houghten. “The current status of heterocyclic combinatorial libraries.” Chemical Reviews 97 (1997): 449–72.
   PubMed Web of Science ®Google Scholar
• Thompson, L. A. “Recent applications of polymer-supported reagents and scavengers in combinatorial, parallel, or multistep synthesis.” Current Opinion in Chemical Biology 4 (2000): 324–37.
   PubMed Web of Science ®Google Scholar
• Gawande, M. B., S. N. Shelke, R. Zboril, and R. S. Varma. “Microwave-assisted chemistry: synthetic applications for rapid assembly of nanomaterials and organics.” Accounts of Chemical Research 47 (2014): 1338–48.
   PubMed Web of Science ®Google Scholar
• Garella, D., E. Borretto, A. Di Stilo, K. Martina, G. Cravotto, and P. Cintas. “Microwave-assisted synthesis of N-heterocycles in medicinal chemistry.” Medicinal Chemistry Communication 4 (2013): 1323–43.
   Google Scholar
• Zolfigol, M. A. “Silica sulfuric acid/NaNO2 as a novel heterogeneous system for production of thionitrites and disulfides under mild conditions.” Tetrahedron 57 (2001): 9509–11.
   Web of Science ®Google Scholar
• Pore, D. M., M. S. Soudagar, and U. V. Desai. “Potassium phosphate or silica sulfuric acid catalyzed conjugate addition of thiols to a,b-unsaturated ketones at room temperature under solvent-free conditions.” Tetrahedron Letters 47 (2006): 9325–28.
   Web of Science ®Google Scholar
• Minakata, S., and M. Komatsu. “Organic reactions on silica in water.” Chemical Reviews 109 (2009): 711–24.
   PubMed Web of Science ®Google Scholar
• Salehi, P., M. A. Zolfigol, F. Shirini, and M. Baghbanzadeh. “Silica sulfuric acid and silica chloride as efficient reagents for organic reactions.” Current Organic Chemistry 10 (2006): 2171–89.
   Web of Science ®Google Scholar
• Niknam, K., D. Saberi, M. Sadegheyan, and A. Deris. “Silica-bonded S-sulfonic acid: an efficient and recyclable solid acid catalyst for the synthesis of 4,40-(arylmethylene)bis(1H-pyrazol-5-ols).” Tetrahedron Letters 51 (2010): 692–4.
   Google Scholar
• Shirini, F., M. A. Zolfigol, and K. Mohammadi. “Silica sulfuric acid as a mild and efficient reagent for the acetylation of alcohols in solution and under solvent free conditions.” Korean Chemical Society 25 (2004): 325–7.
   Web of Science ®Google Scholar
• Wu, H., Y. Shen, L. Y. Fan, Y. Wan, P. Zhang, C. F. Chen, and W. X. Wang. “Stereoselective synthesis of β-amino ketones via direct Mannich-type reaction catalyzed with silica sulfuric acid.” Tetrahedron 63 (2007): 2404–8.
   Google Scholar
• De Witte, N. V., A. O. Stoppani, and M. Dubin. “2-Phenyl-beta-lapachone can affect mitochondrial function by redox cycling mediated oxidation.” Archives of Biochemistry and Biophysics 432 (2004): 129–35.
   PubMed Web of Science ®Google Scholar
• Bloxham, J., C. P. Dell, and C. Smith. “Preparation of some new benzylidenemalononitriles by an SNAr reaction: application to naphtho[1,2-b]pyran synthesis.” Heterocycles 38 (1994): 399–08.
   Web of Science ®Google Scholar
• Ferreira, S. B., F. de Carvalho da Silva, F. A. Bezerra, M. C. Lourenço, C. R. Kaiser, A. C. Pinto, and V. F. Ferreira. “Synthesis of alpha- and beta-pyran naphthoquinones as a new class of antitubercular agents.” Archiv der Pharmazie 343 (2010): 81–90.
   Web of Science ®Google Scholar
• Bonsignore, L., G. Loy, D. Secci, and A. Calignano. “Synthesis and pharmacological activity of 2-oxo-(2H) 1-benzopyran-3-carboxamide derivatives.” European Journal of Medicinal Chemistry 28 (1993): 517–20.
   Web of Science ®Google Scholar
• Makgatho, M., R. Anderson, J. O'Sullivan, T. Egan, J. Freese, N. Cornelius, and C. Van Rensburg. “Tetramethylpiperidine‐substituted phenazines as novel anti‐plasmodial agents.” Drug Development Research 50 (2000): 195–202.
   Web of Science ®Google Scholar
• Cartwright, D., W. Chilton, and D. Benson. “Pseudomonas cepacia, strain 5.5B, a biocontrol agent of Rhizoctonia solani.” Applied Microbiology and Biotechnology 43 (1995): 211–16.
   Web of Science ®Google Scholar
• Neves-Pinto, C., V. Malta, M. Pinto, R. Santos, S. Castro, and A. J. Pinto. “Structure-activity relationships for pyrido-, imidazo-, pyrazolo-, pyrazino-, and pyrrolophenazinecarboxamides as topoisomerasetargeted anticancer agents.” Journal of Medicinal Chemistry 45 (2002): 740–3.
