Synthesis of 2-(arylamino)-2-(arylimino)acetamides

European Journal of Organic Chemistry

Volumn , Issue 5, 2004, Pages 1025-1032

  Langer, Peter ^a   Schroeder, Rita ^a  

^a UNIVERSITY OF GREIFSWALD   (Germany)

Author keywords

Amidines; Imidoyl chlorides; Oxalyl derivatives; Synthetic methods; Tautomerism

Indexed keywords

ACETAMIDE DERIVATIVE; ACETIC ACID DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; ELECTROSPRAY; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 4544388788     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300625     Document Type: Article

References (49)

1. Reviews: [1a] P. Langer, Chem. Eur. J. 2001, 7, 3858.
2. [1b] P. Langer, Synthesis 2002, 441.
3. [2a] For the cyclization of oxalyl chloride with 1,2-diols, see: T. Iida, T. Itaya, Tetrahedron 1993, 49, 10511.
4. [2b] For the synthesis of 1,2-diones, see: F. Babudri, V. Fiandanese, G. Marchese, A. Punzi, Tetrahedron Lett. 1995, 36, 7305.
5. [2c] For the synthesis of furan-2,3-diones, see: C. O. Kappe, G. Kollenz, C. Wentrup, Heterocycles 1994, 38, 779.
6. [2d] H. Ulrich, A. A. R. Sayigh, J. Org, Chem. 1965, 30, 2781.
7. [3a] C. Samarian, H.-W. Wanzlick, Tetrahedron Lett. 1974, 24, 2125, and references cited therein.
8. [3b] W. Trowitzsch, Justus Liebigs Ann. Chem. 1977, 1707.
9. [3c] C. C. Subramaniam, P. J. Thomas, V. R. Mamdapur, M. S. Chadha, Synthesis 1978, 468.
10. U. T. Mueller-Westerhoff, M. Zhou, J. Org. Chem. 1994, 59, 4988.
11. [5a] P. Langer, M. Stoll, Angew. Chem. 1999, 111, 1919; Angew. Chem. Int. Ed. 1999, 38, 1803.
12. [5a] P. Langer, M. Stoll, Angew. Chem. 1999, 111, 1919; Angew. Chem. Int. Ed. 1999, 38, 1803.
13. [5b] M. P. Sibi, M. Marvin, R. Sharma, J. Org. Chem. 1995, 60, 5016.
14. Review: P. Langer, M. Döring, Eur. J. Org. Chem. 2002, 221.
15. H. Hoppe, K. Hartke, Arch. Pharm. (Weinheim Ger.) 1975, 308, 526.
16. D. Lindauer, R. Beckert, M. Döring, P. Fehling, H. Görls, J. Prakt. Chem. 1995, 337, 143.
17. [9a] K. Hartke, H. Hoppe, Chem. Ber. 1974, 107, 3121.
18. [9b] K. Hartke, A. Kumar, J. Koester, G. Henssen, T. Kissel, Chem. Ber. 1982, 115, 3096.
19. [9c] K. Hartke, T. Gillmann, Liebigs Ann. Chem. 1986, 10, 1718.
20. [10a] C. C. Cjiu, P. Jordan, J. Org. Chem. 1994, 59, 5763, and references cited therein.
21. [10b] J. S. Nimitz, H. S. Mosher, J. Org. Chem. 1981, 45, 211.
22. [11a] V. N. Bodnar, M. O. Lozinskii, V. N. Kalinin, J. Org. Chem. USSR (Engl. Transl.) 1987, 23, 1991; Zh. Org. Khim. 1987, 23, 2252.
23. [11a] V. N. Bodnar, M. O. Lozinskii, V. N. Kalinin, J. Org. Chem. USSR (Engl. Transl.) 1987, 23, 1991; Zh. Org. Khim. 1987, 23, 2252.
24. [11b] V. A. Galishev, Yu. T. Struchkovu, T. S. Dolgushina, A. M. Shubnikov, K. A. Potekhin, Russ. J. Gen. Chem. 1996, 66, 558; Zh. Obshch. Khim. 1996, 66, 572.
25. [11b] V. A. Galishev, Yu. T. Struchkovu, T. S. Dolgushina, A. M. Shubnikov, K. A. Potekhin, Russ. J. Gen. Chem. 1996, 66, 558; Zh. Obshch. Khim. 1996, 66, 572.
26. [11c] R. Trave, L. Garanti, G. Zecchi, J. Chem. Soc., Perkin Trans. 1 1987, 1533.
27. [12a] R. Huisgen, F. Koch, Justus Liebigs Ann. Chem. 1955, 591, 200.
28. [12b] J. Barluenga, F. Fernandez-Mari, E. Aguilar, A. L. Viado, B. Olando, Tetrahedron Lett. 1998, 4887.
29. [12c] A. S. Shawali, A. A. Elghandour, S. M. El-Sheikh, J. Prakt. Chem. 2000, 342, 96.
30. [12d] G. Cusmano, G. Macaluso, W. Hinz, S. Buscemi, Heterocycles 1987, 26, 1283.
31. [12e] G. Heubach, Liebigs Ann. Chem. 1980, 1376.
32. [12f] C. A. Coda, G. Desimoni, G. A. Invernizzi, P. Quadrelli, P. P. Righetti, G. Tacconi, Tetrahedron 1987, 43, 2843.
33. [12g] A. Alemagna, P. del Buttere, E. Licandro, S. Maiorana, R. Trave, Tetrahedron 1984, 40, 935.
34. [12h] A. Ponti, G. Molteni, J. Org. Chem. 2001, 66, 5252.
35. [12i] D. A. Bowack, A. Lapworth, J. Chem. Soc. 1905, 87, 1854.
36. [13a] E. Csikos, C. Goenczi, B. Podanyi, G. Toth, I. Hermecz, J. Chem. Soc., Perkin Trans. 1 1999, 13, 1789.
37. [13b] J.-M. Coustard, Tetrahedron 1995, 57, 10929.
38. H. Klinger, Justus Liebigs Ann. Chem. 1876, 184, 261.
39. For synthetic approaches to 2-amino-2-iminoacetamides, see: [15a] From tetramethyl monoorthooxalate: R. Anschuetz, J. Stiepel, Justus Liebigs Ann. Chem. 1899, 306, 5;
40. from ethyl 2-chloro-2-iminoacetate: [15b] See ref.[14]
41. From methyl 2-anilino-2,2-dimethoxyacetate: [15c] G. D. Lander, J. Chem. Soc. 1907, 91, 967.
42. [15d] G. D. Lander, J. Chem. Soc. 1901, 79, 698.
43. For isolated examples of the use of a 2-amino-2,2-dichloroacetate, see: [15e] H. Klinger, Justus Liebigs Ann. Chem. 1876, 184, 280.
44. For a recent report on related hydrazones, see: G. Drutkowski, C. Donner, I. Schulze, P. Frohberg, Tetrahedron 2002, 58, 5317.
45. G. Scherer, H.-H. Limbach, J. Am. Chem. Soc. 1994, 116, 1230.
46. M. Wenzel, D. Lindauer, R. Beckert, R. Boese, E. Anders, Chem. Ber. 1996, 729, 39.
47. [19a] R. Beckert, R. Mayer, J. Prakt. Chem. 1982, 324, 227.
48. [19b] P. Fehling, M. Döring, F. Knoch, R. Beckert, H. Görls, Chem. Ber. 1995, 128, 405.
49. [19c] M. Döring P. Fehling, H. Görls, W. Imhof, R. Beckert, D. Lindauer, J. Prakt. Chem. 1999, 341, 748.