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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 50, 2020 - Issue 6
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ARTICLES

Synthesis of some novel chloro-/aryl-substituted-5,5-dimethyl-2-cyclohexenones

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Pages 849-857 | Received 01 Oct 2019, Published online: 08 Feb 2020

References

  • (a) Horspool, W. M.; Armesto, D. In Organic Photochemistry – A Comprehensive Treatment; Horwood, E., Ed.; Bookcraft Ltd: Midsmer Norton, Great Britain, 1992. (b) Turro, N. J.; Ramamurthy, V.; Scaiano, J. C. In Modern Molecular Photochemistry of Organic Molecules; 1st Indian ed.; University Science Books: New Delhi. 2017. (c) Ohba, M.; Kawase, N.; Fujii, T. Total Syntheses of (±)-Agelasimine-A, (±)-Agelasimine-B, and (±)-Purino-Diterpene and the Structure of Diacetylagelasimine-A. J. Am. Chem. Soc. 1996, 118, 8250–8257. DOI: 10.1021/ja960879b. (d) Zhang, L.; Koreeda, M. Total Synthesis of (+)-Acanthodoral by the Use of a Pd-Catalyzed Metal-Ene Reaction and a Nonreductive 5- exo -Acyl Radical Cyclization. Org. Lett. 2004, 6, 537–540. DOI: 10.1021/ol0363063. (e) Jan, N. –W.; Liu, H.-J. An Enantioselective Total Synthesis of (+)-Ricciocarpin A. Org. Lett. 2006, 8, 151–540. DOI: 10.1021/ol052638r. (f) Gundersen, L.–L. Synthesis and Biological Activities of Marine Terpene-Adenine Hybrids and Synthetic Analogs. Phytochem. Rev. 2013, 12, 467–486. DOI: 10.1007/s11101-012-9236-6. (g) Felix, C. M. Marquette University, Milwaukee, WI. PhD. Dissertation, 2013.; (h) Almssy, A.; Paický, M.; Bohác, A.; Sališová, M.; Addová, G.; Rosenblum, M. Synthesis 2002, 12, 1695–1700. DOI: 10.1055/s-2002-33709.
  • Jyothi, D.; HariPrasad, S. Ind. J. Chem 2008, 47, 630–632.
  • (a) Venkatesha, M. A.; HariPrasad, S. Serb. J. Chem 2013, 78, 759–768.; (b) Jyothi, D.; HariPrasad, S. Cyclic α-Acylvinyl Anionic Synthons: A Novel Synthesis of 2-Trimethylsilyl-3-Methyl-Cyclohexenone by the Wurtz–Fittig Coupling Reaction. Syn. Comm 2009, 39, 875–879. DOI: 10.1080/00397910802432196.; (c) Jyothi, D.; HariPrasad, S. Arkivoc, 2012, vi, 194–203.
  • (a) Strand, T. M.; Ross, D. W.; Thistle, H. W.; Ragenovich, I. R.; Guerra, I. M.; Lamb, B. K. Predicting Dendroctonus Pseudotsugae (Coleoptera: Curculionidae) Antiaggregation Pheromone Concentrations Using an Instantaneous Puff Dispersion Model. J. Econ. Entom. 2012, 105, 451–460. DOI: 10.1603/EC11282.; (b) Ghostin, J.; Bordereau, C.; Braekman, J. C. Synthesis of Syn-4,6-Dimethyldodecanal, the Male Sex Pheromone and Trail-following Pheromone of Two Species of the Termite Zootermopsis. Nat. Prod. Res. 2011, 25, 560–568. DOI: 10.1080/14786419.2010.535152.
  • Jeevan Chakravarthy, A. S.; Krishnamurthy, M. S.; Begum, N. S.; HariPrasad, S. Synthesis of 1-Trimethylsilyl-2-Arylcyclohexenes: A New Class of Anionic Synthons. Tetrahedron Lett 2016, 57, 3231–3234. DOI: 10.1016/j.tetlet.2016.06.051.
