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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 51, 2021 - Issue 2
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Articles

Imidazolium ylide mediated tandem Knoevenagel–Michael–O-cyclization sequence for the synthesis of multi-substituted 4,5-dihydrofurans

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Pages 234-244 | Received 05 Aug 2020, Published online: 17 Sep 2020

References

  • (a) Dean, F. M.; Sargent, M. V. In Comprehensive Heterocyclic Chemistry, Bird, C. W., Cheeseman, G. W. H., Eds.; Pergamon Press: New York, NY, 1984; Vol. 4, Part 3, p. 531–712 Furans and their benzo derivatives. (b) Sukpondma, Y.; Rukachaisirikul, V.; Phongpaichit, S. Xanthone and Sesquiterpene Derivatives from the Fruits of Garcinia Scortechinii. J. Nat. Prod. 2005, 68, 1010–1017. DOI: 10.1021/np0580098. (c) Nihei, K. I.; Asaka, Y.; Mine, Y.; Yamada, Y.; Iigo, M.; Yanagisawa, T.; Kubo, I. J. Musidunin and Musiduol, Insect Antifeedants from Croton Jatrophoides. J. Nat. Prod. 2006, 69, 975–977. DOI: 10.1021/np060068d. (d) Tang, L.; Yu, J.; Leng, Y.; Feng, Y.; Yang, Y.; Ji, R. Synthesis and Insulin-Sensitizing Activity of a Novel Kind of Benzopyran Derivative. Bioorg. Med. Chem. Lett. 2003, 13, 3437–3440. DOI: 10.1016/S0960-894X(03)00734-0.
  • (a) Mortensen, D. S.; Rodriguez, A. L.; Carlson, K. E.; Sun, J.; Katzenellenbogen, B. S.; Katzenellenbogen, J. A. Synthesis and Biological Evaluation of a Novel Series of Furans: Ligands Selective for Estrogen Receptor Alpha. J. Med. Chem. 2001, 44, 3838–3848. DOI: 10.1021/jm010211u. (b) Dong, Y.; Shi, Q.; Liu, Y. N.; Wang, X.; Bastow, K. F.; Lee, K. H. Antitumor Agents. 266. Design, Synthesis, and Biological Evaluation of Novel 2-(Furan-2-yl)Naphthalen-1-ol Derivatives as Potent and Selective Antibreast Cancer Agents. J. Med. Chem. 2009, 52, 3586–3590. DOI: 10.1021/jm9001567. (c) Yanagita, H.; Urano, E.; Matsumoto, K.; Ichikawa, R.; Takaesu, Y.; Ogata, M.; Murakami, T.; Wu, H.; Chiba, J.; Komano, J.; Hoshino, T. Structural and Biochemical Study on the Inhibitory Activity of Derivatives of 5-Nitro-Furan-2-Carboxylic Acid for RNase H Function of HIV-1 Reverse Transcriptase. Bioorg. Med. Chem. 2011, 19, 816–825. DOI: 10.1016/j.bmc.2010.12.011.
