Uncatalyzed and solvent-free multicomponent process for the synthesis of biphenyl-2-carbonitrile derivatives

Organic Letters

Volumn 8, Issue 25, 2006, Pages 5741-5744

  Fringuelli, Francesco ^a   Girotti, Rugiada ^a   Piermatti, Oriana ^a   Pizzo, Ferdinando ^a   Vaccaro, Luigi ^a  

^a UNIVERSITY OF PERUGIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; BIPHENYL DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; METAL; NITRILE; WATER;

ARTICLE; CHEMISTRY; CONFORMATION; INSTRUMENTATION; ORGANIC CHEMISTRY; SYNTHESIS; TEMPERATURE;

ALDEHYDES; BIPHENYL COMPOUNDS; CHEMISTRY, ORGANIC; INDICATORS AND REAGENTS; METALS; MOLECULAR CONFORMATION; NITRILES; TEMPERATURE; WATER;

EID: 33846307079     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062253o     Document Type: Article

References (20)

1. Bringmann, G.; Gunther, C.; Schupp, O.; Tesler S. In Progress in the Chemistry of Organic Natural Products; Herz, W., Falk, H., Kirby, G. W., Moore, R. E., Eds.; Springer-Verlag: New York, 2001; Vol. 81, pp 1-293.
2. (a) Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; De Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004.
3. (b) Cross-Coupling Reactions. A Practical Guide. In Top. Curr. Chem.; Miyaura, N., Ed.; Springer-Verlag: Berlin, 2002; Vol. 219.
4. Campeau, L.-C.; Fagnou, K. Chem. Commun. 2006, 1253-1264.
5. Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1-652.
6. Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359-1469.
7. Tsuji, J. Palladium Reagents and Catalysts: New Perspectives for the 21st Century; Wiley: Chichester, U.K., 2004.
8. Becht, J.-M.; Gissot, A.; Wagner, A.; Miosjkowki, C. Chem.-Eur. J. 2003, 9, 3209-3215.
9. As representative examples, see: (a) Fringuelli, F.; Pizzo, F.; Vaccaro, L. J. Org. Chem. 2004, 67, 2315-2321.
10. (b) Fringuelli, F.; Pizzo, F.; Tortoioli, S.; Vaccaro, L. Org. Lett. 2005, 7, 4411-4414 and literature cited therein.
11. As representative examples, see: (a) Fringuelli, F.; Pizzo, F.; Vittoriani, C.; Vaccaro, L. Chem. Commun. 2004, 2756-2757.
12. (b) Fringuelli, F.; Girotti, R.; Pizzo, F.; Vaccaro, L. Adv. Synth. Catal. 2006, 348, 297-300 and literature cited therein.
13. Noda, Y.; Akiba, Y.; Kashima, M. Synth. Commun. 1996, 26, 4633-4639.
14. (a) Zapf, A.; Ehrentraut, A.; Beller, M. Angew. Chem., Int. Ed. 2000. 39, 4153-4155.
15. (b) Yamada, Y. M. A.; Takeda, K.; Takahashi, H.; Ikegami, S. Org. Lett. 2002, 4, 3371-3374.
16. (c) Tewari, A.; Hein, M.; Zapf, A.; Beller, M. Synthesis 2004, 935-941.
17. (d) Wang, G. T. et al. Bioorg. Med. Chem. Lett. 2005, 15, 153-158.
18. General Procedure for the Preparation of Diels-Alder Adducts. A screw-capped vial equipped with a magnetic stirrer was charged with the aldehydes 1a-k, nitroacetonitrile 2 (1.5 molar equiv), and dienes 4a-c (2.0 molar equiv). The resulting mixture was left under magnetic stirring for the time and at the temperatures reported in Tables 1 and 2 and in Scheme 3. Cycloadducts 5a-n were isolated after silica gel column chromatography of the final mixture.
19. 2 (0.5 bar) under magnetic stirring at 60 °C for the time reported in Table 3 and Schemes 2 and 4. Biphenyls 6a-o were isolated after silica gel column chromatography of the final mixture.
20. Yamada, Y. M. A.; Takeda, K.; Takahashi, H.; Ikegami, S. Org. Lett. 2002, 4, 3371-3374 and literature cited therein.