104
Views
7
CrossRef citations to date
0
Altmetric
Original Articles

Efficient synthesis of novel bis(arylmethylidenes) of the 2,2-dimethyl-1,3-dithian-5-one system

, , , &
Pages 259-268 | Received 04 Oct 2015, Accepted 06 Dec 2015, Published online: 05 Jan 2016

References

  • Rideout DC, Breslow R. Hydrophobic acceleration of Diels–Alder reactions. J Am Chem Soc. 1980;102:7816–7817. doi: 10.1021/ja00546a048
  • Breslow R, Maitra U. On the origin of product selectivity in aqueous Diels-Alder reactions. Tetrahedron Lett. 1984;25:1239–1240. doi: 10.1016/S0040-4039(01)80122-2
  • Grieco PA, Garner P, He Z-M. “Micellar” catalysis in the aqueous intermolecular Diels-Alder reaction: rate acceleration and enhanced selectivity. Tetrahedron Lett. 1983;24:1897–1900. doi: 10.1016/S0040-4039(00)81800-6
  • Grieco PA, Yoshida K, Garner P. Aqueous intermolecular Diels-Alder chemistry: reactions of diene carboxylates with dienophiles in water at ambient temperature. J Org Chem. 1983;48:3137–3139. doi: 10.1021/jo00166a051
  • Dicks AP. A review of aqueous organic reactions for the undergraduate teaching laboratory. Green Chem Lett Rev. 2009;2:9–21 doi: 10.1080/17518250902820182
  • Li C-J, Chan T-H. Comprehensive organic reactions in aqueous media. 2nd ed. Hoboken: John Wiley & Sons; 2007.
  • Engberts JBFN. Organic chemistry in water: green and fast. In: Tundo P, Perosa A, Zecchini F, editors. Methods and reagents for green chemistry: an introduction. Hoboken: John Wiley & Sons; 2007. p. 159–170.
  • Mojtahedi MM, Khalili S. Rapid, benign, and additive-free thiolysis of epoxides under ultrasonic/aqueous conditions. J Sulfur Chem. 2014;35:431–437. doi: 10.1080/17415993.2014.909814
  • Simon M-O, Li C-J. Green chemistry oriented organic synthesis in water. Chem Soc Rev. 2012;41:1415–1427. doi: 10.1039/C1CS15222J
  • Li C-J. Organic reactions in aqueous media with a focus on carbon-carbon bond formations: a decade update. Chem Rev. 2005;105:3095–3166. doi: 10.1021/cr030009u
  • Datta M, Hunter AD, Zeller M. Synthesis, crystal structures and non-bonded S⋅⋅⋅S contacts with O─H⋅⋅⋅O/O─H⋅⋅⋅S hydrogen bonds in isomeric hydroxyphenyl-1,3-dithianes. J Sulfur Chem. 2013;34:502–511. doi: 10.1080/17415993.2012.762919
  • Hamrouni K, Saied T, Abed NE, Ahmed SBH, Boujlel K, Khoud MLB. Electrogenerated base-promoted synthesis and antimicrobial activity of 2-(1,3-dithian-2-ylidene)-2-arylacetonitrile and 2-(1,3-dithiolan-2-ylidene)-2-arylacetonitrile. J Sulfur Chem. 2015;36:196–206. doi: 10.1080/17415993.2015.1005620
  • Ando W, Kumamoto Y, Takata T. Reactions of cyclic disulfides with carbenes; desulfurization and insertion. Tetrahedron Lett. 1985;26:5187–5190. doi: 10.1016/S0040-4039(00)98899-3
  • Bennett GM, Scorah LVD. Studies in the penthian series. Part I. The action of sodium ethoxide on ethyl β-thiodipropionate. J Chem Soc. 1927;194–200. doi: 10.1039/jr9270000194
  • Bertini V, Lucchesini F, Pocci M, Alfei S. Soluble and insoluble polymeric 1,3-dithiane reagents for the synthesis of aldehydes from alkyl halides. Tetrahedron. 2005;61:9519–9526. doi: 10.1016/j.tet.2005.07.091
  • Romagnoli R, Baraldi PG, Pavani MG, et al. Synthesis and biological evaluation of allosteric A1-Adenosine receptor modulators structurally related to (2-amino-4,5,6,7-tetrahydro-benzo[b]thiophene-3-yl)-(4-chloro-phenyl)-methanone, a potent compound useful to reduce neuropathic pain. Med Chem Res. 2005;14:125–142. doi: 10.1007/s00044-005-0129-8
  • Romagnoli R, Pavani MG, Nuñez MC, et al. Synthesis and biological effects of novel 2-amino-3-naphthoylthiophenes as allosteric enhancers of the A1 adenosine receptor. J Med Chem. 2003;46:794–809. doi: 10.1021/jm0210212
  • Cox MT, Godfrey AA, Ridsdale CMJ. Spirocyclic β-oxo sulphoxides and sulphones as potential aldose reductase inhibitors. Chem Soc Perkin Trans 1. 1988:3217–3221. doi: 10.1039/p19880003217
