Water mediated and Baker’s yeast accelerated novel synthetic protocols for tetrahydrobenzo[a]xanthene-11-ones and pyrazolo[3,4-b]quinolines

References

• Hideu, T. J. P. 56005480. Chem. Abstr. 1981, 95, 80922b.
   Google Scholar
• Knight, C. G.; Stephens, T. J. Biochem. 1989, 285, 683.
   Web of Science ®Google Scholar
• Poupelin, J. P.; Saint-Rut, G.; Fussard-Blanpin, O.; Narcisse, G.; Uchida-Ernouf, G.; Lakroix, R. Eur. J. Med. Chem. 1978, 13, 67.
   Web of Science ®Google Scholar
• Saint-Ruf, G.; Hieu, H. T.; Poupelin, J. P. Naturwissenschaften. 1975, 62, 584. DOI: 10.1007/BF01166986.
   PubMed Web of Science ®Google Scholar
• Ion, R. M. Prog. Catal. 1997, 2, 55.
   Google Scholar
• Ion, R. M.; Planner, A.; Wiktorowicz, K.; Frackowiak, D. The Incorporation of Various Porphyrins into Blood Cells Measured via Flow Cytometry, Absorption and Emission Spectroscopy. Acta. Biochim. Pol. 1998, 45, 833–845. DOI: 10.18388/abp.1998_4279.
   PubMed Web of Science ®Google Scholar
• Shchekotikhin, Y. M.; Nikolaeva, T. G. Transformations of Sym-Octahydroxanthene-1,8-Diones and 1,8-Dioxo-Sym-Octahydroxanthylium Salts in Recyclization under the Influence of Amines. Chem. Heterocycl. Compd. 2006, 42, 28–33. DOI: 10.1007/s10593-006-0042-1.
   Google Scholar
• Hilderbrand, S. A.; Weissleder, R. One-Pot Synthesis of New Symmetric and Asymmetric Xanthene Dyes. Tetrahedron Lett. 2007, 48, 4383–4385. DOI: 10.1016/j.tetlet.2007.04.088.
   PubMed Web of Science ®Google Scholar
• Pohlers, G.; Scaiano, J. C.; Sinta, R. A Novel Photometric Method for the Determination of Photoacid Generation Efficiencies Using Benzothiazole and Xanthene Dyes as Acid Sensors. Chem. Mater. 1997, 9, 3222–3230. DOI: 10.1021/cm970587p.
   Web of Science ®Google Scholar
• Kees, K. L.; Fitzgerald, J. J.; Steiner, K. E. J.; Mattes, J. F.; Mihan, B.; Tosi, T.; Mondoro, D.; McCaleb, M. L. New Potent Antihyperglycemic Agents in db/db Mice: Synthesis and Structure-Activity Relationship Studies of (4-Substituted Benzyl) (Trifluoromethyl)Pyrazoles and -Pyrazolones. J. Med. Chem. 1996, 39, 3920–3928. DOI: 10.1021/jm960444z.
   PubMed Web of Science ®Google Scholar
• Erhan, P.; Mutlu, A.; Tayfun, U.; Dilek, E. Eur. J. Med. Chem. 2001, 36, 539. PII: S0223-5234(01)01243-0/SCO.
   PubMed Web of Science ®Google Scholar
• Liu, X. H.; Cui, P.; Song, B. A.; Bhadury, P. S.; Zhu, H. L.; Wang, S. F. Synthesis, Structure and Antibacterial Activity of Novel 1-(5-Substituted-3-Substituted-4,5-Dihydropyrazol-1-yl)Ethanone Oxime Ester Derivatives. Bioorg. Med. Chem. 2008, 16, 4075–4082. DOI: 10.1016/j.bmc.2008.01.035.
