Ammonium Chloride–Catalyzed One-Pot Synthesis of Tetrahydrobenzo[α]xanthen-11-one Derivatives Under Solvent-Free Conditions

REFERENCES

• Tietze, L. F., 1996. Domino reactions in organic synthesis, Chem. Rev. 96 (1996), pp. 115–136.
   PubMed Web of Science ®Google Scholar
• Dömling, A., and Ugi, I., 2000. Multicomponent reactions with isocyanides, Angew. Chem., Int. Ed. 39 (2000), pp. 3169–3210.
   Web of Science ®Google Scholar
• Zhu, J., and Bienayme, H., 2005. Multicomponent Reactions. Germany: Weinheim; 2005.
   Google Scholar
• Weber, L., 2002. Multi-component reactions and evolutionary chemistry, Drug Discov. Today 7 (2002), pp. 143–147.
   PubMed Web of Science ®Google Scholar
• Bose, A. K., Pednekar, S., Ganguly, S. N., Chakraborty, G., and Manhas, M. S., 2004. A simplified green chemistry approach to the Biginelli reaction using “grindstone chemistry.”, Tetrahedron Lett. 45 (2004), pp. 8351–8353.
   Web of Science ®Google Scholar
• Lei, M., Wu, D.-D., Wei, H.-G., and Wang, Y.-G., 2009. Polymer-supported 4-aminoformoyldiphenylammonium triflate (PS-AFDPAT): An effective and recyclable catalyst for the Biginelli reaction, Synth. Commun. 39 (2009), pp. 475–783.
   Web of Science ®Google Scholar
• Bossio, R., Marcos, C. F., Marcaccini, S., and Pepino, R., 1997. A facile synthesis of β-lactams based on the isocyanide chemistry, Tetrahedron Lett. 38 (1997), pp. 2519–2520.
   Web of Science ®Google Scholar
• Cristau, P., Vors, J. P., and Zhu, J. P., 2001. A rapid access to biaryl ether containing macrocycles by pairwise use of Ugi 4CR and intramolecular SNAr-based cycloetherification, Org. Lett. 3 (2001), pp. 4079–4082.
   PubMed Web of Science ®Google Scholar
• Berłozecki, S., Szymanski, W., and Ostaszewski, R., 2008. Application of isocyanides derived from α-amino acids as substrates for the Ugi reaction, Synth. Commun. 38 (2008), pp. 2714–2721.
   Web of Science ®Google Scholar
• Zhao, G., Jiang, T., Gao, H., Han, B., Huang, J., and Sun, D., 2004. Mannich reaction using acidic ionic liquids as catalysts and solvents, Green Chem. 6 (2004), pp. 75–77.
   Web of Science ®Google Scholar
• Akiyama, T., and Matsuda, K.Fuchibe, K., , 2005. HCl-catalyzed stereoselective Mannich reaction in H2O–SDS system, Synlett (2005), pp. 322–324.
   Web of Science ®Google Scholar
• Poupelin, J. P., Ruf, G. S., Blanpin, O. F., Narcisse, G., Ernouf, G. U., and Lacroix, R., 1978. Synthesis and anti-inflammatory properties of bis-(2-hydroxy-1-naphthyl)methane derivatives, Eur. J. Med. Chem. 13 (1978), pp. 67–71.
   Web of Science ®Google Scholar
• Ion, R. M., Planner, A., Wiktorowicz, K., and Frackowiak, D., 1998. The incorporation of various porphyrins into blood cells measured via flow cytometry, absorption, and emission spectroscopy, Acta Biochim. Pol. 45 (1998), pp. 833–845.
   PubMed Web of Science ®Google Scholar
• Banerjee, A., and Mukherjee, A. K., 1981. Chemical aspects of santalin as a histological stain, Stain Technol. 56 (1981), pp. 83–85.
   PubMed Web of Science ®Google Scholar
• Ahmad, M., King, T. A., Ko, D.-K., Cha, B. H., and Lee, J., 2002. Performance and photostability of xanthene and pyrromethene laser dyes in sol-gel phases, J. Phys. D: Appl. Phys. 35 (2002), pp. 1473–1476.
   Web of Science ®Google Scholar
• Buehler, C. A., Cooper, D. E., and Scrudder, E. O., 1943. The stability of 2,2′-dihydroxydiphenylmethane, J. Org. Chem. 8 (1943), pp. 316–319.
   Google Scholar
• Knight, C. G., and Stephens, T., 1989. Xanthene-dye-labelled phosphatidylethanolamines as probes of interfacial pH: Studies in phospholipid vesicles, Biochem. J. 258 (1989), pp. 683–689.
   PubMed Web of Science ®Google Scholar
• Alcantara-Licudine, P. J., Kawate, M. K., and Li, Q. X., 1997. Method for the analysis of phloxine b, uranine, and related xanthene dyes in soil using supercritical fluid extraction and high-performance liquid chromatography, J. Agric. Food Chem. 45 (1997), pp. 766–773.
   Web of Science ®Google Scholar
• Knight, D. W., and Little, P. B., 1998. The first high-yielding benzyne cyclisation using a phenolic nucleophile: A new route to xanthenes, Synlett (1998), pp. 1141–1143.
