Diaminothiadiazoles – Building Blocks for Macroheterocycles | Журнал "Макрогетероциклы"

Elena A. Danilova, Tat’yana V. Melenchuk, Olga N. Trukhina, and Mikhail K. Islyaikin^@

Ivanovo State University of Chemistry and Technology, 7, Engels Av., 153000, Ivanovo, Russia

^@Corresponding author E-mail: islyaikin@isuct.ru

DOI: 10.6060/mhc2010.1.68

Macroheterocycles 2010 3(1) 68-81

Syntheses and properties of 2,5-diamino-1,3,4-thiadiazole, 3,5-diamino-1,2,4-thiadiazole and 3-N-alkyl-5-amino-2-imino-1,3,4-thiadiazolines – building blocks for macroheterocyclic compounds are discussed in this review. The convenient methods of their synthesis were elaborated and peculiarities of their geometrical structure were discussed. The mechanism of 3,5-diamino-1,2,4-thiadiazole formation from 2-imino-4-thiobiuret was simulated by quantum chemistry methods at the level of Density Functional Theory (DFT).

References:

Click here to expand or collapse this section

1. Semigolovskiy N.Y. Anesteziologiya I Reanimatologiya 1998, 2, 56-59 (in Russ).

2. Smirnov A.V., Krivoruchko B.I. Anesteziologiya I Reanimatologiya 1998, 2, 51-55 (in Russ).

3. Smirnov A.V., Krivoruchko B.I. Anesteziologiya I Reanimatologiya 1997, 3, 97-98 (in Russ).

4. Krapivin S.V, Malishev A.Y., Kharitonov A.V., Ermishina O.S., Shubin S.N., Luk'yanova L.D. Vestnik RAMN 2002, 8, 32-37 (in Russ).

5. Werber G., Buccheri, Gentile M. J. Heterocyclic Chem. 1977, 14, 1263-1265.
http://dx.doi.org/10.1002/jhet.5570140727

6. Danilova E.A, Islyaikin M.K. Izv. Vyssh. Uchebn. Zaved.,Khim. Khim. Tekhnol. 1994, 37, 77-81 (in Russ).

7. Islyaikin M.K., Danilova E.A., Yagodarova L.D., Rodríguez- Morgade M.S., Torres T. Org. Lett. 2001, 3, 2153 – 2156.
http://dx.doi.org/10.1021/ol015924l

8. Islyaikin M.K., Danilova E.A., Kudrik E.V. In: Uspekhi Khimii Porfirinov (Advances in Porphyrin Chemistry) (Golubchikov O.A., Ed.) Snt.-Petersburg: NII KhimiiSpbGU 1999, Vol. 2, 300-319 (in Russ).

9. Islyaikin M.K., Borodkin V.F., Danilova E.A., Konovalov S.P., Panov A.A. Izv. Vyssh. Uchebn. Zaved.,Khim. Khim. Tekhnol. 1990, 33, 18-21 (in Russ).

10. Danilova E.A., Melenchuk T.V., Islyaikin M.K. In: Allrussian Conference "PrirodnieMakrogeterotsiklicheskieSoedineniyaiikhSinteticheskieAnalogi" ("Natural Macroheterocyclic Compounds and their Synthetical Analogs") April 2–5, 2007. Russia, Siktivkar, 2007, p. 52 (in Russ).

11. Melenchuk T.V., Danilova E.A., Islyaikin M.K. In: Allrussian Conference "PrirodnieMakrogeterotsiklicheskieSoedineniyaiikhSinteticheskieAnalogi" ("Natural Macroheterocyclic Compounds and their Synthetical Analogs"), April 2–5, 2007. Russia, Siktivkar, 2007, p. 83 (in Russ).

12. Melenchuk T.V., Danilova E.A., Islyaikin M.K. In: 29th Scientific Session on the Chemistry of Porphyrins and their Analogs, December 26, 2006. Russia, Ivanovo: ISUCT. 2006, p.76 (in Russ).

14. Joule J.A., Mills K. Heterocyclic Chemistry. Blackwell Science, 2004. 728 p.

15. Mashkovskii M.D. LekarstvennieSredstva (Medicinal Remedies), Moscow: Izdatelstvo Novaya Volna, 2002. 540 p. (in Russ).