   PubMed Web of Science ®Google Scholar
• Shi, A.; Nguyen, T. A.; Battina, S. K.; Rana, S.; Takemoto, D. J.; Chiang, P. K.; Hua, D. H. Synthesis and anti-Breast Cancer Activities of Substituted Quinolines. Bioorg. Med. Chem. Lett. 2008, 18, 3364–3368. DOI: 10.1016/j.bmcl.2008.04.024.
   PubMed Web of Science ®Google Scholar
• Mali, J. R.; Pratap, U. R.; Jawale, D. V.; Mane, R. A. Water-Mediated One-Pot Synthetic Route for Pyrazolo[3,4-b]Quinolines. Tetrahedron Lett. 2010, 51, 3980–3982. DOI: 10.1016/j.tetlet.2010.05.117.
   Web of Science ®Google Scholar
• Hegde, H.; Shetty, N. S. Facile One-Pot Multicomponent Synthesis of 1H-Pyrazolo[3,4-b]Quinolines Using L-Proline as a Catalyst. Chem. Heterocycl. Comp. 2017, 53, 883–886. DOI: 10.1007/s10593-017-2152-3.
   Web of Science ®Google Scholar
• Siminoff, P.; Crenshaw, R. R. Stimulation of Interferon Production in Mice and in Mouse Spleen Leukocytes by Analogues of BL-20803. Antimicrob. Agents Chemother. 1977, 11, 571–573. DOI: 10.1128/AAC.11.3.571.
   PubMed Web of Science ®Google Scholar
• Selvi, S. T.; Nadaraj, V.; Mohan, S.; Sasi, R.; Hema, M. Solvent Free Microwave Synthesis and Evaluation of Antimicrobial Activity of Pyrimido[4,5-b]- and Pyrazolo[3,4-b]Quinolines. Bioorg. Med. Chem. 2006, 14, 3896–3903. DOI: 10.1016/j.bmc.2006.01.048.
   PubMed Web of Science ®Google Scholar
• (a) Stein, R. G.; Biel, J. H.; Singh, T. Antimalarials. 4-Substituted 1H-Pyrazolo[3,4-b]Quinolines. J. Med. Chem. 1970, 13, 153–155. DOI: 10.1021/jm00295a049.
   PubMed Web of Science ®Google Scholar
  (b) Schonhaber, J.; Muller, T. J. J. Org. Biomol. Chem. 2011, 9, 6196. DOI: 10.1039/c1ob05703k.
   PubMed Web of Science ®Google Scholar
  (c) D'Souza, D. M.; Kiel, A.; Herten, D.-P.; Rominger, F.; Müller, T. J. J. Synthesis, Structure and Emission Properties of Spirocyclic Benzofuranones and Dihydroindolones: A Domino Insertion–Coupling–Isomerization– Diels–Alder Approach to Rigid Fluorophores. Chem. Eur. J. 2008, 14, 529–547. DOI: 10.1002/chem.200700759.
   PubMed Web of Science ®Google Scholar
  (d) D'Souza, D. M.; Rominger, F.; Müller, T. J. J. A Domino Sequence Consisting of Insertion, Coupling, Isomerization, and Diels-Alder Steps Yields Highly Fluorescent Spirocycles. J. Angew. Chem., Int. Ed. 2005, 44, 153–158. DOI: 10.1002/anie.200461489.
   Web of Science ®Google Scholar
• Dev, J. G.; Poornachandra, Y.; Reddy, R. K.; Kumar, N. R.; Ravikumar, N.; Swaroop, K. D.; Ranjithreddy, P.; Kumar, S. G.; Nanubolu, J. B.; Kumar, G. C.; Narsaiah, B. Synthesis of Novel Pyrazolo[3,4- b ]Quinolinyl Acetamide Analogs, Their Evaluation for Antimicrobial and Anticancer Activities, Validation by Molecular Modeling and CoMFA Analysis. Eur. J. Med. Chem. 2017, 130, 223–239. DOI: 10.1016/j.ejmech.2017.02.052.