   Web of Science ®Google Scholar
• Jha, A., and Beal, J., 2004. Convenient synthesis of 12H-benzo[a]xanthenes from 2-tetralone, Tetrahedron Lett. 45 (2004), pp. 8999–9001.
   Web of Science ®Google Scholar
• Van Allan, J. A., Giannini, D. D., and Whitesides, T. H., 1982. Dibenzoxanthene derivatives and related products from β-naphthol and aldehydes or acetals, J. Org. Chem. 47 (1982), pp. 820–823.
   Web of Science ®Google Scholar
• Ohishi, T., Kojima, T., Matsuoka, T., Shiro, M., and Kotsuki, H., 2001. High-yielding TfOH-catalyzed condensation of phenols with aromatic aldehydes at high pressure: A model synthesis of the benzylidene biphenol key skeleton of blepharismins, Tetrahedron Lett. 42 (2001), pp. 2493–2496.
   Web of Science ®Google Scholar
• Kuo, C. W., and Fang, J. M., 2001. Synthesis of xanthenes, indanes, and tetrahydronaphthalenes via intramolecular phenyl–carbonyl coupling reactions, Synth. Commun. 31 (2001), pp. 877–892.
   Web of Science ®Google Scholar
• Das, D., Laxminarayana, K., Krishnaiah, M., and Srinivas, Y., 2007. An efficient and convenient protocol for the synthesis of novel 12-aryl- or 12-alkyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one derivatives, Synlett (2007), pp. 3107–3112.
   Web of Science ®Google Scholar
• Li, J., Tang, W., Lu, L., and Su, W., 2008. Strontium triflate–catalyzed one-pot condensation of β-naphthol, aldehydes, and cyclic 1,3-dicarbonyl compounds, Tetrahedron Lett. 49 (2008), pp. 7117–7120.
   Web of Science ®Google Scholar
• Khurana, J. M., and Magoo, D., 2009. pTSA-catalyzed one-pot synthesis of 12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-ones in ionic liquid and neat conditions, Tetrahedron Lett. 50 (2009), pp. 4777–4780.
   Web of Science ®Google Scholar
• Kumar, A., Sharma, S., Maurya, R. A., and Sarkar, J., 2010. Diversity-oriented synthesis of benzoxanthene and benzochromene libraries via one-pot, three-component reactions and their anti-proliferative activity, J. Comb. Chem. 12 (2010), pp. 20–24.
   PubMed Web of Science ®Google Scholar
• Nandi, G. C., Samai, S., Kumar, R., and Singh, M. S., 2009. 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), pp. 7129–7134.
   Web of Science ®Google Scholar
• Wang, H.-J., Ren, X.-Q., Zhang, Y.-Y., and Zhang, Z.-H., 2009. Synthesis 12-aryl or 12-alkyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one derivatives catalyzed by dodecatungstophosphoric acid, J. Braz. Chem. Soc. 20 (2009), pp. 1939–1943.
   Web of Science ®Google Scholar
• Heravi, M. M., Alinejhad, H., and Bakhtiari, K.Oskooie, H. A., , 2010. Sulfamic acid–catalyzed solvent-free synthesis of 10-aryl-7,7-dimethyl-6,7,8,10-tetrahydro-9H-[1,3]-dioxolo[4,5-b]xanthen-9-ones and 12-aryl-9,9-dimethyl-8,9,10,12-tetrahydro-11H-benzo[α]xanthen-11-ones, Mol. Divers. 14 (2010), pp. 621–626.
   PubMed Web of Science ®Google Scholar
• Foroughifar, N., Mobinikhaledi, A., Moghanian, H., Ebrahimi, S., and Bodaghi Farad, M. A., 2008. A novel efficient four- and five-component, one-pot synthesis of 4-semicarbazonoalkyl-2-naphthols, Synlett (2008), pp. 821–826.
   Web of Science ®Google Scholar
• Foroughifar, N., Mobinikhaledi, A., and Moghanian, H., 2009. Simple and efficient method for synthesis of novel 4-substituted 1-acylthiosemicarbazides via one-pot multicomponent reactions, Synth. Commun. 39 (2009), pp. 3668–3676.
   Web of Science ®Google Scholar
• Foroughifar, N., Mobinikhaledi, A., and Moghanian, H., 2010. A straightforward and efficient catalyst-free one-pot synthesis of N-acyl-1,3-diaryl-2-azaphenalene derivatives via multicomponent reactions, Chem. Lett. 39 (2010), pp. 180–181.
   Web of Science ®Google Scholar
• Foroughifar, N., Mobinikhaledi, A., and Moghanian, H. A., 2009. A catalytic and green procedure for synthesis of 12-aryl or 12-alkyl-8,9,10,12-tetrahydrobenzo[α]xanthen-11-one derivatives under solvent-free conditions, Int. J. Green Nanotech.: Phys. Chem. 1 (2009), pp. 57–63.
   Google Scholar
• Foroughifar, N., Mobinikhaledi, A., and Moghanian, H. A., 2010. A simple and efficient procedure for the synthesis of novel 1,3-diphenyl-2-azaphenalene derivatives via one-pot multicomponent reactions, Synth. Commun. 40 (2010), pp. 1812–1821.
   Web of Science ®Google Scholar