  • (a) Yadav, M. R.; Murumkar, P. R.; Ghuge, R. B. Vicinal Diaryl-Substituted Heterocycles: A Gold Mine for the Discovery of Novel Therapeutic Agents; Elsevier Ltd.: Amsterdam, Netherlands, 2018. (b) Shin, S. S.; Byun, Y.; Lim, K. M.; Choi, J. K.; Lee, K. W.; Moh, J. H.; Kim, J. K.; Jeong, Y. S.; Kim, J. Y.; Choi, Y. H.; et al. In Vitro Structure-Activity Relationship and in Vivo Studies for a Novel Class of Cyclooxygenase-2 Inhibitors: 5-Aryl-2,2-Dialkyl-4-Phenyl-3(2H)Furanone Derivatives. J. Med. Chem. 2004, 47, 792–804. DOI: 10.1021/jm020545z. (c) Vaittinen, S. L.; Komulainen, H.; Kosma, V. M.; Julkunen, A.; Mäki-Paakkanen, J.; Jansson, K.; Vartiainen, T.; Tuomisto, J. Subchronic Toxicity of 3-Chloro-4-(Dichloromethyl)-5-Hydroxy-2(5H)-Furanone (MX) in Wistar Rats. J. Food Chem. Toxicol. 1995, 33, 1027–1037. DOI: 10.1016/0278-6915(95)00079-8. (d) Muthukaman, N.; Tambe, M.; Deshmukh, A.; Pisal, D.; Tondlekar, S.; Shaikh, M.; Sarode, N.; Kattige, V. G.; Pisat, M.; Sawant, P.; et al. Discovery of Furan and Dihydrofuran-Fused Tricyclic Benzo[d]Imidazole Derivatives as Potent and Orally Efficacious Microsomal Prostaglandin E Synthase-1 (mPGES-1) Inhibitors: Part-1. Bioorg. Med. Chem. Lett. 2017, 27, 5131–5138. DOI: 10.1016/j.bmcl.2017.10.062. (e) Song, M. Y.; Cao, C.-Y.; He, Q.-R.; Dong, Q.-M.; Li, D.; Tang, J.-J.; Gao, J.-M. Constructing Novel Dihydrofuran and Dihydroisoxazole Analogues of Isocombretastatin-4 as Tubulin Polymerization Inhibitors through [3 + 2] Reactions. Bioorg. Med. Chem. 2017, 25, 5290–5302. DOI: 10.1016/j.bmc.2017.07.048.
  • (a) Gottlieb, O. R. New Natural Products and Plant Drugs with Pharmacological, Biological, or Therapeutical Activity; Springer-Verlag: Berlin, Heidelberg, Germany, 1987; p. 227. (b) Ward, R. S. Asymmetric Synthesis of Lignans. Tetrahedron 1990, 46, 5029–5041. DOI: 10.1016/S0040-4020(01)87810-8. (c) Fraga, B. M. Natural Sesquiterpenoids. Nat. Prod. Rep. 1992, 9, 217–241. DOI: 10.1039/np9920900217. (d) Merrit, A. T.; Ley, S. V. Clerodane Diterpenoids. Nat. Prod. Rep. 1992, 9, 243–287. DOI: 10.1039/np9920900243.
  • (a) Chu, P.-S.; Lopez, M. I.; Abraham, A.; El Said, K. R.; Plakas, S. M. Residue Depletion of Nitrofuran Drugs and Their Tissue-Bound Metabolites in Channel Catfish (Ictalurus Punctatus) after Oral Dosing. J. Agric. Food Chem. 2008, 56, 8030–8034. DOI: 10.1021/jf801398p. (b) Vass, M.; Hruska, K.; Franek, M. Nitrofuran Antibiotics: A Review on the Application, Prohibition and Residual Analysis. Vet. Med. 2008, 53, 469–500. DOI: 10.17221/1979-VETMED. (c) Huttner, A.; Verhaegh, E. M.; Harbarth, S.; Muller, A. E.; Theuretzbacher, U.; Mouton, J. W. Nitrofurantoin Revisited: A Systematic Review and Meta-Analysis of Controlled Trials. J. Antimicrob. Chemother. 2015, 70, 2456–2464. DOI: 10.1093/jac/dkv147.
  • (a) Gardner, J. D.; Ciociola, A. A.; Robinson, M.; McIsaac, R. L. Determination of the Time of Onset of Action of  Ranitidine and Famotidine on Intra-Gastric Acidity. Aliment. Pharmacol. Ther. 2002, 16, 1317–1326. DOI: 10.1046/j.1365-2036.2002.01291.x. (b) Fedorowicz, Z.; van Zuuren, E. J.; Hu, N. Histamine H2-Receptor Antagonists for Urticaria. Cochrane Database of Systematic Reviews 2012, CD008596. DOI: 10.1002/14651858.CD008596.pub2.