   PubMed Web of Science ®Google Scholar
• Shinde, P. V.; Kategaonkar, A. H.; Shingate, B. B.; Shingare, M. S. Surfactant Catalyzed Convenient and Greener Synthesis of Tetrahydrobenzo[a]Xanthene-11-Ones at Ambient Temperature. J. Org. Chem. 2011, 7, 53–58. DOI: 10.3762/bjoc.7.9.
   Web of Science ®Google Scholar
• Huo, C. D.; Bao, X. Z.; Hu, D. C.; Jia, X. D.; Sun, C. G.; Wang, C. Triphenylphosphine-m-Sulfonate/Carbon Tetrabromide as an Easily Recoverable Catalyst System for the Efficient Synthesis of Xanthene and Xanthenone Derivatives under Solvent-Free Conditions. Chin. Chem. Lett. 2014, 25, 699–701. DOI: 10.1016/j.cclet.2014.01.023.
   Web of Science ®Google Scholar
• Shirini, F.; Yahyazadeh, A.; Mohammadi, K. One-Pot Synthesis of Various Xanthene Derivatives Using Ionic Liquid 1,3-Disulfonic Acid Imidazolium Hydrogen Sulfate as an Efficient and Reusable Catalyst under Solvent-Free Conditions. Chin. Chem. Lett. 2014, 25, 341–347. DOI: 10.1016/j.cclet.2013.11.016.
   Web of Science ®Google Scholar
• Foroughifar, N.; Mobinikhaledi, A.; Moghanian, H. Inter. J. Green Nano. Phy. Chem. 2009, 57. DOI: 10.1080/19430870903119887.
   Google Scholar
• Nakhaei, A.; Yadegarian, S. J. App. Chem. Res. 2017, 1, 72.
   Google Scholar
• Wang, H. J.; Ren, X. Q.; Zhang, Y. Y.; Zhang, Z. H. Synthesis 12-Aryl or 12-Alkyl-8,9,10,12-Tetrahydrobenzo[a]Xanthen-11-One Derivatives Catalyzed by Dodecatungstophosphoric Acid. J. Braz. Chem. Soc. 2009, 20, 1939–1943. DOI: 10.1590/S0103-50532009001000025.
   Web of Science ®Google Scholar
• Akbari, A.; Hosseini-Nia, A. Biological Evaluation and Simple Method for the Synthesis of Tetrahydrobenzo[a]Xanthenes-11-One Derivatives. J. Saudi Chem. Soci. 2017, 21, S7–S11. DOI: 10.1016/j.jscs.2013.09.009.
   Web of Science ®Google Scholar
• Mohammadi, R.; Eidi, E.; Ghavami, M.; Kassaee, M. Z. Chitosan Synergistically Enhanced by Successive Fe3O4 and Silver Nanoparticles as a Novel Green Catalyst in One-Pot, Three-Component Synthesis of Tetrahydrobenzo[α]Xanthene-11-Ones. J. Molec. Catal. A: Chem. 2014, 393, 309–316. DOI: 10.1016/j.molcata.2014.06.005.
   Google Scholar
• Saadatjoo, N.; Golshekan, M.; Shariati, S.; Kefayati, H.; Azizi, P. Organic/Inorganic MCM-41 Magnetite Nanocomposite as a Solid Acid Catalyst for Synthesis of Benzo[α]Xanthenone Derivatives. J. Molec. Catal. A: Chem. 2013, 377, 173–179. DOI: 10.1016/j.molcata.2013.05.007.
   Web of Science ®Google Scholar
• Dutta, A. K.; Gogoi, P.; Saikia, S.; Borah, R. N,N-Disulfo-1,1,3,3-Tetramethylguanidinium Carboxylate Ionic Liquids as Reusable Homogeneous Catalysts for Multicomponent Synthesis of Tetrahydrobenzo[ a ]Xanthene and Tetrahydrobenzo[ a ]Acridine Derivatives. J. Molec. Liq. 2017, 225, 585–591. DOI: 10.1016/j.molliq.2016.11.112.
