2-N,N-Dialkylamino-1,3-Dithiolium Salts

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The synthesis of 2-N,N-dialkylamino-1,3-dithiolium salts is reviewed.

1. Schukat, G.; Fanghänel, E. 1,3-Dithiolium Salts, Se and Te Analogues, and Benzoannulated Analogues. Science of Synthesis 2002, 11, 191-229.

2. Meziere, C.; Allain, M.; Oliveras-Gonzalez, C.; Cauchy, T.; Vanthuyne, N.; Sarbu, L.G.; Birsa, L.M.; Pop, F.; Avarvari, N. Tetrathiafulvalene-[2.2]paracyclophanes: Synthesis, crystal structures, and chiroptical properties. Chirality 2018, 30, 568-575.

3. Babii, C.; Mihalache, G.; Bahrin, L.G.; Neagu, A.N.; Gostin, I.; Mihai, C.T.; Sarbu, L.G.; Birsa, L.M.; Stefan, M. A novel synthetic flavonoid with potent antibacterial properties: In vitro activity and proposed mode of action. Plos One 2018, 13, 1-15.

4. Bahrin, L.G.; Sarbu, L.G.; Jones, P.G.; Birsa, L.M.; Hopf, H. [2.2]Paracyclophane-Bis(triazole) Systems: Synthesis and Photochemical Behavior. Chem. Eur. J. 2017, 23 (50), 12338-12345.

5. Gorodea, I.A.; Sandu, I.; Sarbu, L.G. Novel 4-(3-Bromo-2-hydroxy-5-methylphenyl)-1,3-Dithiol-2-ylidene Derivatives. Rev. Chim. (Bucharest) 2017 68, 1988-1991.

6. Matei, M.; Sandu, I.; Birsa, M.L.; Sarbu, L.G.; Simion, L. New 4-(4-Hydroxyaryl)-5-Methyl-1,3-Dithiol-2-ylidene Derivatives. Rev. Chim. (Bucharest) 2017, 68, 81-84.

7. Pavel, S.; Hopf, H.; Jones, P.G.; Asaftei, I.V.; Sarbu, L.G.; Birsa, L.M. Click reactions with pseudo-geminal bis(azido-methylene)[2.2]paracyclophane. Monatsh. Chem. 2016, 147, 2179-2183.

8. Toader, E.; Bahrin, L.G.; Jones, P.G.; Hopf, H.; Sarbu, L.G.; Stoleriu, G. Synthesis of New Morpholine Containing Flavonoids with Potential Biological Applications. Rev. Chim. (Bucharest) 2016, 67, 1520-1522.

9. Dirtu, D.; Lungu, N.C.; Chirita, P.; Sandu, I.G.; Birsa, M.L.; Earar, K.; Sarbu, L.G. Synthesis of Novel 4-(3,5-Dibromo-2-hydroxyphenyl)-5-Methyl-1,3-Dithiol-2-ylidene Derivatives. Rev. Chim. (Bucharest) 2016, 67, 534-537.

10. Sarbu, L.G.; Bahrin, L.G.; Jones, P.G.; Birsa, M.L.; Hopf, H. [2.2]Paracyclophane derivatives containing tetrathiafulvalene moieties. Beilstein J. Org. Chem., 2015, 11, 1917-1921.

11. Sarbu, L.G.; Hopf, H.; Grunenberg, J.; Birsa, M.L. Reduction of Pseudo-geminal Bis(ethynyl)-Substituted [2.2]Paracyclophanes. Synlett, 2015, 26, 87-90.

12. Sarbu, L.G.; Hopf, H.; Jones, P.G.; Birsa, M.L. Selenium halide-induced bridge formation in [2.2]paracyclophanes. Beilstein J. Org. Chem., 2014, 10, 2550-2555.