  • (a) Jacobi, P. A.; Walker, D. G.; Odeh, I. M. A. Bis Heteroannulation. 2. Oxazole Alcohols from the Interaction of Lithiomethyl Isocyanide with Lactones. A Novel Synthesis of Evodone. J. Org. Chem. 1981, 46, 2065–2069. DOI: 10.1021/jo00323a017. (b) Curran, D. P.; Singleton, D. H. Reduction of Δ2-Isoxazolines-2. A Facile Synthesis of 3(2H)-Furanones. Tetrahedron Lett. 1983, 24, 2079–2082. DOI: 10.1016/S0040-4039(00)81849-3. (c) Smith, A. B.; Guaciaro, M. A.; Schow, S. R.; Wovkulich, P. M.; Toder, B. H.; Hall, T. W. A Strategy for the Total Synthesis of Jatrophone: Synthesis of Normethyljatrophone. J. Am. Chem. Soc. 1981, 103, 219–222. DOI: 10.1021/ja00391a054. (d) Li, Y.; Hale, K. J. Asymmetric Total Synthesis and Formal Total Synthesis of the Antitumor Sesquiterpenoid (+)-Eremantholide A. Org. Lett. 2007, 9, 1267–1270. DOI: 10.1021/ol0700862.
  • (a) Yilmaz, M.; Uzunalioglu, N.; Pekel, A. T. Manganese(III) Acetate Based Oxidative Cyclizations of 3-Oxopropanenitriles with Conjugated Alkenes and Synthesis of 4,5-Dihydrofuran-3-Carbonitriles Containing Heterocycles. Tetrahedron 2005, 61, 8860–8867. DOI: 10.1016/j.tet.2005.07.019. (b) Sun, C.; Ji, S. J.; Liu, Y. Facile Synthesis of 3-(2-Furanyl)Indoles via a Multicomponent Reaction. Tetrahedron Lett. 2007, 48, 8987–8989. DOI: 10.1016/j.tetlet.2007.10.098. (c) Shang, Y.; Ju, K.; He, X.; Hu, J.; Yu, S.; Zhang, M.; Liao, K.; Wang, L.; Zhang, P. Copper-Catalyzed Multicomponent Reaction: Synthesis of 4-Arylsulfonylimino-4,5-Dihydrofuran Derivatives. J. Org. Chem. 2010, 75, 5743–5745. DOI: 10.1021/jo1010075. (d) Poonoth, M.; Krause, N. Cycloisomerization of Bifunctionalized Allenes: Synthesis of 3(2H)-Furanones in Water. J. Org. Chem. 2011, 76, 1934–1936. DOI: 10.1021/jo102416e. (e) Huynh, T. N. T.; Retailleau, P.; Denhez, C.; Nguyen, K. P. P.; Guillaume, D. Regioselective Synthesis of 3,4,5-Trisubstituted 2-Aminofurans. Org. Biomol. Chem. 2014, 12, 5098–5101. DOI: 10.1039/C4OB01037J. (f) Wei, M.-X.; Zhang, J.; Ma, F.-L.; Li, M.; Yu, J.-Y.; Luo, W.; Li, X.-Q. Synthesis and Biological Activities of Dithiocarbamates Containing 2(5H)-Furanone-Piperazine. Eur. J. Med. Chem. 2018, 155, 165–170. DOI: 10.1016/j.ejmech.2018.05.056. (g) Mandal, A.; Mandal, S. M.; Jana, S.; Bag, S. S.; Das, A. K.; Basak, A. Synthesis of Furan-Fused 1,4-Dihydrocarbazoles via an Unusual Garratt-Braverman Cyclization of Indolyl Propargyl Ethers and Their Antifungal Activity. Tetrahedron 2018, 74, 3543–3556. DOI: 10.1016/j.tet.2018.05.001. (h) Aslan, H.; Öktemer, A.; Dal, H.; Hökelek, T. Synthesis of Ferrocene Substituted Dihydrofuran Derivatives via Manganese(III) Acetate Mediated Radical Addition-Cyclization Reactions. Tetrahedron 2017, 73, 7223–7232. DOI: 10.1016/j.tet.2017.11.015. (i) Lai, Y.; Sun, L.; Sit, M. K.; Wang, Y.; Dai, W.