One-Pot Condensation Approach for Synthesis of Diverse Naphthopyranopyrimidines Utilizing Lactic Acid as Efficient and Eco-Friendly Catalyst

References

• Khurana, J. M., A. Lumb, A. Chaudhary, and B. Nand. “Synthesis and in Vitro Evaluation Of Antioxidant Activity of Diverse Naphthopyranopyrimidines, Diazaanthra[2,3-d][1,3]Dioxole −7,9-Dione and Tetrahydrobenzo[a]xanthen-11-ones.” RSC Adv. 3 (2013): 1844–54.
   Web of Science ®Google Scholar
• Radi, M., S. Schenone, and M. Botta. “Recent Highlights in the Synthesis of Highly Functionalized Pyrimidines.” Org. Biomol. Chem. 7 (2009): 2841–7.
   PubMed Web of Science ®Google Scholar
• Bedair, A. H., N. A. El-Hady, M. S. A. El-Latif, M. A. H. Fakery, and A. M. El-Agrody. “4-Hydroxycoumarin in Heterocyclic Synthesis: Part III. Synthesis of Some New Pyrano[2,3-d]Pyrimidine, 2-Substituted[1,2,4]Triazolo[1,5-c]Pyrimidine and Pyrimido[1,6-b][1,2,4]Triazine Derivatives.” II Farmaco 5 (2000): 708–14.
   Google Scholar
• Tandon, V. K., M. Vaish, S. Jain, D. S. Bhakuni, and R. C. Srimal. “Synthesis, Carbon-13 NMR and Hypotensive Action of 2, 3-Dihydro-2, 2-Dimethyl-4H-Naphtho [1, 2-b] Pyran-4-one.” Indian J. Pharm. Sci. 53 (1991): 22–3.
   Google Scholar
• Regnier, G. L., R. J. Canevari, J. C. Le Douarec, S. Holstorp, and J. Daussy. “Triphenylpropylpiperazine Derivatives as New Potent Analgetic Substances.” J. Med. Chem. 15 (1972): 295–301.
   PubMed Web of Science ®Google Scholar
• Metolcsy, G. “Studies on structure-Activity correlations and Mode of Action of Some Selected Types of Antifungal Compounds.” World Rev. Pest Control 10 (1971): 50–9.
   Google Scholar
• Mohr, S. J., M. A. Chirigos, F. S. Fuhrman, and J. W. Pryor. “Pyran Copolymer as an Effective Adjuvant to Chemotherapy Against a Murine Leukemia and Solid Tumor.” Cancer Res. 35 (1975): 3750–4.
   PubMed Web of Science ®Google Scholar
• Sugiura, K., F. A. Schmid, M. M. Schmid, and G. F. Brown. “Effect of Compounds on a Spectrum of Rat Tumors.” Cancer Chemother. Rep. Part 2 3 (1972): 231–308.
   Google Scholar
• Banzatti, C., U. Branzoli, P. P. Lovisolo, P. Melloni, and P. Salvadori. “Hypolipidemic Activity of Some Derivatives of 6H-dibenzo[b,d]Pyran.” Arzneim. Forsch. 34 (1984): 864–9.
   PubMed Web of Science ®Google Scholar
• Nawwar, G. A., F. M. Abdelrazek, and R. H. Swellam. “Cinnamoylnitrile-, Pyran-, and Pyranopyrazole-Derivatives Containing the Salicylanilide Moiety with Anticipated Molluscicidal Activity.” Arch. der Pharm. 324 (1991): 875–7.
   PubMed Web of Science ®Google Scholar
• Heckler, R. E., and G. P. Jourdan. Condensed Pyrimidine Derivatives and their use as Fungicides, Insecticides, and Miticides (European Patent EP 414386, 1991).
   Google Scholar
• Bedair, A. H., H. A. Emam, N. A. El-Hady, K. A. Ahmed, and A. M. El-Agrody. “Synthesis and Antimicrobial Activities of Novel Naphtho[2,1-b]Pyran, Pyrano[2,3-d]Pyrimidine and Pyrano[3,2-e][1,2,4]Triazolo[2,3-c]Pyrimidine Derivatives.” II Farmaco 56 (2001): 965–973.
   PubMedGoogle Scholar
• Ohira, T., and M. Yatagai. “Extractives of Abies Mariesii Masters, 2: The Efficient Extraction of maltol Using Supercritical Fluid, and its Antifungal and Plant Growth Regulation Effects.” J. Jpn. Wood Res. Soc. 39 (1993): 237.
   Google Scholar
• Patnaik, S., J. Marugan, K. Liu, W. Zheng, A. Thorsell, R. Eskay, N. Southall, M. Heilig, J. Inglese, and C. Austin. “Identification of Small Molecule Antagonists of the Neuropeptide-S Receptor (Probe Reports from the NIH Molecular Libraries Program [Internet], 2010).
   Google Scholar
• Weber, L. “The Application of Multi-Component Reactions in Drug Discovery.” Curr. Med. Chem. 9 (2002): 2085–93.
   PubMed Web of Science ®Google Scholar
• Ruijter, E., R. Scheffelaar, and R. V. Orru. “Multicomponent Reaction Design in the Quest for Molecular Complexity and Diversity.” Angew. Chem. Int. Ed. 50 (2011): 6234–46.
   PubMed Web of Science ®Google Scholar
• Anastas, P. T., and J. C. Warner. Green Chemistry: Theory and Practice (Oxford, New York: Oxford University Press. Inc, 1998).