   Web of Science ®Google Scholar
• Nemati, F.; Sabaqian, S. Nano-Fe3O4 Encapsulated-Silica Particles Bearing Sulfonic Acid Groups as an Efficient, Eco-Friendly and Magnetically Recoverable Catalyst for Synthesis of Various Xanthene Derivatives under Solvent-Free Conditions. J. Saudi. Chem. Soci. 2017, 21, S383–S393. DOI: 10.1016/j.jscs.2014.04.009.
   Web of Science ®Google Scholar
• Mirjalili, B. B. F.; Bamoniri, A.; Zamani, L. Nano-TiCl4/SiO2: An Efficient and Reusable Catalyst for the Synthesis of Tetrahydrobenzo[a]Xanthenes-11-Ones. LOC. 2012, 9, 338–343. DOI: 10.2174/157017812801264700.
   Web of Science ®Google Scholar
• Shitole, B. V.; Shitole, N. V.; Kakde, G. K. OCAIJ. 2015, 11, 283.
   Google Scholar
• Silva, D. L.; Terra, B. S.; Lage, M. R.; Ruiz, A. L. T.; Silva, G. C. C.; JoaoCarvalho, E.; Carneiro, J. W.; Martins, M. F. T.; Fernadese, S. A.; Fatima, A. D. Org. Biomol. Chem. 2015, 13, 3280. DOI: 10.1039/C4OB02611J..
   PubMed Web of Science ®Google Scholar
• Ghorbani-Vaghei, R.; Malaekehpoor, M. S. Facile One-Pot Synthesis of Tetrahydrobenzo[a]Xanthene-11-One and Aryl-14 H -Dibenzo[a.j]Xanthene. Organ. Prep. Proce. Intern 2010, 42, 494–498. DOI: 10.1080/00304948.2010.514802.
   Web of Science ®Google Scholar
• Fang, D.; Yang, J.; Cao, Y. Synthesis of 12-Aryl-8,9,10,12-Tetrahydrobenzo[a]Xanthene-11-Ones Catalyzed by Biodegradable Ionic Liquid. Res. Chem. Intermed. 2013, 39, 1745–1751. DOI : DOI: 10.1007/s11164-012-0709-4.
   Web of Science ®Google Scholar
• Shaabani, A.; Mahyari, M.; Hajishaabanha, F. The Synthesis of Xanthenes and Benzoxanthenes on Graphene Oxide and Sulfated Graphene Nanosheets in Water. Res. Chem. Intermed. 2014, 40, 2799–2810. DOI: 10.1007/s11164-013-1129-9.
   Web of Science ®Google Scholar
• Heydari, R.; Shahrekipour, F. One-Pot Synthesis of 12-Aryl-8,9,10,12-Tetrahydrobenzo[a]Xanthen-11-Ones by Using of Neutral and Efficient Organocatalysts under Solvent-Free Conditions. Res. Chem. Intermed. 2015, 41, 4581–4586. DOI: 10.1007/s11164-014-1553-5.
   Web of Science ®Google Scholar
• Taghavi-Khorasani, F.; Davoodnia, A. A Fast and Green Method for Synthesis of Tetrahydrobenzo[a]Xanthene-11-Ones Using Ce(SO4)2·4H2O as a Novel, Reusable, Heterogeneous Catalyst. Res. Chem. Intermed. 2015, 41, 2415–2425. DOI: 10.1007/s11164-013-1356-0.
   Web of Science ®Google Scholar
• Davoodnia, A.; Yadegarian, S.; Nakhaei, A.; Tavakoli-Hoseini, N. A Comparative Study of TiO2, Al2O3, and Fe3O4 Nanoparticles as Reusable Heterogeneous Catalysts in the Synthesis of Tetrahydrobenzo[a]Xanthene-11-Ones. Russ. J. Gen. Chem. 2016, 86, 2849–2854. DOI: 10.1134/S1070363216120495.