-M. Diastereoselective Synthesis of Trans-3,5-Disubstituted Dihydrofuran-2(3H)-Ones via SmI2-Mediated Reductive Coupling of 2-Alkylacrylates of N,N-Diisopropyl-2-Hydroxybenzamide with Aldehydes. Tetrahedron 2016, 72, 664–673. DOI: 10.1016/j.tet.2015.12.009. (j) Bouhlel, A.; Curti, C.; Khoumeri, O.; Vanelle, P. Efficient One-Pot Double Buchwald–Hartwig Coupling Reaction on 5-Phenyl-4-Phenylsulfonyl-2,3-Dihydrofuran Derivatives. Tetrahedron Lett. 2011, 52, 1919–1923. DOI: 10.1016/j.tetlet.2011.02.049. (k) Tsukamoto, H.; Ito, K.; Doi, T. Synthesis of Multi-Substituted Dihydrofurans via Palladium-Catalysed Coupling between 2,3-Alkadienols and Pronucleophiles. Chem. Commun. (Camb) 2018, 54, 5102–5105. DOI: 10.1039/C8CC02589D.
  • Limprich, H. Ueber das Tetraphenol, C4H4O Ber. Dtsch. Chem. Ges.  1870, 3, 90–91. DOI: 10.1002/cber.18700030129.
  • (a) Xue, S.; He, L.; Liu, Y.-K.; Han, K. Z.; Guo, Q.-X. An Efficient CuI-Promoted Synthesis of Tri- and Tetrasubstituted Alkenes Using Organozinc Species. Synthesis 2006, 2006, 666–674. DOI: 10.1055/s-2006-926299. (b) Wang, Q.-F.; Hou, H.; Hui, L.; Yan, C.-G. Diastereoselective Synthesis of Trans-2,3-Dihydrofurans with Pyridinium Ylide Assisted Tandem Reaction. J. Org. Chem. 2009, 74, 7403–7406. DOI: 10.1021/jo901379h. (c) Chuang, C.-P.; Tsai, A.-I. Pyridinium Ylides in the Synthesis of 2,3-Dihydrofurans. Synthesis 2006, 2006, 675–679. DOI: 10.1055/s-2006-926300. (d) Rajesh, S. M.; Perumal, S.; Menendez, J. C.; Pandian, S.; Murugesan, R. Facile Ionic Liquid-Mediated, Three-Component Sequential Reactions for the Green, Regio- and Diastereoselective Synthesis of Furocoumarins. Tetrahedron 2012, 68, 5631–5636. DOI: 10.1016/j.tet.2012.04.058. (e) Indumathi, S.; Perumal, S.; Anbananthan, N. A Facile Eco-Friendly Three-Component Protocol for the Regio- and Stereoselective Synthesis of Functionalized Trans-Dihydrofuro[3,2-c]-Quinolin-4(2H)-Ones. Green Chem. 2012, 14, 3361–3367. DOI: 10.1039/c2gc36040c. (f) Kumar, A.; Srivastava, S.; Gupta, G. Cascade [4 + 1] Annulation via More Environmentally Friendly Nitrogen Ylides in Water: Synthesis of Bicyclic and Tricyclic Fused Dihydrofurans. Green Chem. 2012, 14, 3269–3272. DOI: 10.1039/c2gc36276g.
  • Kröhnke, F. Über Enol-Betaine (I. Mitteil.). Ber. dtsch. Chem. Ges. A/B. 1935, 68, 1177–1195. DOI: 10.1002/cber.19350680637.