13. Sarbu, L.G.; Bicu, E.; Hopf, H.; Birsa, M.L. [2.2]Paracyclophane Substituted Indolizines. Rev. Chim. (Bucharest), 2014, 65, 398-400.

14. Sarbu, L.G.; Birsa, A.; Hopf, H.; Birsa, M.L. New Bridges In [2.2]Paracyclophanes: The Interaction Of Chalcogenide Halides With Pseudo-Geminal Triple Bonds. Phosphorus, Sulfur, and Silicon, and the Related Elements 2011, 186, 1246-1250.

15. Sarbu, L.G.; Birsa, A.; Hopf, H.; Birsa, M.L. Heteroatom Bridged[2.2]Paracyclophanes As Enediyne Analogs. Acta Chem. Iasi 2010, 18, 186-193.

16. Sarbu, L.G.; Birsa, A.; Ignat, L.; Hopf, H.; Birsa, M.L. [2.2]Paracyclophanes: The Interaction of Pseudo-Geminal Bisacetylene with Water and Electrophiles. Acta Chem. Iasi, 2010, 18, 71-78.

17. Narita, M.; Pittman Jr, C.U. Preparation of Tetrathiafulvalenes (TTF) and their Selenium Analogs -Tetraselenafulvalenes (TSeF). Synthesis 1976, 489-514.

18. Schukat, G.; Richter, A.M.; Fanghänel, E. Synthesis, Reactions, and Selected Physico-Chemical Properties of 1,3-and 1,2-Tetrachalcogenafulvalenes. Sulfur Rep. 1987, 7, 155-127.

19. Schukat, G.; Fanghänel, E. Synthesis, Reactions, and Selected Physico-Chemical Properties of 1,3- and 1,2-Tetrachalcogenafulvalenes. Sulfur Rep. 1993, 14, 245-383.

20. Diaz, M.C.; Illescas, B.M.; Martin, N.; Perepichka, I.F.; Bryce, M.R.; Levillain, E.; Viruela, R.; Orti, E. Electronic interaction in new π-extended tetrathiafulvalenes dimers. Chem. Eur. J. 2006, 12, 2709-2721.

21. Ueno, Y.; Nakayama, A.; Okawara, M. An Improved Method for Methoxymethylation of Alcohols under Mild Acidic Conditions. Synthesis 1975, 276-277.

22. Hiratani, K.; Shiono, H.; Okawara, M. A New Synthetic Route To 1,3-Dithiolium Salts Involving Neighboring Group Participation Of Dithiocarbamate Group. Chem. Lett. 1973, 867-870.

23. Harris, R.L.N.; Oswald, L.T. The addition of dithiocarbamic acids to pbenzoquinone. Aust. J. Chem. 1974, 27, 1309-1316.

24. Nakai, T.; Hiratani, K.; Okawara, M. Tri(hetero)substituted Carbonium Ions. XI. A Novel Synthetic Route to 2-Dialkylamino-4-alkyl-1,3-dithiolium Salts. Bull. Chem. Soc. Jpn. 1976, 49, 827-828.

25. Leaver, D.; Robertson, W.A.H.; McKinnon, D.M. Synthesis of tetrathiafulvalenes. J. Chem. Soc. 1962, 5104-5109.

26. Campaigne, E.; Jacobsen, N.W. Dithiolium Derivatives. I. 2-Dialkylamino-1,3-dithiolium Perchlorates. J. Org. Chem. 1964, 29, 1703-1708.

27. Takamizawa, A.; Hirai, K. Studies on 1, 3-Dithiolium Cations. I. A Novel Synthetic Method of 4-p-Substituted Phenyl Derivatives and Related Compounds. Chem. Pharm. Bull. 1969, 17, 1924-1930.