  • Curtis NJ, Brown RS. Nitrogen- and sulfur-containing models for metallo-enzymes. Part I. synthesis and physical studies of 2(2-pyridy1)-1,3-dithioalkyl-2-propanols,2 (2-pyridy1)- and 2(2-imidazoly1)- l,3-dimercapto-2-propanols. Can J Chem. 1981;59:65–10. doi: 10.1139/v81-012
  • Stachel H-D, Zoukas T, HuDlein M, Nienaber J, Schorp M. Synthese von 1,2-dithiolo-furanen. Liebigs Ann Chem. 1993:305–311. doi: 10.1002/jlac.199319930151
  • Artico M, Di Santo R, Costi R, et al. Geometrically and conformationally restrained cinnamoyl compounds as inhibitors of HIV-1 integrase: synthesis, biological evaluation, and molecular modeling. J Med Chem. 1998;41:3948–3960. doi: 10.1021/jm9707232
  • Selvendiran K, Ahmed S, Dayton A, et al. Safe and targeted anticancer efficacy of a novel class of antioxidant-conjugated difluorodiarylidenyl piperidones: differential cytotoxicity in healthy and cancer cells. Free Radical Bio Med. 2010;48:1228–1235. doi: 10.1016/j.freeradbiomed.2010.02.009
  • Hathaway BA. An aldol condensation experiment using a number of aldehydes and ketones. J Chem Edu. 1987;64:367–368. doi: 10.1021/ed064p367
  • Mojtahedi MM, Abaee MS, Samianifard M, et al. Ultrasound mediation for efficient synthesis of monoarylidene derivatives of homo- and heterocyclic ketones. Ultrason Sonochem. 2013;20:924–930. doi: 10.1016/j.ultsonch.2012.11.004
  • Abaee MS, Mojtahedi MM, Zahedi MM, Sharifi R, Khavasi H. Efficient synthesis of novel 3-substituted-thiopyran-4-ones. Synthesis. 2007;39:3339–3344.
  • Abaee MS, Mojtahedi MM, Pasha GF, et al. Switching the reactivity of dihydrothiopyran-4-one with aldehydes by aqueous organocatalysis: Baylis-Hillman, aldol, or aldol condensation reactions. Org Lett. 2011;13:5282–5285. doi: 10.1021/ol202145w
  • Abaee MS, Cheraghi S. Efficient three-component Gewald reactions under Et3N/H2O conditions. J Sulfur Chem. 2014;35:261–269. doi: 10.1080/17415993.2013.860141
  • Abaee MS, Mojtahedi MM, Zahedi MM, Sharifi R, Mesbah AW, Massa W. Synthesis and structural elucidation of novel bisarylmethylidenes of cyclic enones. Synthetic Commun. 2007;37:2949–2957. doi: 10.1080/07370650701471756
  • Abaee MS, Mojtahedi MM, Zahedi MM. An efficient and improved method for the synthesis of bis(arylmethylidene)thiopyranones. Synlett. 2005;16:2317–2320. doi: 10.1055/s-2005-872656
  • Abaee MS, Mojtahedi MM, Zahedi MM, Sharifi R. A highly efficient method for solvent-free synthesis of bisarylmethylidenes of pyranones and thiopyranones. Heteroatom Chem. 2007;18:44–49. doi: 10.1002/hc.20252
  • Abaee MS, Mojtahedi MM, Hamidi V, Mesbah AW, Massa W. The first synthesis of bis(arylmethylidene)dioxan-5-ones: potential scaffolds to access vicinal tricarbonyl derivatives. Synthesis. 2008;40:2122–2126. doi: 10.1055/s-2008-1067114
  • Abaee MS, Mojtahedi MM, Sharifi R, Mesbah AW, Massa W. Lithium bromide mediated synthesis and X-Ray analysis of bisarylmethylidenes of piperidinone system. Chem Listy. 2008;102:s956–s958.
  • Hall HK Jr. Potentiometric determination of the base strength of amines in non-protolytic solvents. J Phys Chem. 1956;60: 63–70. doi: 10.1021/j150535a017
  • Cravotto G, Borretto E, Oliverio M, Procopio A, Penoni A. Organic reactions in water or biphasic aqueous systems under sonochemical conditions. A review on catalytic effects. Catal Commun. 2015;63:2–9. doi: 10.1016/j.catcom.2014.12.014
  • Lüttringhaus A, Prinzbach H. Cyclische disulfide, II: Normale, mittlere und makrocyclische β.β′-dithia-cyclanone durch Dieckmann-kondensation. Justus Liebigs Ann Chem. 1959; 624:79–97. doi: 10.1002/jlac.19596240108
  • APEX2, SADABS and SAINT. Madison, Wisconsin, USA: Bruker AXS Inc.; 2010.
  • Brandenburg K. Diamond, crystal and molecular structure visualization, crystal impact, Dr. H. Putz & Dr. K. Brandenburg GbR, Bonn, Germany, 2014.
  • Sheldrick GM. A short history of SHELX. Acta Cryst. 2008;64:112–122. doi: 10.1107/S0108767307043930

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.