Basic ionic liquid [BMIM][OH] as heterogeneous catalyst mediated solvent-free Stobbe condensation applying grindstone technique for the synthesis of novel β-arylidene-β-benzoylpropionic acid derivatives

References

• J. O. Metzger, Solvent-free organic syntheses. Angew. Chem. Int. Ed. Engl, 1998, 37, 2975–2978.
   PubMed Web of Science ®Google Scholar
• F. Inam, S. Deo, N. Kadam, T. Lambat, Applications of thermal and microwave-assisted synthesis of xanthone derivative: a new methodology. Int. J. Innov. Appl. Res, 2014, 2(4), 88–96.
   Google Scholar
• T. Lambat, S. Deo, T. Deshmukh, Sulphamic acid assisted synthesis of polyhydroquinolines via Hantzsch multicomponent reaction: a green approach. J. Chem. Pharm. Res, 2014, 6(4), 888–892.
   Google Scholar
• M. S. Hoekstra, D. M. Sobieray, M. A. Schwindt, T. A. Mulhern, T. M. Grote, B. K. Huckabee, V. S. Hendrickson, L. C. Franklin, E. J. Granger, G. L. Karrick, Chemical development of CI-1008, an enantiomerically pure anticonvulsant. Org. Process Res. Dev, 1997, 1, 26–38.
   Web of Science ®Google Scholar
• B. Baghos, F. Naer, M. Ginidy, ϒ, ϒ-disubstituted itaconic acids. Part 1. The Stobbe condensation of 1-arylnaphthyl ketones with diethyl succinate. Helv. Imicaac, 1979, 62, 13.
   Web of Science ®Google Scholar
• J. Liu, N. Brooks, Stereoselective Stobbe condensation of ethyl methyl diphenylmethylenesuccinate with aromatic aldehydes. Org. Lett, 2002, 20, 3521–3524.
   Web of Science ®Google Scholar
• N. R. Elrayyes, The Stobbe condensation with pyrrolyl aldehydes – a synthesis of indole derivatives, J. Prakt. Chem. Band, 1973, 2, 295–299.
   Google Scholar
• S. Banerjee, R. Tayde, B. Sharma, Solvent free Stobbe condensation: a green approach, Indian J. Chem, 2009, 48B, 882–885.
   Google Scholar
• G. Daub, W. Johnson, The Stobbe condensation with sodium hydride. Int. J. Chem. Soc, 1948, 70, 418–419.
   Web of Science ®Google Scholar
• C. Thomas, M. Wolak, R. Birge, W. Lees, Improved synthesis of Indolyl fulgides. J. Org. Chem, 2001, 66, 1914–1918.
   PubMed Web of Science ®Google Scholar
• A. Tamboli, H. A. Bandal, H. Kim, Solvent free synthesis of cyclic ureas and urethanes by carbonylation method in the basic dicationic ionic liquid catalysts. Chem. Eng. J, 2016, 306, 826–831.
   Web of Science ®Google Scholar
• V. Muzalevskiy, A. Shastin, N. Shikhaliev, A. Magerramov, A. Teymurova, V. Nenajdenko, Ionic liquids as a reusable media for copper catalysis: green access to alkenes using catalytic olefination reaction. Tetrahedron, 2016, 72(45), 7159–7163.
   Web of Science ®Google Scholar
• P. Lu, L. Chen, Y. Zhang, Y. Yuan, L. Xu, X. Zhang, Rapid synthesis of ZSM-22 zeolites using imidazolium-based ionic liquids as OSDAs in fluoride media, Microporous Mesoporous Mater, 2016, 236, 193–201.
   Web of Science ®Google Scholar
• G. Thirupathi, M. Venkatanarayana, P. K. Dubey, K. Y. Bharathi, L-tyrosine catalyzed Knoevenagel condensation: facile synthesis of cyanoacrylonitriles cyanoacrylates and cyanoacrylamides in solvent free condition under grindstone method, Der. Pharm. Chem, 2012, 4(5), 1897–1901.
   Google Scholar
• V. Baghos, S. H. Doss', E. F. Eskander, Synthesis of potentially biologically active compounds via the Stobbe condensation. Organic Prep. Proc. Int, 1993, 25, 301–307.
   Web of Science ®Google Scholar
• T. Lambat, S. Deo, Synthesis of novel benzofluorenone derivatives and their HIV reverse transcriptase inhibitory activity. J. Chinese Adv. Mater. Soc. http://dx.doi.org/10.1080/22243682.2016.1251334.
   Google Scholar
• M. M. Coombs, S. B. Jaitly, F. E. H. Crawley, Potentially carcinogenic cyclopenta[a]phenanthrenes. Part IV.1. Synthesis of 17-ketones by the Stobbe condensation, J. Chem. Soc. C, 1970, 1, 266.
   Google Scholar
• T. Iwasaki, K. Kondo, T. Kuroda, Y. Moritani, S. Yamagata, M. Sugiura, H. Kikkawa, O. Kaminuma, K. Ikezawa, Novel selective PDE IV inhibitors as antiasthmatic agents. Synthesis and biological activities of a series of 1-aryl-2,3-bis(hydroxymethyl)naphthalene Lignans. J. Med. Chem, 1996, 39, 2696–2704.
   PubMed Web of Science ®Google Scholar
• I. R. Siddiqui, A. Srivastava, S. Shamim, A. Srivastava, M. Shireen, R. Afaf, A.H. Abumhdi, A. Srivastava, P. Rai, Microwave accelerated facile and efficient synthesis of piperido[3,4:5,6]pyrano[2,3-d] pyrimidinones catalyzed by basic ionic liquid [BMIM]OH, J. Mol. Catal. A, 2014, 382,126–135.
   Web of Science ®Google Scholar
• J. Yu, H. Wang, Green synthesis of pyrano[2,3-d]-pyrimidine derivatives in ionic liquids, Synth. Commun, 2005, 35, 3133–3140.
   Web of Science ®Google Scholar
• B. Ranu, R. Jana, Ionic liquid as catalyst and reaction medium – a simple, efficient and green procedure for knoevenagel condensation of aliphatic and aromatic carbonyl compounds using a task-specific basic Ionic liquid. Eur. J. Org. Chem, 2006, 10, 3767–3770.
   Web of Science ®Google Scholar
• K. Tanaka, T. Sugino, F. Toda, Selective stobbe condensation under solvent-free conditions. Green Chem, 2000, 2, 303–304.
   Web of Science ®Google Scholar
• B.C. Ranu, S. Banerjee, Ionic liquid as catalyst and reaction medium. The dramatic influence of a task-specific ionic liquid, [bmIm]OH, in Michael addition of active methylene compounds to conjugated ketones, carboxylic esters, and nitriles. Org. Lett, 2005, 7, 3049–3052.
   PubMed Web of Science ®Google Scholar
• J. Shen, H. Wang, H. Liu, Y. Sun, Z. Liu, Brønsted acidic ionic liquids as dual catalyst and solvent for environmentally friendly synthesis of chalcones. J. Mol. Catal. A: Chem, 2008, 280,24–28.
   Web of Science ®Google Scholar
• Suresh, J. S. Sandhu, Recent advances in ionic liquids: green unconventional solvents of this century: part I. Green Chem. Lett. Rev, 2011, 4,289–310.
   Web of Science ®Google Scholar