   Web of Science ®Google Scholar
• Huang, H.; Yao, Y.; Lin, Q.; Zhao, J.; Hua, C.; X, G. One-Pot Synthesis of Xanthene Derivatives Catalyzed by Fe(III) Tetranitrophthalocyanine Immobilized on Activated Carbon. Russ. J. Gen. Chem. 2016, 86, 934–938. DOI: 10.1134/S1070363216040307.
   Web of Science ®Google Scholar
• Soliman, H. A.; Khatab, T. K. New Approach for Tetrachlorosilane Promoted One-Pot, Condensation Reaction for Tetrahydrobenzo[a]Xanthene-11-Ones with Docking Validation as Aurora Kinase Inhibitor. Silicon. 2018, 10, 229–233. DOI: 10.1007/s12633-016-9421-0.
   Web of Science ®Google Scholar
• Das, B.; Laxminarayana, K.; Krishnaiah, M.; Srinivas, Y. Synlett. 2007, 20, 3107. DOI: 10.1055/s-2007-990922.
   Web of Science ®Google Scholar
• Olyaei, A.; Alidoust, M. G. Rapid and Efficient One-Pot Green Synthesis of 12-Aryl-8,9,10,12-Tetrahydrobenzo[a]Xanthene-11-Ones Using Zr-MCM-41 Catalyst. Synth. Commun. 2015, 45, 94–104. DOI: 10.1080/00397911.2014.958784.
   Web of Science ®Google Scholar
• Nandi, G. C.; Samai, S.; Kumar, R.; Singh, M. S. An Efficient One-Pot Synthesis of Tetrahydrobenzo[a]Xanthene-11-One and Diazabenzo[a]Anthracene-9,11-Dione Derivatives under Solvent Free Condition. Tetrahedron 2009, 65, 7129–7134. DOI: 10.1016/j.tet.2009.06.024.
   Web of Science ®Google Scholar
• Li, J.; Tang, W.; Lu, L.; Su, W. Strontium Triflate Catalyzed One-Pot Condensation of β-Naphthol, Aldehydes and Cyclic 1,3-Dicarbonyl Compounds. Tetrahedron Lett. 2008, 49, 7117–7120. DOI: 10.1016/j.tetlet.2008.09.129.
   Web of Science ®Google Scholar
• Khurana, J. M.; Magoo, D. 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. 2009, 50, 4777–4780. DOI: 10.1016/j.tetlet.2009.06.029.
   Web of Science ®Google Scholar
• Mohamadpour, F. Trends Green Chem. 2017, 3, 1. DOI: 10.21767/2471-9889.100020.
   Google Scholar
• Sudha, S.; Pasha, M. A. Ultrasound Assisted Synthesis of Tetrahydrobenzo[c]Xanthene-11-Ones Using CAN as Catalyst. Ultrason. Sonochem. 2012, 19, 994–998. DOI: 10.1016/j.ultsonch.2012.02.002.
   PubMed Web of Science ®Google Scholar
• Chereddy, S. S.; Rao, K. U. M.; Reddy, N. B.; Reddy, M. V. N.; Prasad, S. S.; Reddy, C. S. Catal. Sci. Technol. 2012, 2, 1382. DOI: 10.1039/c2cy20041d.
   Web of Science ®Google Scholar
• Rajendran, S. P.; Manonmani, M.; Vijayalakshmi, S. Synthiesis of Pyrazolo (3,4-b)quinolines and their 1-phenyl Derivatives. Org. Prep. Proc. Int. 1994, 26, 383–385. DOI: 10.1080/00304949409458445.
   Web of Science ®Google Scholar
• Paul, S.; Gupta, M.; Gupta, R.; Loupy, A. Microwave Assisted Solvent-Free Synthesis of Pyrazolo[3,4-b]Quinolines and Pyrazolo[3,4-c]Pyrazoles Using p-TsOH. Tetrahedron Lett. 2001, 42, 3827–3829. DOI: 10.1016/S0040-4039(01)00505-6.