  • (a) Banothu, J.; Basavoju, S.; Bavantula, R. Pyridinium Ylide Assisted Highly StereoselectiveOne-Pot Synthesis of Trans-2-(4-Chlorobenzoyl)-3-Aryl-Spiro[Cyclopropane-1,2′-Inden]-1′,3′-Diones and Their Antimicrobial and Nematicidal Activities. J. Heterocyclic Chem. 2015, 52, 853–860. DOI: 10.1002/jhet.2059. (b) Liu, Y.; Sun, J. W. Copper(II)-Catalyzed Synthesis of Benzo[f]Pyrido[1,2-a]Indole-6,11-Dione Derivatives via Naphthoquinone Difunctionalization Reaction. J. Org. Chem. 2012, 77, 1191–1197. DOI: 10.1021/jo301829p. (c) Shu, W. M.; Ma, J. R.; Yang, Y.; Wu, A. X. An Efficient Synthesis of Novel Fused Cycloheptatrienes through Mn(II)-Mediated Formal Intermolecular [2 + 2 + 2 + 1] Cycloaddition. Org. Lett. 2014, 16, 1286–1289. DOI: 10.1021/ol500202q. (d) Hazra, A.; Mondal, S.; Maity, A.; Naskar, S.; Saha, P.; Paira, R.; Sahu, K. B.; Paira, P.; Ghosh, S.; Sinha, C.; et al. Amberlite-IRA-402 (OH) Ion Exchange Resin Mediated Synthesis of Indolizines, Pyrrolo [1,2-a] Quinolines and Isoquinolines: Antibacterial and Antifungal Evaluation of the Products. Eur. J. Med. Chem. 2011, 46, 2132–2140. DOI: 10.1016/j.ejmech.2011.02.066. (e) Khlebnikov, A. F.; Golovkina, M. V.; Novikov, M. S.; Yufit, D. S. A Novel Strategy for the Synthesis of 3-(N-Heteryl)Pyrrole Derivatives. Org. Lett. 2012, 14, 3768–3771. DOI: 10.1021/ol3016594. (f) Liu, Y.; Hu, H. Y.; Su, X. B.; Sun, J. W.; Cao, C. S.; Shi, Y. H. One-Pot Synthesis of Pyrrolo[3,4- a ]Indolizine-1,3-Diones through [3 + 2] Cycloaddition-Oxidation Reaction Catalyzed by Cu II Salt and O 2 as the Oxidant. Eur. J. Org. Chem. 2013, 2013, 2020–2026. DOI: 10.1002/ejoc.201201488. (g) Fan, X.; Wang, Y.; He, Y.; Guo, S.; Zhang, X. Synthesis of 1,2,3-Trisubstituted Indolizines, Pyrrolo[1,2-a]Quinolines, and Pyrrolo[2,1-a]Isoquinolines from 1,2-Allenyl Ketones. Eur. J. Org. Chem. 2014, 2014, 713–717. DOI: 10.1002/ejoc.201301719. (h) Risitano, F.; Grassi, G.; Foti, F.; Bilardo, C. Pyridinium N-Ylides and (Arylmethylene)Azol-5-Ones. Reaction Cascade Leading to an Unusual Spiroisoxazolinone Ring. Tetrahedron 2000, 56, 9669–9674. DOI: 10.1016/S0040-4020(00)00921-2.
  • (a) Peixoto, D.; Figueiredo, M.; Gawande, M. B.; Corvo, M. C.; Vanhoenacker, G.; Afonso, C. A. M.; Ferreira, L. M.; Branco, P. S. Developments in the Reactivity of 2-Methylimidazolium Salts. J. Org. Chem. 2017, 82, 6232–6241. DOI: 10.1021/acs.joc.7b00807. (b) Tomashenko, O. A.; Novikov, M. S.; Khlebnikov, A. F. NHC as the Guiding Factor in a Copper-Catalyzed Intramolecular C Arylation of Pyrrolylimidazolium Salts: Synthesis of Luminescent Heterotetracyclic Frameworks. J. Org. Chem. 2017, 82, 616–623. DOI: 10.1021/acs.joc.6b02627.
