Regioselective synthesis of 5-ylidenepyrrol-2(5H)-ones by reaction of transition metal-coordinated bis(imidoyl) chlorides with carbon nucleophiles

Journal of Organic Chemistry

Volumn 64, Issue 2, 1999, Pages 365-372

  Wuckelt, Jörg ^a   Döring, Manfred ^a   Langer, Peter ^b   Beckert, Rainer ^a   Görls, Helmar ^a  

^a FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

^b UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

(1 PHENYL 3 PHENYLAMINO 4 CARBOXYETHYL 2 OXOPYRROL 5 YLIDENE)DICARBOXYLIC ACID DIETHYL ESTER; (1 PHENYL 3 PHENYLAMINO 4 CYANO 2 OXOPYRROL 5 YLIDENE)CYANOACETIC ACID ETHYL ESTER; [1 (4 METHOXYPHENYL) 3 [(4 METHOXYPHENYL)AMINO] 4 CYANO 2 OXOPYRROL 5 YLIDENE]CYANOACETIC ACID ETHYL ESTER; [1 (4 NITROPHENYL) 3 [(4 NITROPHENYL)AMINO] 4 CARBOXYETHYL 2 OXOPYRROL 5 YLIDENE]DICARBOXYLIC ACID DIETHYL ESTER; [1 (4 TOLYL) 3 [(4 TOLYL)AMINO] 4 CARBOXYETHYL 2 OXOPYRROL 5 YLIDENE]DICARBOXYLIC ACID DIETHYL ESTER; [1 (4 TOLYL) 3 [(4 TOLYL)AMINO] 4 CYANO 2 OXOPYRROL 5 YLIDENE]CYANOACETIC ACID ETHYL ESTER; COBALT COMPLEX; MALONIC ACID DERIVATIVE; METAL COMPLEX; NICKEL COMPLEX; NITROGEN; OXALIC ACID DERIVATIVE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; COMPLEX FORMATION; CYCLIZATION; HYDROLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; X RAY DIFFRACTION;

EID: 0345369333     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9805910     Document Type: Article

References (41)

