Synthesis of 2-[5-amino-2,3-dihydro-4H-imidazol-4-ylidene]malononitriles

Tetrahedron Letters

Volumn 47, Issue 9, 2006, Pages 1445-1447

  Eremkin, A V ^a   Ershov, O V ^a   Kayukov, Ya S ^a   Sheverdov, V P ^a   Nasakin, O E ^a   Tafeenko, V A ^b   Nurieva, E V ^b  

^a CHUVASH STATE UNIVERSITY   (Russian Federation)

^b MOSCOW STATE UNIVERSITY   (Russian Federation)

Author keywords

Carbonyl compounds; Cyano compounds; Heterocyclic compounds; Imidazoles

Indexed keywords

2 [5 AMINO 2,3 DIHYDRO 4H IMIDAZOL 4 YLIDENE]MALONONITRILE; MALONONITRILE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; X RAY CRYSTALLOGRAPHY;

EID: 31444452030     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.12.092     Document Type: Article

References (23)

1. J.P. Hielbe, W.E. Bondinell, and R.R. Ruffolo J. Med. Chem. 38 1995 3415
2. G.J. Molderings J. Hypertens. 15 Suppl. 1 1997 S9 S23
3. C.B. Chapleo, P.L. Myers, R.C.M. Butler, J.C. Doxey, A.G. Roach, and C.F.C. Smith J. Med. Chem. 26 1983 823
4. A. Carrieri, L. Brasili, F. Leonetti, M. Pigini, M. Giannella, P. Bousquet, and A. Carotti Bioorg. Med. Chem. 5 1997 843
5. A.L. Hudson, S. Husbands, J.W. Lewis, and D.J. Nutt Br. J. Pharmacol. 112 1994 S320
6. M.R. Grimmett Imidazole and Benzimidazole Synthesis 1997 Academic Press
7. Yamada, Y.; Zama, T.; Kurnashiro, I. Japanese Patent, 04,373, 1971; Chem. Abstr. 1971, 74, 125,693.
8. J.F.O. Connell, J. Parquette, W.E. Yelle, W. Wang, and H. Rapoport Synthesis 1988 767
9. Asai, N. German Patent 2,160,673, 1972; Chem. Abstr. 1972, 77, 114,409.
10. Y. Ohtsuka J. Org. Chem. 41 1976 713
11. Woodward, D. W. US Patent 2,534,331, 1950; Chem. Abstr. 1951, 45, 5191.
12. L. De Vries J. Org. Chem. 36 1971 3442
13. W.A. Sheppard, and O.W. Webster J. Am. Chem. Soc. 95 1973 2695
14. R.W. Begland, D.R. Hartter, F.N. Jones, D.J. Sam, W.A. Sheppard, O.W. Webster, and F.J. Weigert J. Org. Chem. 39 1974 2341
15. H. Bredereck, and G. Schmotzer Liebigs Ann. Chem. 600 1956 95
16. V.A. Tafeenko, K.A. Paseshnichenko, O.V. Ershov, A.V. Eremkin, and L.A. Aslanov Acta Crystallogr. C61 2005 o434 o437 Procedure for the preparation of 2-amino-1,1,2-tricyanoethylene (1 ). Tetracyanoethylene 0.64 g (0.005 mol) was added to a suspension of 0.97 g ammonium acetate in dioxane. After 20 min the solution was filtered, mixed with 0.02 ml of methyl iodide and then evaporated in vacuum. The residue was triturated in hexane and filtered, yielding 0.55 g (94%) of a solid compound
17. B.C. McKusick, R.E. Heckert, T.L. Cairns, D.D. Coffman, and H.F. Mower J. Am. Chem. Soc. 80 1958 2806 2815
18. W.J. Middleton, E.L. Little, D.D. Coffman, and V.A. Engelhardt J. Am. Chem. Soc. 80 1958 2795 2806
19. N.S. Zefirov, and D.I. Mahonkov Uspechi Chim. 49 1980 635
20. Typical procedure for the preparation of 2-[5-amino-2,3-dihydro-4H- imidazol-4-ylidene]malononitriles 3a-f : Method A. To 0.29 g (0.0025 mol) of 2-amino-1,1,2-ethylenetricarbonitrile in dioxane, 0.6 g of ammonium acetate and 0.0025 mol of the carbonyl compound were added. After 6 h, the reaction mixture was diluted with water and the resulting precipitate was isolated by filtration.
21. 5: C, 60.81; H, 6.96; N, 32.23. Found: C, 60.71; H, 6.85; N, 32.03.
22. Crystallographic data (excluding structure factors) for the structure in this paper (3a ) have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 285846. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK [fax: +44 (0) 1223 336033 or e-mail: http://deposit@ccdc.cam.ac.uk ].
23. One-pot procedure for preparation of 2-[5-amino-2,3-dihydro-4H-imidazol- 4-ylidene]malononitriles 3a-f : Method B. To 0.64 g (0.005 mol) of tetracyanoethylene in 5 ml of dioxane, 0.97 g of ammonium acetate and 0.005 mol of the carbonyl compound 2a-f were added. After 6 h, the reaction mixture was diluted with water and the resulting precipitate was isolated by filtration.