Sodium borohydride as the only reagent for the efficient reductive alkylation of malononitrile with ketones and aldehydes

Synthesis

Volumn , Issue 4, 2006, Pages 680-686

  Dunham, Jason C ^a   Richardson, Adam D ^a   Sammelson, Robert E ^a  

^a BALL STATE UNIVERSITY   (United States)

Author keywords

Aldehydes; Condensations; Ketones; Malononitrile; Reductions

Indexed keywords

ALDEHYDES; ALKYLATION; CONDENSATION; KETONES; REDUCTION; SYNTHESIS (CHEMICAL);

ISOPROPANOL; MALONONITRILES; MONOSUBSTITUTED DERIVATIVES; SODIUM BOROHYDRIDE;

SODIUM COMPOUNDS;

2 PROPANOL; ALDEHYDE; KETONE; MALONONITRILE; SODIUM BOROHYDRIDE;

ALKYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

EID: 33644499489     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-926307     Document Type: Article

References (33)

1. (a) Qian, F.; McCusker, J. E.; Zhang, Y.; Main, A. D.; Chlebowski, M.; Kokka, M.; McElwee-White, L. J. Org. Chem. 2002, 67, 4086.
2. (b) Bloomfield, J. J. J. Org. Chem. 1961, 26, 4112.
3. (a) Wu, Z.-L.; Li, Z.-Y. J. Org. Chem. 2003, 68, 2479.
4. (b) Meguro, M.; Yamamoto, Y. J. Org. Chem. 1999, 64, 694.
5. (c) Díez-Barra, E.; de la Hoz, A.; Moreno, A.; Sánchez-Verdú, P. J. Chem. Soc., Perkin Trans, 1 1991, 2589.
6. (a) Texier-Boullet, F.; Foucaud, A. Tetrahedron Lett. 1982, 23, 4927.
7. (b) Cabello, J. A.; Campelo, J. M.; Garcia, A.; Luna, D.; Marinas, J. M. J. Org. Chem. 1984, 49, 5195.
8. (c) Prout, F. S. J. Org. Chem. 1953, 18, 928.
9. (a) Garden, S. J.; Guimarães, C. R. W.; Corréa, M. B.; de Oliveira, C. A. F.; da Cunha Pinto, A.; de Alencastro, R. B. J. Org. Chem. 2003, 68, 8815.
10. (b) Zhang, B.; Zhu, X.-Q.; Lu, J.-Y.; He, J.; Wang, P. G.; Cheng, J.-P. J. Org. Chem. 2003, 68, 3295.
11. (c) Ranu, B. C.; Dutta, J.; Guchhait, S. K. Org. Lett. 2001, 3, 2603.
12. (d) Ranu, B. C.; Samanta, S. Tetrahedron 2003, 59, 7901.
13. Sammelson, R. E.; Allen, M. J. Synthesis 2005, 543.
14. Zhang, Z.; Gao, J.; Xia, J.-J.; Wang, G.-W. Org. Biomol. Chem. 2005, 3, 1617.
15. Brown, H. C.; Wheeler, O. H.; Ichikawa, K. Tetrahedron 1957, 1, 214.
16. Isolated yield for the previous one-pot method (ref. 5) was 83% and the reaction time was 10 min for the condensation step. The current yield was 78% in ≤6 min for both steps.
17. Chiriac, C. I.; Tanasa, F.; Onciu, M. Tetrahedron Lett. 2003, 44, 3579.
18. 4) only produces small amounts (ca. 20%) of condensation product after 24 h at r.t. when analyzed by TLC. For a recent report on the Knoevenagel condensation of malononitrile with aromatic aldehydes in EtOH without catalyst, see: Wang, X.-S.; Zeng, Z.-S.; Li, Y.-L.; Shi, D.-Q.; Tu, S.-J.; Wei, X.-Y.; Zong, Z.-M. Synth. Commun. 2005, 35, 1915.
19. Desai, U. V.; Pore, D. M.; Mane, R. B.; Solabannavar, S. B.; Wadgaonkar, P. P. Synth. Commun. 2004, 34, 25.
20. a = 7.3 in DMSO, see: Arnett, E. M.; Maroldo, S. G.; Schilling, S. L.; Harrelson, J. A. J. Am. Chem. Soc. 1984, 106, 6759.
21. a = 11.1 in DMSO, see: Matthews, W. S.; Bares, J. E.; Bartmess, J. E.; Bordwell, F. G.; Cornforth, F. J.; Drucker, G. E.; Margolin, Z.; McCallum, R. J.; McCollum, G. J.; Vanier, N. R. J. Am. Chem. Soc. 1975, 97, 7006.
22. (a) Okada, S.; Oohira, D.; Otaka, K. PCT Int. Appl. WO 2004020399, 2004; Chem. Abstr. 2004, 140, 235428.
23. (b) Otaka, T.; Ohira, D. Jpn. Kokai Tokkyo Koho JP 2004099597, 2004; Chem. Abstr. 2004, 140, 303517.
24. (c) Otaka, K.; Oohira, D.; Suzuki, M. PCT Int. Appl. WO 2002090321, 2002; Chem. Abstr. 2002, 137, 352788.
25. (d) Otaka, K.; Suzuki, M.; Oohira, D. PCT Int. Appl. WO 2002089579, 2002; Chem. Abstr. 2002, 137, 369842.
26. Yokoyama, M.; Kashiwagi, M.; Iwasaki, M.; Fuhshuku, K.; Ohta, H.; Sugai, T. Tetrahedron: Asymmetry 2004, 15, 2817.
27. 4 was added after 90 min.
28. Wada, M.; Mitsunobu, O. Tetrahedron Lett. 1972, 13, 1279.
29. Echevarria, A.; Martin, M.; Perez, C.; Rozas, I. Arch. Pharm. (Weinheim, Ger.) 1994, 327, 303.
30. Chikashita, H.; Nishida, S.; Miyazaki, M.; Morita, Y.; Itoh, K. Bull. Chem. Soc. Jpn. 1987, 60, 737.
31. Additional trimethylacetaldehyde was added after 60 min.
32. Bauer, T.; Thomann, R.; Mülhaupt, R. Macromolecules 1998, 31, 7651.
33. 4 was added after 20 min.