   Google Scholar
• Umamahesh, B., M. Sathishkumar, K. N. Sundaramoorthy, and S. k. Iyer. “Metal-free, One-pot, rapid Synthesis of Tetrahydropyridines Using Acetic Acid as Solvent and Catalyst at Room Temperature.” Synth. Commun. 44 (2014): 943–53.
   Web of Science ®Google Scholar
• Khazaei, A., Moosavi-Zare, A. R., Mohammadi, Z., Zare, A., Khakyzadeh, V., and Darvishi, G. “Efficient Preparation of 9-aryl-1,8-dioxo-octahydroxanthenes Catalyzed by nano-TiO2 with high Recyclability.” RSC Adv. 3 (2013): 1323–6.
   Web of Science ®Google Scholar
• Moosavi-Zare, A. R., Z. Asgari, A. Zare, M. A. Zolfigol, and M. Shekouhy. “One Pot Synthesis of 1,2,4,5-tetrasubstituted-imidazoles Catalyzed by Trityl Chloride in Neutral Media.” RSC Adv. 4 (2014): 60636–9.
   Google Scholar
• Veisi, H., A. Aminimanesh, N. Khankhani, and R. Ghorbani-Vagheib. “Protic Ionic Liquid [TMG][Ac] as an Efficient, Homogeneous and Recyclable Catalyst for One-pot Four-component Synthesis of 2H-indazolo[2,1-b]phthalazine-triones and Dihydro-1H-pyrano[2,3-c]pyrazol −6-ones.” RSC Adv. 4 (2014): 25057–62.
   Web of Science ®Google Scholar
• Nandi, G. C., S. Samai, and M. S. Singh. “First InCl3-Catalyzed Three-Component Coupling Of Aldehydes, β-naphthol, and 6-amino-1,3-dimethyluracil to Functionalized Naphthopyranopyrimidines.” Synlett 7 (2010): 1133–7.
   Google Scholar
• Jalde, S. S., H. V. Chavan, L. K. Adsul, V. D. Dhakane, and B. P. Bandgar. “An Efficient Solvent-free Synthesis of Naphthopyranopyrimidines using Heteropolyacid as an Ecofriendly Catalyst.” Synth. React. Inorg., Metal-Org. Nano-Metal Chem. 44 (2014): 623–6.
   Web of Science ®Google Scholar
• Sajadikhah, S. S. “Al(H2PO4)3 as an Efficient and Recyclable Catalyst for the One-pot Synthesis of Naphthopyranopyrimidines.” RSC Adv. 5 (2015): 28038–43.
   Google Scholar
• Azimi, S. C. “L-Proline Catalyzed Synthesis of Naphthopyranopyrimidines Via Multicomponent Reaction.” Iran. J. Catalysis 5 (2015): 41–8.
   Web of Science ®Google Scholar
• Maghsoodlou, M. T., M. Karima, M. Lashkari, B. Adrom, and J. Aboonajmi. “A Green Protocol for One-pot Three-component Synthesis of 1-(benzothiazolylamino) Methyl-2-naphthol Catalyzed by Oxalic Acid.” J. Iran. Chem. Soc. 14 (2017): 329–35.
   Web of Science ®Google Scholar
• Salahi, S., M. T. Maghsoodlou, N. Hazeri, F. Movahedifar, R. Doostmohammadi, and M. Lashkari. “Acidic Ionic Liquid N-methyl 2-pyrrolidonium Hydrogen Sulfate as an Efficient Catalyst for the One-pot Multicomponent Preparation of 3,4,5-substituted Furan-2(5H)-ones.” Res. Chem. Intermed. 41 (2015): 6477–83.
   Web of Science ®Google Scholar
• Lashkari, M., M. T. Maghsoodlou, N. Hazeri, S. M. HabibiKhorasani, S. S. Sajadikhah, and R. Doostmohammadi. “Synthesis of Highly Functionalized Piperidines Via One-pot, Five-component Reactions in the Presence of Acetic Acid Solvent.” Synth. Commun. 43 (2013): 635–44.
   Web of Science ®Google Scholar
• Kangani, M., N. Hazeri, and M. T. Maghsoodlou. “Synthesis of Pyrrole and Furan Derivatives in the Presence of Lactic Acid as a Catalyst.” J. Saudi Chem. Soc. 21 (2017): 160–64.
   Web of Science ®Google Scholar
• Yazdani-Elah-Abadi, A., R. Mohebat, M. T Maghsoodlou, and R. Heydari. “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.” Polycycl. Aromat. Compd. (2016): 1–10.
   Web of Science ®Google Scholar
• Kumar, K. P., S. Satyanarayana, P. L. Reddy, G. Narasimhulu, N. Ravirala, and B. S. Reddy. “Iodine-catalyzed Three-component One-pot synthesis of Naphthopyranopyrimidines Under Solvent-free Conditions.” Tetrahedron Lett. 53 (2012): 1738–41.
   Web of Science ®Google Scholar
• Nandi, G. C., S. Samai, R. Kumar, and M. S. Singh “An Efficient One-pot Synthesis of Tetrahydrobenzo[a]xanthene-11-one and Diazabenzo[a]anthracene-9,11-dione Derivatives Under Solvent Free Condition.” Tetrahedron 65 (2009): 7129–34.
   Web of Science ®Google Scholar
• Sun, X. J., J. F. Zhou, and P. S. Zhao. “Molecular Iodine-catalyzed One-pot Synthesis of Tetrahydrobenzo[a]xanthene-11-one and Diazabenzo[a]anthracene-9,11-dione Derivatives Under Microwave Irradiation.” J. Heterocycl. Chem. 48 (2011): 1347–50.
   Web of Science ®Google Scholar