   Web of Science ®Google Scholar
• Pratap, U. R.; Jawale, D. V.; Waghmare, R. A.; Lingampalle, D. L.; Mane, R. A. Synthesis of 5-Arylidene-2,4-Thiazolidinediones by Knoevenagel Condensation Catalyzed by Baker's Yeast. New J. Chem. 2011, 35, 49–51. DOI: 10.1039/C0NJ00691B.
   Web of Science ®Google Scholar
• Pratap, U. R.; Mali, J. R.; Jawale, D. V.; Mane, R. A. Bakers’ Yeast Catalyzed Synthesis of Benzothiazoles in an Organic Medium. Tetrahedron Lett. 2009, 50, 1352–1354. DOI: 10.1016/j.tetlet.2009.01.032.
   Web of Science ®Google Scholar
• Pratap, U. R.; Jawale, D. V.; Bhosle, M. R.; Mane, R. A. Saccharomyces cerevisiae Catalyzed One-Pot Three Component Synthesis of 2,3-Diaryl-4-Thiazolidinones. Tetrahedron Lett. 2011, 52, 1689–1691. DOI: 10.1016/j.tetlet.2011.01.143.
   Web of Science ®Google Scholar
• Pratap, U. R.; Jawale, D. V.; Netankar, P. D.; Mane, R. A. Baker’s Yeast Catalyzed One-Pot Three-Component Synthesis of Polyfunctionalized 4H-Pyrans. Tetrahedron Lett. 2011, 52, 5817–5819. DOI: 10.1016/j.tetlet.2011.08.135.
   Web of Science ®Google Scholar
• Pratap, U. R.; Jawale, D. V.; Londhe, B. S.; Mane, R. A. Baker's Yeast Catalyzed Synthesis of 1,4-Benzothiazines, Performed under Ultrasonication. J. Mol. Cat. B: Enzym. 2011, 68, 94–97. DOI: 10.1016/j.molcatb.2010.09.018.
   Web of Science ®Google Scholar
• Khillare, L. D.; Pratap, U. R.; Bhosle, M. R.; Dhumal, S. T.; Bhalerao, M. B.; Mane, R. A. Syntheses of Biodynamic Heterocycles: baker’s Yeast-Assisted Cyclocondensations of Organic Nucleophiles and Phenacyl Chlorides. Res. Chem. Intermed. 2017, 43, 4327–4337. DOI: 10.1007/s11164-017-2880-0.
   Web of Science ®Google Scholar
• Chavan, A. S.; Kharat, A. S.; Bhosle, M. R.; Mane, R. A. A Convenient Baker Yeast Accelerated, One-Pot Synthesis of Pentasubstituted Thiopyridines. Synth. Commun. 2017, 47, 1777–1782. DOI: 10.1080/00397911.2017.1350982.
   Web of Science ®Google Scholar
• Chavan, A. S.; Kharat, A. S.; Bhosle, M. R.; Mane, R. A. Baker’s Yeast Catalyzed One-Pot Synthesis of Bioactive 2-[Benzylidene(or Pyrazol-4-Ylmethylene)Hydrazono]-1,3-Thiazolidin-4-One-5-yl-Acetic Acids. Heter. Commun. 2018, 24, 103–107. DOI: 10.1515/hc-2017-0130.
   Web of Science ®Google Scholar
• Ebrahimipour, G.; Yaghoobi Avini, M.; Ghorbanmovahhed, M. Isolation and Characterization of Glutaminase-Free L-Asparaginase Produced by Staphylococcus sp. MGM1. Sci. Med. J. 2020, 2, 46–55. DOI: 10.28991/SciMedJ -2020-0202-1.
   Google Scholar
• Afghan, A.; Baradarani, M. M.; Joule, J. A. Arkivoc 2009, (ii), 20. and references cited there in. DOI: 10.3998/ark.5550190.0010.203.
   Web of Science ®Google Scholar