  • (a) Zhong, R.; Lindhorst, A. C.; Groche, F. J.; Kuhn, F. E. Immobilization of N-Heterocyclic Carbene Compounds: A Synthetic Perspective. Chem. Rev. 2017, 117, 1970–2058. DOI: 10.1021/acs.chemrev.6b00631. (b) Benhamou, L.; Chardon, E.; Lavigne, G.; Bellemin-Laponnaz, S.; Cesar, V. Synthetic Routes to N-Heterocyclic Carbene Precursors. Chem. Rev. 2011, 111, 2705–2733. DOI: 10.1021/cr100328e. (c) Yoo, H.; Berry, D. H. Synthesis of Tridentate 2,6-Bis(Imino)Pyridyl Ruthenium(II) Complexes with N-Heterocyclic Carbene Ligands: Activation of Imidazolium Salts. Inorg. Chem. 2014, 53, 11447–11456. DOI: 10.1021/ic501248c.
  • Bara, J. E.; Carlisle, T. K.; Gabriel, C. J.; Camper, D.; Finotello, A.; Gin, D. L.; Noble, R. D. Guide to CO 2 Separations in Imidazolium-Based Room-Temperature Ionic Liquids. Ind. Eng. Chem. Res. 2009, 48, 2739–2751. DOI: 10.1021/ie8016237. (b) Shin, E.-J.; Kwon, G.-T.; Kim, S.-H. Room-Temperature Ionic Liquids (RTILs) as Green Media for Metal- and Base-Free ipso-Hydroxylation of Arylboronic Acids. Synlett. 2019, 30, 1815–1819. DOI: 10.1055/s-0037-1611894. (c) Zarei, M.; Noroozizadeh, E.; Moosavi-Zare, A. R.; Zolfigol, M. A. Synthesis of Nitroolefins and Nitroarenes under Mild Conditions. J. Org. Chem. 2018, 83, 3645–3650. DOI: 10.1021/acs.joc.7b03289. (d) Taher, A.; Lee, K. C.; Han, H. J.; Kim, D. W. Pyrene-Tagged Ionic Liquids: Separable Organic Catalysts for S N 2 Fluorination. Org. Lett. 2017, 19, 3342–3345. DOI: 10.1021/acs.orglett.7b01064.
  • (a) Hindi, K. M.; Panzner, M. J.; Tessier, C. A.; Cannon, C. L.; Youngs, W. J. The Medicinal Applications of Imidazolium Carbene-Metal Complexes. Chem. Rev. 2009, 109, 3859–3884. DOI: 10.1021/cr800500u. (b) Fei, Z.; Zhao, D.; Scopelliti, R.; Dyson, P. J. Organometallic Complexes Derived from Alkyne-Functionalized Imidazolium Salts. Organometallics 2004, 23, 1622–1628. DOI: 10.1021/om034248j. (c) Seo, H.; Kim, B. Y.; Lee, J. H.; Park, H.-J.; Son, S. U.; Chung, Y. K. Synthesis of Chiral Ferrocenyl Imidazolium Salts and Their Rhodium(I) and Iridium(I) Complexes. Organometallics 2003, 22, 4783–4791. DOI: 10.1021/om0303193. (d) Seo, H.; Park, H-J.; Kim, B. Y.; Lee, J. H.; Son, S. U.; Chung, Y. K. Synthesis of P- and S-Functionalized Chiral Imidazolium Salts and Their Rh and Ir Complexes. Organometallics 2003, 22, 618–620. DOI: 10.1021/om020878u.
