Formation of γ-oxoacids and 1 H-pyrrol-2(5 H)-ones from α,β-unsaturated ketones and ethyl nitroacetate

Journal of Organic Chemistry

Volumn 75, Issue 21, 2010, Pages 7435-7438

  Aginagalde, Maialen ^a   Bello, Tamara ^a   Masdeu, Carme ^b   Vara, Yosu ^b   Arrieta, Ana ^a   Cossío, Fernando P ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

^b Ikerchem Ltd   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

COMPUTATIONAL RESULTS; ETHYL NITROACETATE; HYDROLYTIC CONDITIONS; KETOACIDS; MICHAEL ADDITIONS; OXO-ACIDS; PRIMARY AMINES; UNSATURATED KETONES;

ADDITION REACTIONS; CARBOXYLATION;

KETONES;

2 (4 METHOXYPHENYL) 4 OXO 4 PHENYLBUTANOIC ACID; 3 (4 METHOXYPHENYL) 5 PHENYL 1,5 DIHYDRO 2H PYRROL 2 ONE; ACETIC ACID DERIVATIVE; AMINE; CARBOXYLIC ACID DERIVATIVE; DIAMINO ACID; ETHYL 2 (4 METHOXYPHENYL) 4 OXO 4 PHENYLBUTANOATE; ETHYL NITROACETATE; GAMMA KETOACID; KETONE DERIVATIVE; OXOACID; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; DECARBOXYLATION; DENSITY FUNCTIONAL THEORY; HYDROLYSIS; MICHAEL ADDITION; MICROWAVE IRRADIATION; OXIDATION; REACTION TIME; SYNTHESIS;

ACETATES; ACIDS; KETONES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NITRO COMPOUNDS; OXYGEN; PYRROLES;

EID: 78049525239     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101388x     Document Type: Article

References (39)

