A convenient synthesis of 3-amino-4-imino(thioxo)-imidazolidin-2-ones

Tetrahedron Letters

Volumn 45, Issue 38, 2004, Pages 7049-7051

  Kurz, Thomas ^a   Widyan, Khalid ^a  

^a UNIVERSITY OF HAMBURG   (Germany)

Author keywords

1,1 Carbonyldiimidazole; 1,1 Carbonyl di (1,2,4 triazole); 3 Amino 4 imino(thioxo) imidazolidin 2 ones; Diethylphosphonopropyl aminonitriles; Hydrazines

Indexed keywords

AMINE; HYDRAZINE DERIVATIVE; HYDROGEN SULFIDE; IMIDAZOLINE DERIVATIVE; IMINE; KETONE DERIVATIVE; NITRILE; THIOXYL DERIVATIVE;

ACIDITY; AMINO ACID SUBSTITUTION; ARTICLE; DRUG SYNTHESIS; HYDROLYSIS; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 4444357025     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.07.134     Document Type: Article

References (14)

1. L.J. Wilson, L. Min, and D.E. Portlock Tetrahedron Lett. 39 1998 5135 5138
2. I. Bélai Tetrahedron Lett. 44 2003 7475 7477
3. W.J. Brouilette, V.P. Jestkov, M.L. Brown, M.S. Akhtar, T.M. DeLorey, and G.M. Brown J. Med. Chem. 37 1994 3289 3293
4. E. Osz, L. Somsak, L. Sizilagyi, L. Kovacs, T. Docsa, B. Toth, and P. Gergely Bioorg. Med. Chem. Lett. 9 1999 1385 1390
5. S. He, R. Kuang, R. Venkataraman, J. Tu, T.M. Truong, H.T. Chan, and W.C. Groutas Bioorg. Med. Chem. 8 2000 1713 1717
6. M.-L. Lin, and C.-M. Sun Tetrahedron Lett. 44 2003 8739 8742
7. T. Kurz, D. Geffken, and K. Widyan Tetrahedron 60 2004 2409 2416
8. J.M. Varlet, G. Fabre, F. Sauveur, N. Collignon, and P. Savignac Tetrahedron 37 1981 1377 1384
9. Sternberg, J. A.; Adams, J. B. DuPont de Nemours, 1992; EP 503798, Chem. Abstr. 1993, 118, 80921u
10. Y. Kuroda, M. Okuhara, T. Goto, M. Okamoto, H. Terano, M. Kohsaka, H. Aoki, and H. Imanaka J. Antibiot. 33 1980 29 35
11. J.R. Morphy, N.R.A. Beeley, B.A. Boyce, J. Leonard, B. Mason, A. Millican, K. Millar, J.P. O'Connell, and J. Porter Bioorg. Med. Chem. Lett. 4 1994 2747 2752
12. 4, concentrated and the remaining oil was crystallized from EtOAc/hexane to give 4a-f,i,j as colorless solids. Due to its higher reactivity, CDT was used in case of α-aminonitriles derived from ketones.
13. 4P:C, 52.17; H, 6.84; N, 15.21. Found: C, 52.32; H, 6.94; N, 15.21
14. 4PS:C, 49.86; H, 6.28; N, 10.90. Found: C, 49.77; H, 6.37; N, 10.74