Preferencje help
Widoczny [Schowaj] Abstrakt
Liczba wyników
2004 | 2 | 1 | 220-233
Tytuł artykułu

Aromatic glyoxalimines in criss-cross cycloaddition reactions

Treść / Zawartość
Warianty tytułu
Języki publikacji
Aromatic 1,4-diazabuta-1,3-dienes in glacial acetic acid with thiocyanates produce via criss-cross cycloaddition reactions the corresponding perhydroimidazo[4,5-d]imidazole-2,5-dithiones. When a mixture of thiocyanate and cyanate in a proper ratio was reacted together, nonsymmetrical 5-thioxo-perhydroimidazo[4,5-d]imidazole-2-ones were isolated. With cyanates substituted aromatic 1,4-diazabuta-1,3-dienes afforded product of acetic acid addition to primary formed 1,3-dipole intermediate 5-(4-substituted phenylamino)-3-(4-substituted phenyl)-2-oxoimidazolidin-4-yl acetate.

Opis fizyczny
  • Department of Organic Chemistry, Faculty of Science, Masaryk University of Brno, Kotlářská 2, 611 37, Brno, Czech Republic,
  • Department of Organic Chemistry, Faculty of Science, Masaryk University of Brno, Kotlářská 2, 611 37, Brno, Czech Republic
  • [1] J. Verner, J. Taraba, M. Potáček: “A new route to 1,4-disubstituted 5-thioxoperhydroimidazo[4,5-d]imidazol-2-ones”, Tetrahedron Lett., Vol. 43 (27), (2002), pp. 4833–4836.[Crossref]
  • [2] J.R. Bailey, H.N. Moore: “Use of cyanic acid in glacial acetic acid. II. Addition of cyanic acid on benzalazine”, J. Am. Chem. Soc., Vol. 39, (1917), pp. 279–291.[Crossref]
  • [3] R. Grashey: Azomethine imines, In: A. Padwa (Ed.): 1,3-Dipolar Cycloaddition Chemistry, Wiley, New York, 1984, pp. 757–763.
  • [4] S. Rádl: “Crisscross Cycloaddition Reactions”, Aldrichimica Acta, Vol. 30, (1997), pp. 97–100.A.
  • [5] M. Sakamoto, Y. Tomimatsu, K. Miyazawa, K. Tokoro: “Reaction of conjugated systems containing nitrogen. IV. Reaction of conjugated 1,2-diimines with isocyanates”, Yakugaku Zasshi., Vol. 92 (12), (1972), pp. 1462–1467.
  • [6] M. Takahashi, S. Miyadai: “Synthesis of imidazo[4,5-d]imidazole-2,5-dithiones by crisscross addition reaction of 1,4-diaza-1,3-dienes to isothiocyanatotrimethylsilane”, Heterocycles, Vol. 31 (5), (1990), pp. 883–888.[Crossref]
  • [7] C.J. Broan, A.R. Butler, D. Reed, I.H. Sadler: “Mechanistic studies in the chemistry of thiourea. Part 1. Reaction with benzil under alkaline conditions”, J. Chem. Soc., Perkin Trans., Vol. 2, (1989), pp. 731–740. [Crossref]
  • [8] C.C. Cow, P.H.M. Harrison: “A Facile Preparation of Thioglycolurils from Glycolurils, and Regioselectivity in Thioglycoluril Template-directed Crossed-Claisen Condensations”, J. Org. Chem., Vol. 62 (25), (1997), pp. 8834–8840.[Crossref]
  • [9] Q. Long, G. Hong, G. Zuo, H. Ding, H. Youji: “Synthesis of 3,7-diimino-2,6-dithia-4,8-diazabicyclo-[3,3,0]octane and its derivatives”, Res. Inst. Chem. Eng., Vol. 3, (1982), pp. 170–175; Chem. Abstr., 1982, 562876.