16. The Chemistry of Synthetic Dyes (Venkataraman K., Ed.) New York: Academic Press, 1971. 541 p.

18. Ivanskii V.I. KhimiyaGeterotsiklicheskikhSoedinenii (Chemistry of Heterocyclic Compounds) Moscow: Vishaya Shkola, 1978. 559 p. (in Russ).

19. Heterocyclic Compounds (Elderfild R., Ed.) New York, 1961, Vol. 7. 467 p.

20. Barton D., Ollis Y. D. Comprehensive Organic Chemistry, Vol. 9: Sulfur Compounds, 1985, 800 p.

22. Fromm E. Ann. der Chemie 1922, 426, 313-345 (in Germ).
http://dx.doi.org/10.1002/jlac.19224260310

23. Fromm E. Ann. der Chemie 1923, 433, 1-9 (in Germ).
http://dx.doi.org/10.1002/jlac.19234330102

24. Busch H., Lotz. L. J. Prak. Chem. 1914, 90, 257-273.
http://dx.doi.org/10.1002/prac.19140900112

25. Senda H., Maruha J. Acta Cryst. 1987, 43, 347-349.
http://dx.doi.org/10.1107/S010827018709588X

26. Antolini L., Cornia A., Fabretti A.C., Malavasi J. Crystall. and Spectroscopic Research 1993, 23, 967-971.
http://dx.doi.org/10.1007/BF01185545

27. Gel’mbol’dt V.O., Ilyukhin A.B., Ganin E.V., Ennan A.A. Rus. J. Coord. Chem. 2001, 27, 573 –577.
http://dx.doi.org/10.1023/A:1009591603085

28. Senda H., Matsuoka H., Maruha J. Acta Cryst. 1986, C42, 1087-1089.
http://dx.doi.org/10.1107/S0108270186093368

30. Melenchuk T.V., Danilova E.A., Stryapan M.G., Islyaikin M.K., Russ. J. Gen. Chem. 2008, 78, 495 - 499.
http://dx.doi.org/10.1134/S1070363208030237

31. Stolle R., Fehrebach K. J. Prak. Chemie 1929, 122, 289-318 (in Germ).
http://dx.doi.org/10.1002/prac.19291220111

32. Guha P.C. J. Am. Chem. Soc. 1923, 45, 1036 – 1042.
http://dx.doi.org/10.1021/ja01657a024

33. Guha P.C., Mehta D.R. Chem. Abstr. 1939, 33, 598-599.

34. Fromm E., Layer H., Nerr N. Ann. der Chemie 1923, 433, 1-8 (in Germ).
http://dx.doi.org/10.1002/jlac.19234330102

35. Busch M., Holzmann Her. Ber. 1901, 34, 320-345.
http://dx.doi.org/10.1002/cber.19010340152

36. Busch M., Schmidt R. J. Prak. Chem. 1931, 130, 342-346 (in Germ).
http://dx.doi.org/10.1002/prac.19311300126

37. Bambas L.L. In: Five-membered Heterocyclic Compounds with Nitrogen and Sulfur or Nitrogen, Sulfur and Oxygen. New York, London: Interscience publishers LTD, 1952, p. 124-142.

38. Werber G., Buccheri, Gentile M. J. Heterocyclic Chem. 1977, 14, 1263–1265.
http://dx.doi.org/10.1002/jhet.5570140727

39. Islyaikin M.K. Synthesis, Structure Peculiarities and Properties of Substituted Macrohetrocyclic Compounds and their Metallocomplexes). Dis. Dr. Chem. Sci. Ivanovo State University of Chemistry and Technology, 2004. 353 p. (in Russ).

40. Danilova E.A., Melenchuk T.V., Islyaikin M.K. In: 23nd International Symposium on Organic Chemistry of Sulfur. June 29 – July 4, 2008. Russia, Moscow. 2008, p. 81-82.

41. Melekhonova E.E., Melenchuk T.V. In: Scientific Conference of the Festival of Students, Post-graduate Students and Young Scientists. April 20-24, 2009. Russia, Ivanovo: Ivanovo State University, Part VIII, 2009, p.53.