   PubMed Web of Science ®Google Scholar
• Muller, M., and T. Sorrell. “Inhibition of the human platelet cyclooxygenase response by the naturally occurring phenazine derivative, 1-hydroxyphenazine.” Prostaglandins 50 (1995): 301–11.
   PubMed Web of Science ®Google Scholar
• Rewcastle, G. W., W. A. Denny, and B. C. Baguley. “Potential antitumor agents. 51. Synthesis and antitumor activity of substituted phenazine-1-carboxamides.” Journal of Medicinal Chemistry 30 (1987): 843–51.
   PubMed Web of Science ®Google Scholar
• Curini, M., G. Cravotto, F. Epifano, and G. Giannone. “Chemistry and biological activity of natural and synthetic prenyloxycoumarins.” Current Medicinal Chemistry 13 (2006): 199–222.
   PubMed Web of Science ®Google Scholar
• Yu, D., M. Suzuki, L. Xie, S. L. Morris-Natschke, and K. H. Lee. “Recent progress in the development of coumarin derivatives as potent anti-HIV agents.” Medicinal Research Reviews 23 (2003): 322–45.
   PubMed Web of Science ®Google Scholar
• Tangmouo, J. G., A. L. Meli, J. Komguem, V. Kuete, F. N. Ngounou, D. Lontsi, V. P. Beng, M. I. Choudhary, and B. L. Sondengam. “Crassiflorone, a new naphthoquinone from diospyros crassiflora (Hien).” Tetrahedron Letters 47 (2006): 3067–70.
   Web of Science ®Google Scholar
• Kitamura, R. O. S., P. Romoff, M. C. M. Young, M. J. Kato, and J. H. G. Lago. “Chromenes from peperomia serpens (Sw.) Loudon (Piperaceae).” Phytochemistry 67 (2006): 2398–402.
   PubMed Web of Science ®Google Scholar
• Laursen, J. B., and J. Nielsen. “Phenazine natural products: biosynthesis, synthetic analogues, and biological activity.” Chemical Reviews 104 (2004): 1663–85.
   PubMed Web of Science ®Google Scholar
• Ellis, G. P. “Chromenes, chromanones, and chromones—Introduction.” Chemistry of Heterocyclic Compounds 31 (1977): 1–10.
   Google Scholar
• Yazdani Elah Abadi, A., M. T. Maghsoodlou, R. Heydari, and R. Mohebat. “An efficient four-component domino protocol for the rapid and green synthesis of functionalized benzo[a]pyrano[2,3-c]phenazine derivatives using caffeine as a homogeneous catalyst.” Research on Chemical Intermediates 42 (2016):1227–35.
   Web of Science ®Google Scholar
• Sajadikhah, S. S., M. T. Maghsoodlou, N. Hazeri, S. M. Habibi-Khorassani, and A. C. Willis. “One-pot five-component synthesis of highly functionalized piperidines using oxalic acid dihydrate as a homogenous catalyst.” Chinese Chemical Letters 23 (2012): 569–72.
   Web of Science ®Google Scholar
• Kangani, M., M. T. Maghsoodlou, and N. Hazeri. “Vitamin B12: An efficient type catalyst for the one-pot synthesis of 3,4,5-trisubstituted furan-2(5H)-ones and N-aryl-3-aminodihydropyrrol-2-one-4-carboxylates.” Chinese Chemical Letters 27 (2016): 66–70.
   Web of Science ®Google Scholar
• Maghsoodlou, M.T., N. Hazeri, M. Lashkari, F. Nejad Shahrokhabadi, B. Naghshbandi, M. S. Kazemi-doost, M. Rashidi, F. Mir, M. Kangani, and S. Salahi. “Saccharose as a new, natural, and highly efficient catalyst for the one-pot synthesis of 4,5-dihydropyrano[3,2-c]chromenes, 2-amino-3-cyano-4H-chromenes, 1,8-dioxodecahydroacridine, and 2-substituted benzimidazole derivatives.” Research on Chemical Intermediates 41 (2015): 6985–97.
   Web of Science ®Google Scholar
• Khurana, J. M., A. Chaudhary, A. Lumb, and B. Nand. “An expedient four-component domino protocol for the synthesis of novel benzo[a]phenazine annulated heterocycles and their photophysical studies.” Green Chemistry 14 (2012): 2321–7.
   Web of Science ®Google Scholar
• Saluja, P., A. Chaudhary, and J. M. Khurana. “Synthesis of novel fluorescent benzo[a]pyrano[2,3-c]phenazine and benzo[a]chromeno[2,3-c]phenazine derivatives via facile four-component domino protocol.” Tetrahedron Letters 55 (2014): 3431–5.
   Google Scholar
• Rajeswari, M., G. Khanna, A. Chaudhary, and J. M. Khurana. “Multicomponent domino process for the synthesis of some novel benzo[a]chromenophenazine fused ring systems using H2SO4, phosphotungstic acid, and[NMP]H2PO4.” Synthetic Communications 45 (2015): 1426–32.
   Web of Science ®Google Scholar