  • (a) Chaudhary, S.; Milton, M. D. Dicationic Imidazolium Salts as Fluorescent Probes for Selective Detection of Fe3+ Ion in Pure Aqueous Media. J. Photochem. Photobiol. 2018, 356, 595–602. DOI: 10.1016/j.jphotochem.2018.02.003. (b) Roy, B.; Bar, A. K.; Gole, B.; Mukherjee, P. S. Fluorescent Tris-Imidazolium Sensors for Picric Acid Explosive. J. Org. Chem. 2013, 78, 1306–1310. DOI: 10.1021/jo302585a. (c) Boydston, A. J.; Vu, P. D.; Dykhno, O. L.; Chang, V.; Wyatt, A. R.; Stockett, A. S.; Ritschdorff, E. T.; Shear, J. B.; Bielawski, C. W. Modular Fluorescent Benzobis(Imidazolium) Salts: Syntheses, Photophysical Analyses, and Applications. J. Am. Chem. Soc. 2008, 130, 3143–3156. DOI: 10.1021/ja7102247. (d) Parthasarathy, A.; Pappas, H. C.; Hill, E. H.; Huang, Y.; Whitten, D. G.; Schanze, K. S. Conjugated Polyelectrolytes with Imidazolium Solubilizing Groups. Properties and Application to Photodynamic Inactivation of Bacteria. ACS Appl. Mater. Interfaces. 2015, 7, 28027–28034. DOI: 10.1021/acsami.5b02771.
  • (a) Shylaja, A.; Raja Rubina, S.; Roja, S. S.; Ranjith Kumar, R. Novel Blue Emissive Dimethylfuran Tethered 2-Aminopyridine-3-Carbonitrile as Dual Responsive Fluorescent Chemosensor for Fe3+ and Picric Acid in Nanomolar Detection Limit. Dyes Pigments 2020, 174, 108062. DOI: 10.1016/j.dyepig.2019.108062. (b) Roja, S. S.; Shylaja, A.; Ranjith Kumar, R. Phenothiazine‐Tethered 2‐Aminopyridine‐3‐Carbonitrile: Fluorescent Turn‐off Chemosensor for Fe 3+ Ions and Picric Acid. Chem. Select. 2020, 5, 2279–2283. DOI: 10.1002/slct.201904425. (c) Shylaja, A.; Roja, S. S.; Vishnu Priya, R.; Ranjith Kumar, R. Four-Component Domino Synthesis of Pyrazolo[3,4-h]Quinoline-3-Carbonitriles: “Turn-Off” Fluorescent Chemosensor for Fe3+ Ions. J. Org. Chem. 2018, 83, 14084–14090. DOI: 10.1021/acs.joc.8b01991. (d) Vivek Kumar, S.; Anusha Rani, M.; Almansour, A. I.; Suresh Kumar, R.; Athimoolam, S.; Ranjith Kumar, R. A One-Pot Access to Pyridine/Benzo Fused Cyclododecanes via Multi-Component Tandem Reactions. Tetrahedron 2018, 74, 4569–4577. DOI: 10.1016/j.tet.2018.07.020. (e) Muthu, M.; Vishnu Priya, R.; Almansour, A. I.; Suresh Kumar, R.; Ranjith Kumar, R. Synthesis of Indole-Cycloalkyl[b]Pyridine Hybrids via a Four-Component Six-Step Tandem Process. Beilstein J. Org. Chem. 2018, 14, 2907–2915. DOI: 10.3762/bjoc.14.269. (f) Maharani, S.; Vivek Kumar, S.; Almansour, A. I.; Suresh Kumar, R.; Anitha, K.; Ranjith Kumar, R. Synthesis of Penta- and Tetra-Cyclic Cage-like Compounds and Dispiro Heterocycles through Microwave-Assisted Solvent-Free Multi-Component Domino Reactions. New J. Chem. 2017, 41, 11009–11015. DOI: 10.1039/C7NJ01673E. (g) Maharani, S.; Almansour, A. I.; Suresh Kumar, R.; Arumugam, N.; Ranjith Kumar, R. Synthesis of Cycloalkano[b]Pyridines by Multicomponent Strategy: Ring-Size Mediated Product Selectivity, Substitution-Induced Axial Chirality and Influence of the 14N Quadrupole-Relaxation. Tetrahedron 2016, 72, 4582–4592. DOI: 