28. Cascaval, A. Compusi mezoionici. Bul. Inst. Polit. Iasi 1987, XXXIII, fasc. 1-4, 47-50.

29. Cascaval, A. Compuşi organici mezoionici: Sidnone, Münchnone, Iaşinone, Ed. Univ. “Al.I. Cuza” Iaşi, 1995.

30. Birsa, M.L. Dithiolium derivatives. I. An. St. Univ.Al.I. CuzaIasi 1998, VI, 57-64.

31. Birsa, M.L. Dithiolium derivatives. II. An. St. Univ.Al.I. CuzaIasi 1999, VII, 341-347.

32. Dirtu, D.; Asaftei, I.V.; Chirita, P.; Sandu, I.G.; Birsa, M.L.; Earar, K.; Sarbu, L.G. Synthesis of 1,3-Dithiol-2-ylium Salts by Functionalization of Some Toluenols. Rev. Chim. (Bucharest) 2015, 66, 2028-2030.

33. Chirita, P.; Asaftei, I.V.; Sandu, I.; Sarbu, L.G.; Lupu, V.V. Mesoionic 4-(2-Dialkylamino-1,3-dithiol-2-ylium-4-yl)phenolates. Rev. Chim. (Bucharest) 2017 68, 147-150.

34. Chirita, P.; Duinea, M.I.; Sandu, A.M.; Birsa, L.M.; Sarbu, L.G.; Baibarac, M.; Sava, F.; Popescu, M.; Matei, E. Inhibitory effect of three phenacyl derivatives on the oxidation of sphalerite (ZnS) in air-equilibrated acidic solution. Corros. Sci. 2018, 138, 154-162.

35. Asaftei, I.V.; Sandu, I.G.; Lungu, N.C.; Birsa, M.L.; Sarbu, L.G.; Ignat, M. Conversion of Butane-Butylene Mixtures over B(Al)-HZSM-5 Catalyst Prepared by Impregnation and over ZnO/HZSM-5 co-Catalyst Prepared by Mechanical Mixing. Rev. Chim. (Bucharest) 2016, 67(5), 847-853.

36. Birsa, M.L. Synthesis of some 4-(2’-hydroxyaryl)-5-ethyl-2-(N, N-dialkylamino)-1,3-dithiolium salts. Sulfur Lett. 2003, 26, 155-162.

37. Asaftei, I.V.; Lungu, N.C.; Birsa, M.L.; Sarbu, L.G.; Ignat, M.; Sandu, I.G. Conversion of Light Hydrocarbons From Petroleum Refining Processes Over Zn-HZSM-5 (Nitrate) and Zn-HZSM-5 (Acetate) Catalyst A comparative study. Rev. Chim. (Bucharest) 2016, 67(8), 1523-1528.

38. Goanta, M.; Ciobanu, A.S.; Birsa, A.; Asaftei, I.V.; Birsa, M.L. Synthesis of 4-(3-Bromo-2-Hydroxy-5-Methylphenyl)-2-Dialkylamino-1,3-Dithiolium Chlorides. Acta Chem. Iasi 2009, 17, 35-48.

39. Sarbu, L.G.; Bahrin, L.G. 3-Methylpiperidinyl Carbodithioates as Building Blocks for 1,3-Dithiolium Derivatives. Acta Chem. Iasi 2013, 21, 47-56.

40. Sarbu, L.G.; Birsa, M.L. Synthesis of Iodine Containing Mesoionic 2-(1,3-Dithiolium)phenolates. Acta Chem. Iasi 2011, 19, 125-135.

41. Bahrin, L.G.; Jones, P.G.; Hopf, H. Tricyclic flavonoids with 1,3-dithiolium substructure. Beilstein J. Org. Chem. 2012, 8, 1999-2003.

42. Sarbu, L.G.; Hrib, C.G.; Birsa, M.L. rac-1-(5-Bromo-2-hydroxyphenyl)-1-oxopropan-2-yl morpholine-4-carbodithioate. Acta Cryst. 2013, E69, o1169.

43. Lungu, N.C., Sandu, I., Chirita, P., Birsa, M.L. New water soluble 1,3-dithiolium salt. Rev. Chim. (Bucharest) 2013, 64, 697-700.