  • Venkatesha, M. A.; HariPrasad, S. Palladium Catalyzed Synthesis of Some Novel (Spirocycloalkenyl) Trimethylsilylacetylenes. Loc. 2013, 10, 457–461. DOI: 10.2174/15701786113109990007.
  • Lokesh, K.; HariPrasad, S.; Roopashree, B.; Gayathri, V. Synthesis, Characterization and Catalytic Activity of a Novel 2-(3′- Aminophenyl) Benzimidazoyl Palladium (II) Complex. Ccat. 2015, 4, 125–132. DOI: 10.2174/2211544704666150508221808.
  • Jeevan Chakravarthy, A. S.; Krishnamurthy, M. S.; Begum, N. S.; HariPrasad, S. A Highly Efficient Synthesis of 1-Trimethylsilyl-2-Arylcyclopentenes Using Two Consecutive Stages of Aqueous and Anhydrous Reactions. Arkivoc, v 2018, 2018, 150–163. DOI: 10.24820/ark.5550190.p010.421.
  • Lokesh, K.; HariPrasad, S. Org. Chem. Int 2014, 2014, 6. DOI: 10.1155/2014/871595.
  • Weidmann, N.; Ketels, M.; Knochel, M. Natriierung Von Aromaten Und Heteroaromaten im Kontinuierlichen Durchfluss. Angew. Chem. 2018, 130, 10908–10911. DOI: 10.1002/anie.201803961.
  • Jeevan Chakravarthy, A. S.; Madhura, M. J.; Gayathri, V.; HariPrasad, S. Tetrahedron Letters, 2020, 61(2), in press. DOI: 10.1016/j.tetlet.2019.151391.
  • Jeevan Chakravarthy, A. S.; Krishnamurthy, M. S.; Begum, N. S.; HariPrasad, S. A Rapid Synthesis of 1-Chloro-2-Arylcyclohexenes Using MWAOS in Aqueous Media: single Crystal Studies of Two Representative Compounds. Mol. Cryst. Liq. Cryst 2019, 682, 65–76. DOI: 10.1080/15421406.2019.1655979.
  • O’Neil, M. J., Ed. The Merck Index an Encyclopedia of Chemicals. Drugs and Biologicals, 14th Ed.; Merck and Co., Inc.: N.J., USA, 2006; ONR – 104, 443.
  • Keaveney, S. T.; Kundu, G.; Schoenebeck, F. Modular Functionalization of Arenes in a Triply Selective Sequence: Rapid C(sp2) and C(sp3) Coupling of C−Br, C−OTf, and C−Cl Bonds Enabled by a Single Palladium(I) Dimer. Angew. Chem. 2018, 130, 12753–12757. DOI: 10.1002/ange.201808386.
  • (a) Faworsky, H. A.; Boshowsky, W. Zur Frage Nach Der Existenzfähigkeit Cyclischer Kohlenwasserstoffe Mit Einer Dreifachen Bindung im Ring. Justus Liebigs. Ann. Chem. 1912, 390, 122–129. DOI: 10.1002/jlac.19123900107.; (b) Still, I. W. J.; Kutney, G. W. Reactions of Dimedone with Sulfur Chlorides. J. Org. Chem. 1981, 46, 4911–4914. DOI: 10.1021/jo00337a017.; (c) Mishra, K.; Basavegowda, N.; Lee, Y. R. AuFeAg Hybrid Nanoparticles as an Efficient Recyclable Catalyst for the Synthesis of α,β- and β,β-Dichloroenones. Applied Catalysis A: General 2015, 506, 180–187. DOI: 10.1016/j.apcata.2015.09.014.