10.1016/j.tet.2016.06.030. (h) Anusha Rani, M.; Vivek Kumar, S.; Roja, S. S.; Almansour, A. I.; Suresh Kumar, R.; Athimoolam, S.; Ranjith Kumar, R. Synthesis of Highly Functionalized 2-Thiaspiro[4.5]Deca-6,8-Dienes via Atom Efficient Tandem Michael Addition/Thorpe–Ziegler Cyclization. RSC Adv. 2016, 6, 40585–40592. DOI: 10.1039/C6RA05572A. (i) Sumesh, R. V.; Malathi, A.; Ranjith Kumar, R. A Facile Tandem Michael Addition/O-Cyclization/Elimination Route to Novel Chromeno[3,2-c]Pyridines. Mol. Divers. 2015, 19, 233–249. DOI: 10.1007/s11030-015-9576-4. (j) Maharani, S.; Ranjith Kumar, R. Domino Four-Component Synthesis of Novel Cycloocta[b]Pyridines. Tetrahedron Lett. 2015, 56, 179–181. DOI: 10.1016/j.tetlet.2014.11.052. (k) Sivakumar, S.; Ranjith Kumar, R. Domino Knoevenagel Condensation/Aza-Ene Addition/ N -Cyclization Route to Functionalized Imidazo[1,2-a]Pyridines and Pyrido[1,2-a]Pyrimidines. Asian J. Org. Chem. 2014, 3, 974–983. DOI: 10.1002/ajoc.201402100. (l) Anusha Rani, M.; Jeyachandran, V.; Muthu, M.; Sivakolunthu, S.; Ranjith Kumar, R. Microwave-Assisted Chemoselective Synthesis of Novel Pyrazolo[3,4-b]Thieno[3,4-e]Pyridines: Substitution Induced Axial Chirality. Tetrahedron Lett. 2014, 55, 5805–5807. DOI: 10.1016/j.tetlet.2014.08.112. (m) Kanchithalaivan, S.; Sumesh, R. V.; Ranjith Kumar, R. Ultrasound-Assisted Sequential Multicomponent Strategy for the Combinatorial Synthesis of Novel Coumarin Hybrids. ACS Comb. Sci. 2014, 16, 566–572. DOI: 10.1021/co500092b. (n) Kanchithalaivan, N.; Sivakumar, S.; Ranjith Kumar, R.; Elumalai, P.; Ahmed, Q. N.; Padala, A. K. Four-Component Domino Strategy for the Combinatorial Synthesis of Novel 1,4-Dihydropyrano[2,3-c]Pyrazol-6-Amines. ACS Comb. Sci. 2013, 15, 631–638. DOI: 10.1021/co4000997. (o) Sivakumar, S.; Kanchithalaivan, S.; Ranjith Kumar, R. A One-Pot Three-Component Domino Protocol for the Synthesis of Penta-Substituted 4H-Pyrans. RSC Adv. 2013, 3, 13357–13364. DOI: 10.1039/c3ra41510d. (p) Jeyachandran, V.; Ranjith Kumar, R.; Ali, M. A.; Choon, T. S. A One-Pot Domino Synthesis and Discovery of Highly Functionalized Dihydrobenzo[b]Thiophenes as AChE Inhibitors. Bioorg. Med. Chem. Lett. 2013, 23, 2101–2105. DOI: 10.1016/j.bmcl.2013.01.122. (q) Maharani, S.; Ranjith Kumar, R. On-Water’ One-Pot Pseudo Four-Component Domino Protocol for the Synthesis of Novel Benzo[a]Cyclooctenes. Tetrahedron Lett. 2013, 54, 4800–4802. DOI: 10.1016/j.tetlet.2013.06.139.
  • Sahoo, S. C.; Maity, R.; Pan, S. C. DBU-Mediated Addition of α-Nitroketones to α-Cyano-Enones and α,β-Unsaturated α-Ketoesters: Synthesis of Dihydrofurans and Conjugated Dienes. ACS Omega. 2019, 4, 2792–2803. DOI: 10.1021/acsomega.8b03651.
  • Crystallographic data for compounds 4b and 4l in this article have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers 1,023,393 and 1,023,391, respectively. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44 (0) 1223 336033 or e-mail:[email protected]).

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