44. Buhaceanu, R.; Lungu, N.C.; Forna, N.C.; Asaftei, I.V.; Chirita, P.; Birsa, M. L. A new class of mesoionic 4-(1,3-dithiol-2-ylium)phenolates. Rev. Chim. (Bucharest) 2013, 64, 803-807.

45. Buhaceanu, R.; Lungu, N.C.; Forna, N.C.; Asaftei, I.V.; Chirita, P.; Birsa, M.L. The influence of bromine substituent on optical properties of some 1,3-dithiolium derivatives. Rev. Chim. (Bucharest) 2013, 64, 960-964.

46. Bahrin, L.G.; Lungu, N.C.; Forna, N.C.; Sandu, I.; Birsa, M.L. Zwitterionic 3-(1,3-dithiol-2-ylium)phenolates. Rev. Chim. (Bucharest) 2013, 64, 1343-1346.

47. Sarbu, L.G.; Lungu, N.C.; Forna, N.C.; Birsa, M.L. Synthesis of 4-(2-hydroxyphenyl)-2-dialkylamino-1,3-dithiolium salts and corresponding mesoionic derivatives. Rev. Chim. (Bucharest) 2013, 64, 1404-1407.

48. Asaftei, I.V.; Lungu, N.C.; Birsa, L.M.; Sandu, I.G.; Sarbu, L.G.; Ignat, M. Performance of Ag-HZSM-5 Zeolite Catalysts in n-heptane Conversion. Rev. Chim. (Bucharest), 2017 68, 116-120.

49. Lungu, N.C.; Bahrin, L.G.; Asaftei, I.V.; Forna, N.C.; Sandu, I.; Birsa, M.L. Phenacyl 3-methylpiperidinyl carbodithioates as building blocks for 1,3-dithiolium derivatives. Rev. Chim. (Bucharest) 2014, 65, 181-184.

50. Sarbu, L.G.; Lungu, N.C.; Asaftei, I.V.; Sandu, I.; Birsa, M.L. New evidence for the mesoionic character of 2-(1,3-Dithiol-2-ylium)phenolates. Rev. Chim. (Bucharest) 2014, 65, 325-327.

51. Sarbu, L.G.; Bicu, E.; Belei, D. Synthesis of Mesoionic [2-(10H-phenothiazinyl)-1,3-dithiolium]phenolates. Rev. Chim. (Bucharest) 2014, 65, 249-252.

52. Bahrin, L.G.; Asaftei, I.V.; Sandu, I.G.; Sarbu, L.G. Synthesis of (4-Methylpiperazin-1-yl)carbodithioates and of their 1,3-Dithiolium Derivatives. Rev. Chim. (Bucharest) 2014, 65, 1046-1049.

53. Sarbu, L.G.; Lungu, N.C.; Balan, A.; Bahrin, L.G. Synthesis of Sulfur Containing Piperazine Derivatives with Potential Biological Activities. Rev. Chim. (Bucharest) 2014, 65, 1135-1138.

54. Sarbu, L.G.; Apostu, M.O.; Sandu, I.G.; Manea, L.R.; Bahrin, L.G. 1,3-Dithiol-2-ylium Compounds Derived from Substituted Butyrophenone Rev. Chim. (Bucharest) 2014, 65, 1327-1330.

55. Bahrin, L.G.; Apostu, M.O.; Birsa, M.L.; Stefan, M. The antibacterial properties of sulfur containing flavonoids. Bioorg. Med. Chem. Lett. 2014, 24, 2315-2318.

56. Birsa, M.L.; Sandu, A.V.; Balan, A. Synthesis of new 1,3-dithiolium derivatives from 4-hydroxyacetophenones. Rev. Chim. (Bucharest) 2014, 65, 1435-1438.

