Study of the nucleophilic behaviour of N-phenylbenzamidine towards 1,2-diaza-1,3-dienes: Domino reactions for imidazole scaffolds

Tetrahedron

Volumn 66, Issue 27-28, 2010, Pages 5121-5129

  Attanasi, Orazio A ^a   Bartoccini, Silvia ^a   Giorgi, Gianluca ^b   Mantellini, Fabio ^a   Perrulli, Francesca R ^a   Santeusanio, Stefania ^a  

^a UNIVERSITY OF URBINO   (Italy)

^b UNIVERSITY OF SIENA   (Italy)

Author keywords

1,2 Diaza 1,3 dienes; Michael addition; Nitrogen heterocycles; Spiro compounds; Tautomerism

Indexed keywords

1,2 DIAZA 1,3 DIENE DERIVATIVE; ALKADIENE; ALLYL 1 [(METHOXYCARBONYL)AMINO] 5 METHYL 2 PHENYL 1H IMIDAZOLE 4 CARBOXYLATE; ALLYL 4 METHYL 1,2 DIPHENYL 1H IMIDAZOLE 5 CARBOXYLATE; BENZAMIDINE; ETHYL 1 [(ETHOXYCARBONYL)AMINO] 5 METHYL 2 PHENYL 1H IMIDAZOLE 4 CARBOXYLATE; ETHYL 1 [(METHOXYCARBONYL)AMINO] 5 METHYL 2 PHENYL 1H IMIDAZOLE 4 CARBOXYLATE; ETHYL 1 [(TERT BUTOXYCARBONYL)AMINO] 5 METHYL 2 PHENYL 1H IMIDAZOLE 4 CARBOXYLATE; ETHYL 2 ANILINO 7 [(ETHOXYCARBONYL)AMINO] 6 [2 (ETHOXYCARBONYL)HYDRAZINO] 6,8 DIMETHYL 4 OXO 1 PHENYL 1,3,7 TRIAZASPIRO[4,4]NONA 2,8 DIENE 9 CARBOXYLATE; ETHYL 2 ANILINO 7 [(METHOXYCARBONYL)AMINO] 6 [2 (METHOXYCARBONYL)HYDRAZINO] 6,8 DIMETHYL 4 OXO 1 PHENYL 1,3,7 TRIAZASPIRO[4,4]NONA 2,8 DIENE 9 CARBOXYLATE; ETHYL 2 ANILINO 7 [(TERT BUTOXYCARBONYL)AMINO] 6 [2 (TERT BUTOXYCARBONYL)HYDRAZINO] 6,8 DIMETHYL 4 OXO 1 PHENYL 1,3,7 TRIAZASPIRO[4,4]NONA 2,8 DIENE 9 CARBOXYLATE; ETHYL 2 [1 (2 ANILINO 4 OXO 1 PHENYL 4,5 DIHYDRO 1H IMIDAZOL 5 YL)ETHYLIDENE]HYDRAZINECARBOXYLATE; ETHYL 4 METHYL 1,2 DIPHENYL 1H IMIDAZOLE 5 CARBOXYLATE; ETHYL 7 [(METHOXYCARBONYL)AMINO] 6 [2 (METHOXYCARBONYL)HYDRAZINO] 6,8 DIMETHYL 4 OXO 1,2 DIPHENYL 1,3,7 TRIAZASPIRO[4.4]NONA 2,8 DIENE 9 CARBOXYLATE; ETHYL 7 [(TERT BUTOXYCARBONYL)AMINO] 6 [2 (TERT BUTOXYCARBONYL)HYDRAZINO] 6,8 DIMETHYL 4 OXO 1,2 DIPHENYL 1,3,7 TRIAZASPIRO[4.4]NONA 2,8 DIENE 9 CARBOXYLATE; IMIDAZOLE DERIVATIVE; ISOPROPYL 1 [(TERT BUTOXYCARBONYL)AMINO] 5 METHYL 2 PHENYL 1H IMIDAZOLE 4 CARBOXYLATE; ISOPROPYL 4 METHYL 1,2 DIPHENYL 1H IMIDAZOLE 5 CARBOXYLATE; METHYL 1 [(METHOXYCARBONYL)AMINO] 5 METHYL 2 PHENYL 1H IMIDAZOLE 4 CARBOXYLATE; METHYL 1 [(TERT BUTOXYCARBONYL)AMINO] 5 METHYL 2 PHENYL 1H IMIDAZOLE 4 CARBOXYLATE; METHYL 1 [[(BENZYLOXY)CARBONYL]AMINO] 5 METHYL 2 PHENYL 1H IMIDAZOLE 4 CARBOXYLATE; METHYL 2 ANILINO 7 [(METHOXYCARBONYL)AMINO] 6 [2 (METHOXYCARBONYL)HYDRAZINO] 6,8 DIMETHYL 4 OXO 1 PHENYL 1,3,7 TRIAZASPIRO[4,4]NONA 2,8 DIENE 9 CARBOXYLATE; METHYL 2 ANILINO 7 [(TERT BUTOXYCARBONYL)AMINO] 6 [2 (TERT BUTOXYCARBONYL)HYDRAZINO] 6,8 DIMETHYL 4 OXO 1 PHENYL 1,3,7 TRIAZASPIRO[4,4]NONA 2,8 DIENE 9 CARBOXYLATE; METHYL 2 [1 (2 ANILINO 4 OXO 1 PHENYL 4,5 DIHYDRO 1H IMIDAZOL 5 YL)ETHYLIDENE]HYDRAZINECARBOXYLATE; METHYL 2 [1 (5 OXO 2,3 DIPHENYL 3,5 DIHYDRO 4H IMIDAZOL 4 YLIDENE)ETHYL]HYDRAZINECARBOXYLATE; METHYL 4 METHYL 1,2 DIPHENYL 1H IMIDAZOLE 5 CARBOXYLATE; METHYL 7 [(METHOXYCARBONYL)AMINO] 6 [2 (METHOXYCARBONYL)HYDRAZINO] 6,8 DIMETHYL 4 OXO 1,2 DIPHENYL 1,3,7 TRIAZASPIRO[4.4]NONA 2,8 DIENE 9 CARBOXYLATE; METHYL 7 [(TERT BUTOXYCARBONYL)AMINO] 6 [2 (TERT BUTOXYCARBONYL)HYDRAZINO] 6,8 DIMETHYL 4 OXO 1,2 DIPHENYL 1,3,7 TRIAZASPIRO[4.4]NONA 2,8 DIENE 9 CARBOXYLATE; N PHENYLBENZAMIDINE; N5,N5 DIETHYL 4 METHYL 1,2 DIPHENYL 1H 5 IMIDAZOLECARBOXAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; DRUG SYNTHESIS; MICHAEL ADDITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; X RAY DIFFRACTION;