  • (a) Theeramunkong, S.; Caldarelli, A.; Massarotti, A.; Aprile, S.; Caprioglio, D.; Zaninetti, R.; Teruggi, A.; Pirali, T.; Grosa, G.; Tron, G. C.; Genazzani, A. A. Regioselective Suzuki Coupling of Dihaloheteroaromatic Compounds as a Rapid Strategy to Synthesize Potent Rigid Combretastatin Analogues. J. Med. Chem. 2011, 54, 4977–4986. DOI: 10.1021/jm200555r.; (b) Nubbermeyer, U. Product Subclass 1: 1,2-Dihaloalkenes. In Science of Synthesis; Georg ThiemeVerlag: Stuttgart 2008, 32, 57–168.
  • (a) Krebs, A.; Wilke, J. Top. Curr. Chem 1983, 69, 189–233. (b) Dommerholt, J.; Rutjes, F. P. J. T.; van Delft, F. L. Strain-Promoted 1,3-Dipolar Cycloaddition of Cycloalkynes and Organic Azides. Top Curr Chem 2016, 374, 16. DOI: 10.1007/s41061-016-0016-4.
  • (a) Komatsu, K.; Aonuma, S.; Jinbu, Y.; Tsuji, R.; Hirosawa, C.; Takeuchi, K. Generation and Oligomerization of Bicyclo[2.2.2]Octyne and Properties of Tris(Bicyclo[2.2.2]Octeno)Benzene Obtained from the Linear Trimer. J. Org. Chem. 1991, 56, 195–203. and references therein; DOI: 10.1021/jo00001a039.; (b) Voigt, K.; von Zezschwitz, P.; Rosauer, K.; Lansky, A.; Adams, A.; Reiser, O.; de Meijere, A. The Twofold Heck Reaction on 1,2-Dihalocycloalkenes and Subsequent 6π-Electrocyclization of the Resulting (E, Z, E)-1,3,5-Hexatrienes: A New Formal {2 + 2+2}-Assembly of Six-Membered Rings. Eur. J. Org. Chem. 1998, 1998, 1521–1534. DOI: 10.1002/(SICI)1099-0690(199808)1998:8<1521::AID-EJOC1521>3.0.CO;2-E.
  • (a) Wittig, G.; Pohlke, R. Zur Existenz Niedergliedriger Cycloalkine, II. Chem. Ber. 1961, 94, 3276–3286. DOI: 10.1002/cber.19610941214.; (b) Braun, J. V.; Ostermayer, H. Ber. Dtsch. Chem. Ges. A/B. 1937, 70, 1006–1008. DOI: 10.1002/cber.19370700525.; (c) Nagendrappa, G. Bromine Induced Autoxidation and Bromination Studies of Chlorinated Norbornenes. Tetrahedron 1989, 45, 6485–6498. DOI: 10.1016/S0040-4020(01)89525-9.; (d) Gassman, P. G.; Gennick, I. Synthesis and Reactions of 2-Lithio-3-Chlorobicyclo[2.2.1]Hept-2-Ene. Generation of the Trimer of Bicyclo[2.2.1]Hept-2-Yne. J. Am. Chem. Soc 1980, 102, 6863–6864. DOI: 10.1021/ja00542a040.; (e) Lennartson, A.; Quant, M.; Moth-Poulsen, K. Synlett 2015, 26, 1501–1504. DOI: 10.1055/s-0034-1380417.; (f) HariPrasad, S.; Nagendrappa, G. Reactions of 1,2-Dihalocycloalkenes with Alkali Metals in Presence of Chlorotrimethylsilane. Reductive Carbon-Carbon Bond Cleavage in Five Membered Homocyclic System. Tetrahedron 1993, 49, 3387–3396. DOI: 10.1016/S0040-4020(01)90165-6.; (g) Weber, J.; Brinker, U. H. Competing 1,n-Elimination Reactions of 1-Bromo-5-Bromomethyl-6,6-Dichlorobicyclo[3.1.0]Hexane: A Strained 1,3-Bridged Cyclopropene and a Vinylcarbene as Reactive Intermediates. Tetrahedron 1996, 52, 14641–14650. DOI: 10.1016/0040-4020(96)00912-X.; (h) Applequist, D. E.; Gebauer, P. A.; Gwynn, D. E.; O’Connor, L. H. Rearrangement of the Hindered Cyclobutadiene from Dimerization of 3,3,6,6-Tetramethylcyclohexyne. J. Am. Chem. Soc. 1972, 94, 4272–4278. DOI: 10.1021/ja00767a040.; (i) Marchand, A. P.; Aavula, B. R.; Bott, S. G. Syntheses and Reactions of Halogenated Pentacyclo[5.5.0.02,6.03,10.05,9]Dodec-11-Enes. Tetrahedron 1998, 54, 5105–5118. DOI: 10.1016/S0040-4020(98)00162-8.; (j) Peluso, P.; De Lucchi, O.; Cossu, S. Eur. J. Org. Chem. 2002, 23, 4032–4036. DOI: 10.1002/1099-0690(200212)2002:23<4032::AID-EJOC4032>3.0.CO;2-X.