57. Hrib, C.G.; Sandu, I.; Earar, K.; Birsa, M.L. Synthesis of new 1,3-dithiolium derivatives from propiophenones. Rev. Chim. (Bucharest) 2014, 65, 1453-1456.

58. Apostu, M.O.; Sandu, I.; Birsa, M.L.; Earar, K. Synthesis of novel 4-aryl-5-methyl-1,3-dithiolium derivatives. Rev. Chim. (Bucharest) 2015, 66, 39-42.

59. Sarbu, L.G.; Sandu, I.; Bahrin, L.G.; Balan, A.; Apostu, M.O. New Bromo Substituted 1,3-Dithiol-2-ylium Salts. Rev. Chim. (Bucharest) 2015, 66, 55-58.

60. Chirita, P.; Hrib, C.G.; Lungu, N.C.; Sarbu, L.G.; Earar, K. A New Class of 4-(Hydroxyaryl)-1,3-Dithiolium Chlorides. Rev. Chim. (Bucharest) 2015, 66, 1151-1153.

61. Hrib, C.G.; Chirita, P.; Sandu, I.G.; Asaftei, I.V.; Sarbu, L.G.; Earar, K. The Synthesis and X-Ray Structural Characterization of New 4-(5-Bromo-2-hydroxyphenyl)-1,3-Dithiol-2-ylium Perchlorates. Rev. Chim. (Bucharest) 2015, 66, 983-985.

62. Bahrin, L.G.; Jones, P.G.; Hopf, H.; Earar, K.; Birsa, M.L. Synthesis of new iodine containing 1,3-dithiol-2-ylium salts. Rev. Chim. (Bucharest) 2016, 67, 61-63.

63. Bahrin, L.G.; Jones, P.G.; Hopf, H.; Poroch, V.; Birsa, M.L. Synthesis of fluorine containing 1,3-dithiol-2-ylium salts. Rev. Chim. (Bucharest) 2016, 67, 481-484.

64. Bahrin, L.G.; Hopf, H.; Jones, P.G.; Sarbu, L.G.; Babii, C.; Mihai, A.C.; Stefan, M.; Birsa, M.L. Antibacterial structure–activity relationship studies of several tricyclic sulfur-containing flavonoids. Beilstein J. Org. Chem. 2016, 12, 1065-1071.

65. Bahrin, L.G.; Sarbu, L.G.; Hopf, H.; Jones, P.G.; Babii, C.; Stefan, M.; Birsa, M.L. The influence of halogen substituents on the biological properties of sulfur-containing flavonoids. Bioorg. Med. Chem. 2016, 24, 3166-3173.

66. Birsa, M.L.; Ganju, D. Synthesis and UV/Vis spectroscopic properties of new [2-(N,N-dialkylamino)-1,3-dithiolium-4-yl]phenolates. J. Phys. Org. Chem. 2003, 16, 207-212.

67. Eaton, P.E.; Carlson, G.R.; Lee, J.T. Phosphorus pentoxide-methanesulfonic acid. Convenient alternative to polyphosphoric. J. Org. Chem. 1973, 38, 4071-4073.

68. Birsa, M.L. A new approach to preparation of 1,3-dithiolium salts. Synth. Commun. 2001, 31, 1271-1275.

69. Birsa, M.L.; Asaftei, I.V. Solvatochromism of mesoionic iodo(1,3-dithiol-2-ylium-4-yl)phenolates. Monat. Chem. 2008, 139, 1433-1438.

70. Andersen, J.R.; Patel, V.V.; Engler, E.M. Bis-1,3-dithiole chemistry: Synthesis of compounds containing the 4,4′bis-(1,3-dithiole) unit. Tetrahedron Lett. 1978, 239-242.

71. Ueno, Y.; Masuyama, Y.; Okawara, M. Synthesis and Complex Formation of Macromolecules Having Tetrathiofulvalene Structure. Chem. Lett. 1973, 603-606.

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