EID: 77954349750     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.04.108     Document Type: Article

References (25)

1. Chebanov, A. V.; Desenko, S. M.; Gurley, T. W. Azaheterocycles Based on a,b-Unsaturated Carbonyls; Springer: Berlin Heidelberg, 2008.
2. Jin, Z. Nat. Prod. Rep. 2009, 26, 382.
3. Grimmet, M. R. Imidazoles In. Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. W., Eds.; Pergamon: Oxford, 1996; Vol. 3.
4. De Luca, L. Curr. Med. Chem. 2006, 13, 1.
5. Bartroli, J.; Turmo, E.; Alguero, M.; Boncompte, E.; Vericat, M. L.; Conte, L.; Ramis, J.; Merlos, M.; Garcia-Rafanell, J.; Forn, J. J. Med. Chem. 1998, 41,1855.
6. Elliot, R. L.; Oliver, R. M.; LaFlamme, J. A.; Gillaspy, M. L.; Hammond, M.; Hank, R. F.; Maurer, T. S.; Baker, D. L.; DaSilva-Jardine, P. A.; Steveson, R. W.; Mack, C. M.; Cassella, J. V. Bioorg. Med. Chem. Lett. 2003, 13, 3593.
7. Street, J. P. Tetrahedron Lett. 1991, 32, 3333.
8. (a) Brasche, G.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 1932
9. (b) Abbiati, G.; Arcadi, A.; Canevari, V.; Rossi, E. Tetrahedron Lett. 2007, 48, 8491
10. (c) Yoburn, J. C.; Baskaran, S. Org. Lett. 2005, 7, 3801
11. (d) Guillemet, M.; Robert, A.; Baudy-Floc'h, M. Tetrahedron Lett. 1995, 36, 547
12. (e) Shilcrat, S. C.; Mokhallalati, M. K.; Fortunak, J. M. D.; Pridgen, L. N. J. Org. Chem. 1997, 62, 8449.
13. (a) Attanasi, O. A.; De Crescentini, L.; Favi, G.; Filippone, P.; Mantellini, F.; Per-rulli, F. R.; Santeusanio, S. Eur. J. Org. Chem. 2009, 3109
14. (b) Attanasi, O. A.; De Crescentini, L.; Filippone, P.; Mantellini, F.; Santeusanio, S. ARKIVOC 2002, xi.
15. Attanasi, O. A.; Giorgi, G.; Favi, G.; Filippone, P.; Lillini, S.; Perrulli, F. R.; San-teusanio, S. Synlett 2007, 1691.
16. (a) Hafelinger, G.; Fodor, G.; Phillips, B. A. In The Chemistry of Amidines and Imidates; Patai, S., Ed.; Wiley: New York, NY, 1975, Chapter 1-2
17. (b) Gautier, J.; Miocque, M.; Farnoux, C. C. In The Chemistry of Amidines and Imidates; Patai, S., Ed.; Wiley: New York, NY, 1975, Chapter 7.
18. Prevosek, D. C. J. Phys. Chem. 1962, 66, 769.
19. Clement, B.; Kampchen, T. Chem. Ber. 1986, 119, 1101.
20. Crystallographic data for compound 7a have been deposited with the Cambridge Crystallographic Data Centre with deposit number CCDC-745801. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data-request/cif (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +441223 336 033; or e-mail: deposit@ccdc.cam.ac.uk.
21. BratusekRecnik, S.; Svete, J.; Meden, A.; Stanovnik, B. Heterocycles 2003, 60, 1161.
22. Crystallographic data for compound 4e have been deposited with the Cambridge Crystallographic Data Centre with deposit number CCDC-745802. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data-request/cif (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: (+44) 1223-336-033; or e-mail: deposit@ ccdc.cam.ac.uk.
23. Crystallographic data compound 15a have been deposited with the Cambridge Crystallographic Data Centre with deposit number CCDC-745803. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data-request/cif (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336 033; or e-mail: deposit@ccdc.cam.ac.uk.
24. Sheldrick, G. M. SHELXS-97, A Program for Automatic Solution of Crystal Structures (Release 97-2); University of Gottingen: Gottingen, Germany, 1997.
25. Sheldrick, G. M. SHELXL-97, A Program for Crystal Structure Refinement (Release 97-2); University of Gottingen: Gottingen, Germany, 1997.