1. Mooney, B. P.; Miernyk, J. A.; Randall, D. D. Annu. Rev. Plant Biol. 2002, 53, 357-375
2. Cole, P. A. Nat. Chem. Biol. 2008, 4, 590-597
3. Ng, S. S.; Kavanagh, K. L.; McNough, M. A.; Butler, D.; Pilka, E. S.; Llenara, B. M. R.; Bray, J. E.; Savitsky, P.; Gileadi, O.; van Delft, F.; Rose, N. R.; Offer, J.; Scheinost, J. C.; Oppermann, V. Nature 2007, 448, 87-91
4. Cho, C.-C.; Liu, J.-N.; Chien, C.-H.; Shie, J.-J.; Chen, Y.-C.; Fang, J.-M. J. Org. Chem. 2009, 74, 1549-1556
5. Sanki, A. K.; Talan, R. S.; Sucheck, S. J. J. Org. Chem. 2009, 74, 1886-1896
6. Fukuzumi, T.; Bode, J. W. J. J. Am. Chem. Soc. 2009, 131, 3864-3865
7. Gooβen, L. S.; Rudolphi, F.; Oppel, C.; Rodríguez, N. Angew. Chem., Int. Ed. 2008, 47, 3043-3045
8. Hume, W. E.; Tokunaga, T.; Nagata, R. Tetrahedron 2002, 58, 3605-3611
9. Marziano, N. C.; Ronchin, L.; Tortato, C.; Ronchin, S.; Vavasori, A. J. Mol. Catal. A.: Chem. 2005, 235, 26-34
10. Zubia, A.; Ropero, S.; Otaegui, D.; Ballestar, E.; Fraga, M. F.; Boix-Chornet, M.; Berdasco, M.; Martinez, A.; Coll-Mulet, L.; Cossío, F. P.; Esteller, M. Oncogene 2009, 28, 1477-1484
11. Arrieta, A.; Otaegui, D.; Zubia, A.; Cossío, F. P.; Díaz-Ortiz, A.; de la Hoz, A.; Herrero, M. A.; Prieto, P.; Foces-Foces, C.; Pizarro, J. L.; Arriortua, M. I. J. Org. Chem. 2007, 72, 4313-4322
12. Zubia, A.; Mendoza, L.; Vivanco, S.; Aldaba, E.; Carrascal, T.; Lecea, B.; Arrieta, A.; Zimmerman, T.; Vidal-Vanaclocha, F.; Cossío, F. P. Angew. Chem., Int. Ed. 2005, 44, 2903-2907
13. Ballini, R.; Petrini, M. Tetrahedron 2004, 60, 1017-1047
14. Ballini, R.; Marcantoni, E.; Petrini, E.; Rosini, G. Synthesis 1988, 915-917
15. Ballini, R.; Bosica, G.; Fiorni, D.; Palmieri, A.; Petrini, M. Chem. Rev. 2005, 105, 933-971
16. Iida, H.; Morozimato, T.; Hamana, H.; Matsumoto, K. Tetrahedron Lett. 2007, 48, 2037
17. Olah, G. A.; Arvanagui, M.; Vankar, Y. D.; Surya Prakash, G. K. Synthesis-Stuttgart 1980, 662
18. CCDC 770165 and CCDC 770164 contain the supplementary crystallographic data for compounds 3a and 4b, respectively. These data can be obtained free of charge via www.ccdc.ac.uk/data-requestcif, by emailing data-request@ccdc.com.ac. uk or by contacting The Cambridge Cristallography Data Centre, 12 Union Rd, Cambridge CB2 1EZ, UK; fax +44 1223 336033.
19. For a related example see: Milne, C.; Powell, A.; Jim, J.; Al Nakeed, M.; Smith, C. P.; Micklefield, J. J. Am. Chem. Soc. 2006, 128, 11250-11259
20. The DFT calculations were carried out using the B3LYP hybrid functional and the 6311++G* basis set. Solvent conditions (MeOH) were considered by means of the PCM method. See: Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
21. Lee, C.; Yane, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
22. Raghavachari, K.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650-654
23. Tomasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005, 105, 2999-3093
24. Frisch, M. J. Gaussian09, revision A.02; Gaussian, Inc., Wallinford, CT, 2009. (Full reference is given in the Supporting Information.)
25. Hratchian, H. P.; Schlegel, H. B. J. Chem. Phys. 2004, 120, 9918-9924
26. Hratchian, H. P.; Schlegel, H. B. J. Chem. Theory Comput. 2005, 1, 61-69
27. For pioneering, although conceptually different methodologies for the preparation of these compounds see: Moon, M. W. J. Org. Chem. 1977, 42, 2219-2223
28. Shin, C.; Yonezawa, Y.; Watanabe, E. Tetrahedron Lett. 1985, 26, 85-88 See also ref 17.
29. See for example: Snider, B. B.; Neubert, B. J. J. Org. Chem. 2004, 69, 8952-8955
30. Gouault, N.; Le Roch, M.; Cornée, C.; David, M.; Uriac, P. J. Org. Chem. 2009, 74, 5614-5617
31. Rosas, N.; Sharma, P.; Arellano, I.; Ramírez, M.; Pérez, M.; Hernández, S.; Cabrera, A. Organometallics 2005, 24, 4893-4895
32. Shiraki, R.; Sumino, A.; Tadano, K.; Ogawa, S. Tetrahedron Lett. 1995, 36, 5551-5554
33. Grison, C.; Genève, S.; Coutrot, P. Tetrahedron Lett. 2001, 42, 3831-3834
34. Green, M. P.; Prodger, J. C.; Hayes, C. J. Tetrahedron Lett. 2002, 43, 6609-6611
35. Murai, M.; Miki, K.; Ohe, K. J. Org. Chem. 2008, 73, 9174-9176
36. Shiraki, R.; Sumino, A.; Tadano, K.; Ogawa, S. J. Org. Chem. 1996, 61, 2845-2852
37. Dittami, J. P.; Xu, F.; Qi, H.; Martin, N. W.; Bordner, J.; Decosta, D. L.; Kiplinger, J.; Reiche, J.; Ware, R. Tetrahedron Lett. 1995, 36, 4201-4204
38. Green, M. P.; Prodger, J. C.; Hayes, C. J. Tetrahedron Lett. 2002, 43, 2649-2652
39. For a related reaction leading to ethyl 2,5-disubstituted-1 H -pyrrole-3-carboxylates see: Minetto, G.; Raveglia, L. F.; Sega, A.; Taddei, M. Eur. J. Org. Chem. 2005, 5277-5288