Citation: Wen-Yuan Tang, Jing-Jing Guo, Xing-Xing Gui, De-Man Han, Jian-Jun Li. An efficient synthesis of imidodicarbonic diamides from 1,3-thiazetidin-2-ones with NH2OH·HCl via ring-opening reaction[J]. Chinese Chemical Letters, ;2015, 26(1): 85-88. doi: 10.1016/j.cclet.2014.10.015 shu

An efficient synthesis of imidodicarbonic diamides from 1,3-thiazetidin-2-ones with NH2OH·HCl via ring-opening reaction

  • Corresponding author: Jian-Jun Li, 
  • Received Date: 8 July 2014
    Available Online: 9 October 2014

    Fund Project: We are grateful to the Natural Science Foundation of Zhejiang Province (No. LY13B020015) (No. LY13B020015)

  • A ring-opening process of 4-imino-1,3-thiazetidin-2-ones with NH2OH·HCl was described for the first time. Two different scaffolds of imidodicarbonic diamide were obtained selectively in good yields in the presence of organic base. The obtained imidodicarbonic diamides were demonstrated by X-ray diffraction analysis.
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    1. [1]

      [1] G.N. Rozentsveig, A.V. Popov, I.B. Rozentsveig, G.G. Levkovskaya, Reactions of N- (2,2,2-trichloroethylidene)- and N-(2,2-dichloro-2-phenylethylidene)arenesulfonamides with biuret, Russ. J. Org. Chem. 44 (2008) 1486-1489.

    2. [2]

      [2] C. Boss, M.H. Bolli, T. Weller, W. Fischli, M. Clozel, Bis-sulfonamides as endothelin receptor antagonists, Bioorg. Med. Chem. Lett. 13 (2003) 951-954.

    3. [3]

      [3] A. Sakakura, K. Suzuki, H. Katsuzaki, et al., Hanasanagin: a new antioxidative pseudo-di-peptide, 3,4-diguanidinobutanoyl-DOPA, from the mushroom, Isaria japonica, Tetrahedron Lett. 46 (2005) 9057-9059.

    4. [4]

      [4] Y.B. Chen, J.L. Li, X.S. Shao, X.Y. Xu, Z. Li, Design, synthesis and insecticidal activity of novel anthranilic diamides with benzyl sulfide scaffold, Chin. Chem. Lett. 24 (2013) 673-676.

    5. [5]

      [5] L. Kou, J. Liang, X.H. Ren, et al., Novel N-halamine silanes, Colloids Surf. A: Physicochem. Eng. Asp. 345 (2009) 88-94.

    6. [6]

      [6] H. Ito, K. Yumura, K. Saigo, Synthesis, characterization, and binding property of isoelectronic analogues of nucleobases, B(6)-substituted 5-aza-6-borauracils and -thymines, Org. Lett. 12 (2010) 3386-3389.

    7. [7]

      [7] M. Roman, B. Andrioletti, M. Lemaire, et al., Investigations providing a plausible mechanism in the hexamethyldisilazane-catalyzed trimerization of alkyl isocyanates, Tetrahedron 67 (2011) 1506-1510.

    8. [8]

      [8] Y. Sanemitsu, M. Shiroshita, K. Maeda, S. Inoue, A novel class of fungicides: 2H- 1,2,4,6-thiatriazine-3,5(4H,6H)-dione-1-oxides, Agric. Biol. Chem. 51 (1987) 3173-3175.

    9. [9]

      [9] R.R. Oltjen, E.E. Williams Jr., L.L. Slyter, G.V. Richardson, Urea versus biuret in a roughage diet for steers, J. Anim. Sci. 29 (1969) 816-822.

    10. [10]

      [10] F.J. Moore, E.S. Gatewood, The action of hydrogen peroxide upon certain phenylsubstituted uric acids, J. Am. Chem. Soc. 45 (1923) 135-145.

    11. [11]

      [11] C. Jin, C.W. Liu, W.K. Su, Novel synthesis of 2,4-dihydro-5-amino[1,2,4]triazol-3- ones from 1,3-disubstituted thioureas, Synlett (2009) 607-610.

    12. [12]

      [12] I.J. Enyedy, J. Wang, W.A. Zaman, K.M. Johnson, S. Wang, Discovery of substituted 3,4-diphenyl-thiazoles as a novel class of monoamine transporter inhibitors through 3-D pharmacophore search using a new pharmacophore model derived from mazindol, Bioorg. Med. Chem. Lett. 12 (2002) 1775-1778.

    13. [13]

      [13] K. Okuda, Y.X. Zhang, H. Ohtomo, T. Hirota, K. Sasaki, Polycyclic N-heterocyclic compounds. Part 62: reaction of N-(quinazolin-4-yl)amidine derivatives with hydroxylamine hydrochloride and anti-platelet aggregation activity of the products, Chem. Pharm. Bull. 58 (2010) 369-374.

    14. [14]

      [14] C.L. Carroll, A.R. Chamberlin, Synthesis of the dysiherbaine tetrahydrophran core utilizing improved tethered aminohydroxylation conditions, Tetrahedron Lett. 52 (2011) 3995-3997.

    15. [15]

      [15] V.Y. Sosnovskikh, V.S. Moshkin, R.A. Irgashev, Reactions of 3-(polyfluoroacyl)- chromones with hydroxylamine. The first synthesis of 3-cyano-2-(polyfluoroalkyl) chromones, Tetrahedron Lett. 47 (2006) 8543-8546.

    16. [16]

      [16] S. Man, M. Buchlovič, M. Potáček, Cyclization of β-allenyloximes as a novel method for nitrone preparation, Tetrahedron Lett. 47 (2006) 6961-6963.

    17. [17]

      [17] C. Pérez-Balado, B. Iglesias, L. Muñoz, Different reactivity of hydroxylamine with carbamoyl azides and carbamoyl cyanides: synthesis of hydroxyureas and carbamoyl amidoximes, J. Org. Chem. 75 (2010) 8039-8047.

    18. [18]

      [18] N. Poje, M. Poje, An unusual oxidative ring transformation of purine to imidazo[ 1,5-c]imidazole, Org. Lett. 5 (2003) 4265-4268.

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