  • (a) Kaplan, J. M.; Hruszkewycz, D. P.; Strambeanu, I. I.; Nunn, C. J.; VanGelder, K. F.; Dunn, A. L.; Wozniak, D. I.; Dobereiner, G. E.; Leitch, D. C. Scalable and Chemoselective Synthesis of γ-Keto Esters and Acids via Pd-Catalyzed Carbonylation of Cyclic β-Chloro Enones. Organometallics 2019, 38, 85–96. DOI: 10.1021/acs.organomet.8b00468.; (b) Yu, G.; Clive, D. L. J. Formation of Meta -Substituted Phenols by Transition Metal-Free Aromatization: Use of 2-Bromocyclohex-2-en-1-Ones. J. Org. Chem. 2016, 81, 8470–8484. DOI: 10.1021/acs.joc.6b01653.
  • Betts, B. E.; Davey, W. J. 651. Cyclohexane-1,3-Diones. Part VI. Structural Requirements for the Displacement of the Alkoxyl by the Cyano-Group in the Enol Ethers of Cyclic β-Diketones. J. Chem. Soc 1961, 0, 3333–3340. DOI: 10.1039/JR9610003333.
  • Magar, K. B. S.; Lee, Y. R. Adv. Synth. Catal. 2014, 356, 3422–3432. DOI: 10.1002/adsc.201400348.
  • (a) Castillo, R.; Reyes, M. J.; Izquierdo, M. L.; Builla, J. A. Suzuki Reaction on Pyridinium N-Haloheteroarylaminides: regioselective Synthesis of 3,5-Disubstituted 2-Aminopyrazines. Tetrahedron 2008, 64, 1351–1370. DOI: 10.1016/j.tet.2007.11.057.; (b) Laha, J. K.; Patel, K. V.; Saima, S.; Pandey, S.; Solanke, G.; Vashisht, V. Scope of Regioselective Suzuki Reactions in the Synthesis of Arylpyridines and Benzylpyridines and Subsequent Intramolecular Cyclizations to Azafluorenes and Azafluorenones. New J. Chem. 2018, 42, 16069–16074. DOI: 10.1039/C8NJ02734J.; (c) Handy, S. T.; Mayi, D. Regioselective Double Suzuki Couplings of 4,5-Dibromothiophene-2-Carboxaldehyde. Tetrahedron Letters 2007, 48, 8108–8110. DOI: 10.1016/j.tetlet.2007.09.114.
  • PhD. Dissertation 2015. Venkatesha, G. B. Bangalore University, Bangalore, INDIA.
  • The authors thank Dr. Nagarajaiah and Prof. Noor Shahina Begum (formerly at DOS in Chemistry, Central College Campus, Bangalore University: currently transferred to DOS in Chemistry, Jnana Bharathi Campus, Bangalore University, Bengaluru) for reducing the crystal data of the compound 3a.

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