1. (a) Chiu, C. C.; Jordan, F. J. Org. Chem. 1994, 59, 5763-5766.
2. (b) Fabian, J.; Nakazumi, H.; Matsuoka, M. Chem. Rev. 1992, 92, 1197.
3. (a) Saalfrank, R. W.; Stark, A.; Bremer, M.; Hummel, H.-U. Angew. Chem. 1990, 102, 292; Angew. Chem., Int. Ed. Engl. 1990, 29, 311.
4. (a) Saalfrank, R. W.; Stark, A.; Bremer, M.; Hummel, H.-U. Angew. Chem. 1990, 102, 292; Angew. Chem., Int. Ed. Engl. 1990, 29, 311.
5. (b) Stachel, H.-D.; Schorp, M.; Maier, L.; Dandl, K. Liebigs Ann. Chem. 1994, 1121.
6. (a) Rao, Y. S. Chem. Rev. 1976, 76, 625.
7. (b) Pattenden, G. Fortschr. Chem. Org. Naturst. 1978, 35, 133.
8. (a) Johnson, L. K.; Killian, C. M.; Brookhart, M. J. Am. Chem. Soc. 1995, 117, 6414.
9. (b) Johnson, L. K.; Mecking, S.; Brookhart, M. J. Am. Chem. Soc. 1996, 118, 267.
10. (c) Killian, C. M.; Tempel, D. J.; Johnson, L. K.; Brookhart, M. J. Am. Chem. Soc. 1996, 118, 11664.
11. (d) Killian, C. M.; Johnson, L. K.; Brookhart, M. Organometallics 1997, 16, 2005.
12. (e) Abu-Surrah, A. S.; Rieger, B. Angew. Chem. 1996, 108, 2627; Angew. Chem., Int. Ed. Engl. 1996, 35, 2475.
13. (e) Abu-Surrah, A. S.; Rieger, B. Angew. Chem. 1996, 108, 2627; Angew. Chem., Int. Ed. Engl. 1996, 35, 2475.
14. (a) van Koten, G.; Vrieze, K. Adv. Organomet. Chem. 1982, 21, 151.
15. (b) Vrieze, K: J. Organomet. Chem. 1986, 300, 307.
16. (c) tom Dieck, H.; Dietrich, J. Chem. Ber. 1984, 117, 694.
17. For the reaction of delocalized dianions with bis(imidoyl) chlorides, see: (a) Langer, P.; Döring, M.; Görls, H.; Beckert, R. Liebigs Ann. / Receuil 1997, 2553.
18. (b) Langer, P.; Döring, M. Synlett 1998, 396.
19. (c) Langer, P.; Döring, M. Synlett 1998, 396.
20. (d) Langer, P.; Wuckelt, J.; Döring, M.; Beckert, R. Eur. J. Org. Chem. 1998, 1467.
21. Wuckelt, J.; Döring, M.; Langer, P.; Beckert, R.; Görls, H. Tetrahedron Lett. 1997, 5269.
22. Wuckelt, J.; Döring, M.; Langer, P.; Görls, H.; Beckert, R. Tetrahedron Lett. 1998, 1135.
23. The coordination of 3-amino-1-azadienes to transition metals is known to proceed readily: Villacorta, G. M.; Lippard, S. J. Pure Appl. Chem. 1986, 58, 1477.
24. Price, C. C.; Velzen, B. J. Org. Chem. 1946, 11, 6
25. The configurations of the isomers of 4c were generated and the energies were subsequently minimized using the MM+ force field which is implemented in release 3.0 of HyperChem. MM+ supplements the standard MM2 parameters (Allinger, N. L. J. Am. Chem. Soc. 1977, 99, 8127). All input geometries were taken from the molecule editor and optimized using the Polak-Ribiere algorithm. The minima obtained from the search were further optimized using the AM1 wave function (Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902) and the RHF approximation.
26. The configurations of the isomers of 4c were generated and the energies were subsequently minimized using the MM+ force field which is implemented in release 3.0 of HyperChem. MM+ supplements the standard MM2 parameters (Allinger, N. L. J. Am. Chem. Soc. 1977, 99, 8127). All input geometries were taken from the molecule editor and optimized using the Polak-Ribiere algorithm. The minima obtained from the search were further optimized using the AM1 wave function (Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902) and the RHF approximation.
27. Lindauer, D.; Beckert, R.; Döring, M.; Fehling, P.; Görls, H. J. Prakt. Chem., 1995, 337, 143.
28. Jameson, B.; Oswald, H. R.; Beer, H. R. J. Am. Chem. Soc. 1984, 106, 1669.
29. (a) Celmer, W. D.; Salomon, J. A. J. Am. Chem. Soc. 1955, 77, 2861.
30. (b) Simmons, C. J.; Marner, F.-J.; Cardellina, J. H., II; Moore, R. E.; Seff, K. Tetrahedron Lett. 1979, 2003.
31. (c) Abdullaev, N. D.; Samikov, K.; Antsupova, T. P.; Yagudaev, M. R.; Yunusov, S. Khim. Prir. Soedin 1987, 5, 692 [Chem. Nat. Compd. (Engl. Transl.) 1987, 23, 576].
32. (c) Abdullaev, N. D.; Samikov, K.; Antsupova, T. P.; Yagudaev, M. R.; Yunusov, S. Khim. Prir. Soedin 1987, 5, 692 [Chem. Nat. Compd. (Engl. Transl.) 1987, 23, 576].
33. (d) Falk, H.; Grubmayr, K.; Herzig, U.; Hofer, O. Tetrahedron Lett. 1975, 559.
34. (a) Knight, D. W.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 1979, 62.
35. (b) Pattenden, G. Fortschr. Chem. Org. Naturst. 1978, 35, 133.
36. (a) Gill, G. B.; James, G. D.; Oates, K. V.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 1993, 2567 and the following paper.
37. (b) Murakami, M.; Hayashi, M.; Ito, Y. J. Org. Chem. 1994, 59, 7910.
38. (c) Abell, A. D.; Oldham, M. D.; Taylor, J. M. J. Chem. Soc., Perkin Trans. 1 1995, 953.
39. MOLEN, An Interactive Structure Solution Procedure, Enraf-Nonius, Delft, The Netherlands, 1990.
40. Sheldrick, G. M. Acta Crystallogr. Sect. A 1990, 46, 467-473.
41. Sheldrick, G. M., University of Göttingen, Germany, 1993.