  • [10] H. Pauly, H. Sauter: “Action of glyoxal on urea; new methods of formation of hydantoin”, Chem. Ber., Vol. 63, (1930), pp. 2063–2069. [Crossref]
  • [11] O.V. Lebedev, L.I. Khmel’nitskii, L.V. Epishina, L.I. Suvorova, I.V. Zaikonnikova, I.E. Zimakova, S.V. Kirshin, A.M. Karpov, V.S. Chudnovskii, et al.: The Directed Search for Neutropic Agents, Riga, 1983, pp. 81–93.
  • [12] H. Biltz, O. Behrens: “Action of Hypochlorous Acid and of Sodium Hypochlorite on Hydantoin and Acetylenediureins”, Ber. Vol. 43, (1910), pp. 1984–1996.
  • [13] J.W. Williams: U.S. Patent 1953, 2,649,389.
  • [14] H.B. Adkins: U.S. Patent 1953, 2,654,763.
  • [15] H. Petersen: “Syntheses of cyclic ureas by α-ureidoalkylation.”, Synthesis, (1973), pp. 243–292.
  • [16] J. Hofmann, G. Just, D. Moya, S. Ostermann, W. Pritzkow, M.P. Visothea: “Bleaching activators as acylating agents. Kinetics of the acetylation of piperidine by some bleaching activators”, J. Prakt. Chem., Vol. 332 (2), (1990), pp. 176–180.[Crossref]
  • [17] J. Hofmann, G. Just, W. Pritzkow, H.J. Schmidt: “Bleaching activators and the mechanism of bleaching activation”, J. Prakt. Chem., Vol. 334 (4), (1992), pp. 293–297.[Crossref]
  • [18] R.P. Sijbesma, R.J.M. Nolte: “Molecular clips and cages derived from glycoluril”, Topics Curr. Chem., Vol. 175, (1995), pp. 25–56.
  • [19] P.J. Cintas: “Cucurbituril: supramolecular perspectives for an old ligand”, J. Inclusion Phenom. Mol. Recognit. Chem., Vol. 17 (3), (1994), pp. 205–220.[Crossref]
  • [20] E. Weber: “Supramolecular Chemistry II- Host Design and Molecular Recognition”, Topics Curr. Chem., Vol. 175, (1995), pp. 164.
  • [21] R. Meissner, X. Garcias, S. Mecozzi, J. Jr. Rebek: “Synthesis and Assembly of New Molecular Hosts: Solvation and the Energetics of Encapsulation”, J. Am. Chem. Soc., Vol. 119 (1), (1997), pp. 77–85.[Crossref]
  • [22] D. Whang, K. Kim: “Polycatenated Two-Dimensional Polyrotaxane Net”, J. Am. Chem. Soc., Vol. 119 (2), (1997), pp. 451–452.[Crossref]
  • [23] O. Exner, J. M. Kliegman: “Dipole moments and conformations of 1,2-diimines”, J. Org. Chem., Vol. 36 (14), (1971), pp. 2014–2015.[Crossref]
  • [24] S. Leśniak: “Flash vacuum thermolysis of four-membered rings containing a nitrogen atom. Part V. Synthesis of glyoxal monoimines by thermal decomposition of 4-formylazetidin-2-ones”, Pol. J. Chem., Vol. 69 (11), (1995), pp. 1490–1496.
  • [25] R. Huisgen: “Kinetics and mechanism of 1,3-dipolar cycloadditions”, Angew. Chem., Vol. 75 (16/17), (1963), pp. 742–754.
  • [26] S. M. Mistry, P.C. Guha: “Aryldi- and poly-stibonic acids, distibinous oxides and distibino compounds”, J. Indian Inst. Sci. Sect. A, Vol. 15, (1932), pp. 25–40.
Typ dokumentu
Identyfikator YADDA
JavaScript jest wyłączony w Twojej przeglądarce internetowej. Włącz go, a następnie odśwież stronę, aby móc w pełni z niej korzystać.