42. Tomchin A.B., Etingova N.I., Smirnov A.V., Vainshtein V.A., Munzhukova M.Y., Marysheva V.V., Krivoruchko B. I., Shustov E.B. Pat. 2096043 RF, 1997.

43. Kurzer F. J. Chem. Soc. 1955, 1-6.
http://dx.doi.org/10.1039/jr9550000001

44. Stratton K., Davis E.M. Int. J. Radiat. Biol. 1962, 5, 105-121.
http://dx.doi.org/10.1080/09553006214550621

45. Zarubina I.V., Mironova O.P., Krivoruchko B.I., Smirnov A.V. Voprosy Biologicheskoi, Medicinskoi i Farmacevticheskoi Khimii: Kvartal’nyi Nauchno-Practicheskii Zhurnal 2001, 1, 51-55 (in Russ).

46. Marysheva V.V. Obzory po Klinicheskoi Farmakologii i Lekarstvennoi Terapii: Recenziruemyi Nauchno- Praktichteskii Zhurnal 2007, 5, 17-27 (in Russ).

47. Bulanov Y.B. Anabolicheskie Sredstva (Anabolic Remedies). 2004. http://bulanoff.ru/anabolic.html.

48. Castro A., Castano T., Encinas A., Porcal W., Gil C. Bioorg. Med. Chem. 2006, 14, 1644 – 1652.
http://dx.doi.org/10.1016/j.bmc.2005.10.012

49. Baumann E. Ber., 1873, 6, 1371-1377.
http://dx.doi.org/10.1002/cber.187300602149

50. Sheehan J.C., Buchi G., Knutson D. Organic Syntheses 1963, 4, 502-504.

51. Zasosov V.A., Metelkova E.I., Voljina O.N., Shagalov L.B., Vlasov A.S. Med. Promishlennost 1963, 9, 15-22 (in Russ).

52. Melenchuk T.V., Konovalova E.A., Danilova E.A., Islyaikin M.K. Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol. 2008, 51, 125-127 (in Russ).

54. Kon V. Uspekhi Fiz. Nauk 2002, 172, 336-348 (in Russ).
http://dx.doi.org/10.3367/UFNr.0172.200203e.0336

55. Granovsky A.A. PC GAMESS version 7.1.E (FireFly), build number 5190
http://classic.chem.msu.su/gran/gamess/index.html

56. Zhurko G.A. Chemcraft. http://www.chemcraftprog.com/.

57. Minkin V.I., Simkin B.Ya., Minyaev R.M. Kvantovaya Khimiya Organicheskikh Soedinenii. Mehanizmi Reakcii (Quantum Chemistry of Organic Compounds. Reaction Mechanisms) Moscow: Khimiya, 1986. 248 p. (in Russ).

58. Gillespi Er. Model Ottalkivaniya Elektronnikh Par Valentnoi Obolochki i Stroenie Molekul (The Model of Repulsion of Electron Pairs of the Valent Shell) Moscow: Mir, 1992. 296 p. (in Russ).

59. Lybimtsev A.V., Baran’ski A., Islyaikin M.K., Smirnov R.P. Chem. Heterocycl. Comp. 1997, 8, 1074-1079.

60. Chikwana E., Simoyi R.H. J. Phys. Chem. 2004, 108, 1024-1032.
http://dx.doi.org/10.1021/jp0367068

61. Chikwana E., Otoikhian A., Simoyi R.H. J. Phys. Chem., A 2004, 108(52), 11591 – 11599.
http://dx.doi.org/10.1021/jp045897r

62. Makarov S.V., Mundoma C., Penn J.H., Svarovski S.A., Simoyi R.H. J. Phys. Chem. 1998, 102, 6786-6792.
http://dx.doi.org/10.1021/jp981713v

63. Hołyńska M., Kubiak M. Acta Crystal. 2008, C64, o609–o612.
http://dx.doi.org/10.1107/S0108270108032769

Attachment	Size
MHC2010_t03n01_68-81.pdf	990.05 KB

Журнал "Макрогетероциклы"

Navigation

Languages

News

Search

Diaminothiadiazoles – Building Blocks for Macroheterocycles

References: