Comparing the traditional with the modern: A greener, solvent-free dihydropyrimidone synthesis

Journal of Chemical Education

Volumn 86, Issue 6, 2009, Pages 730-732

  Aktoudianakis, Evangelos ^a   Chan, Elton ^a   Edward, Amanda R ^a   Jarosz, Isabel ^a   Lee, Vicki ^a   Mui, Leo ^a   Thatipamala, Sonya S ^a   Dicks, Andrew P ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 67649976465     PISSN: 00219584     EISSN: None     Source Type: Journal    
DOI: 10.1021/ed086p730     Document Type: Article

References (36)

1. Tanaka, K. Solvent-Free Organic Synthesis; Wiley-VCH: Wein-heim, Germany, 2003.
2. Anastas, P. T.; Warner, J. C. Green Chemistry: Theory and Practice; Oxford University Press: New York, 1998; p 30.
3. U.S. Environmental Protection Agency: Twelve Principles of Green Chemistry, http://www.epa.gov/greencbemistry/pubs/principles.html (accessed Feb 2009).
4. Examples of recent educational organic syntheses under solvent-free conditions: (a) Cheney, M. L.; Zaworotko, M. J.; Beaton, S.; Singer, R. D. J. Chem. Educ. 2008, 55. 1649-1651.
5. (b) Nguyen, K. C.; Weizman, H. J. Chem. Educ. 2007, 84. 119-121.
6. (c) Esteb, J.J.; Hohman, J. N.; Schlamadinger, D.E.; Wilson, A. M. J. Chem. Educ. 2005, 82. 1837-1838.
7. (d) Cave, G. W. V.; Raston, C. L. J. Chem. Educ. 2005, 82. 468-469.
8. (e) Esteb, J. J.; Gligorich, K. M.; O'Reilly, S. A.; Richter, J. M. J. Chem. Educ. 2004, 81. 1794-1795.
9. (f) Leung, S. H.; Angel, S. A. J. Chem. Educ. 2004, 81. 1492-1493.
10. (g) Palleros, D. R. J. Chem. Educ. 2004, 81. 1345-1347.
11. (h) Barrett, J. A.; Esteb, J. J.; Hoops, G. C.; Richter, J. M. Chem. Educator [Online] 2004, 9. 30-31.
12. (i) Esteb, J. J.; Stockton, M. B. J. Chem. Educ. 2003, 80. 1446-1447.
13. (j) Esteb, J. J.; Schelle, M. W.; Wilson, A. M. J. Chem. Educ. 2003, 80. 907-908.
14. For textbook examples, see: (a) Doxsee, K. M.; Hutchison, J. E. Green Organic Chemistry: Strategies, Tools, And Laboratory Experiments; Thomson-Brooks/Cole: London, 2004.
15. (b) Greener Approaches to Undergraduate Chemistry Experiments; Kirchhoff, M., Ryan, M. A., Eds.; American Chemical Society: Washington, DC, 2002.
16. Biginelli, P. Gazz. Chim. Ital. 1893, 23. 360-413.
17. Folkers, K.; Harwood, H. J.; Johnson, T. B. J. Am. Chem. Soc. 1932, 54, 3751-3758.
18. Kappe, C. O. Eur. J. Med. Chem. 2000, 35. 1043-1052.
19. (a) Kappe, C. O. Acc. Chem. Res. 2000, 33. 879-888.
20. (b) Kappe, C. O. Tetrahedron 1993, 49. 6937-6963.
21. Holden, M. S.; Crouch, R. D. J. Chem. Educ. 2001, 78. 1104-1105.
22. Recent examples of Biginelli reactions catalyzed by Lewis acids under solvent-free conditions: (a) Chen, X.; Peng, Y. Cat. Lett. 2008, 122. 310-313.
23. (b) Adibi, H.; Samimi, H. A.; Beygzadeh, M. Cat. Commun. 2007, 8. 2119-2124.
24. (c) Singh, V.; Sapehiyia, V.; Srivastava, V.; Kaur, S. Cat. Commun. 2006, 7. 571-578.
25. (d) Kapoor, K. K.; Ganai, B. A.; Kumar, S.; Andotra, C. S. Can. J. Chem. 2006, 84. 433-437.
26. (e) De, S. K.; Gibbs, R. A. Synthesis 2005, 1748-1750.
27. (f) Zhang, G-L.; Cai, X-H. Synth. Commun. 2005, 35. 829-833.
28. Sun, Q.; Wang, Y.; Ge, Z.; Cheng, T.; Li, R. Synthesis 2004, 1047-1051.
29. Zhang, M.; Li, Y-Q. Synth. Commun. 2006, 36. 835-841.
30. Young, J. A. J. Chem. Educ. 2005, 82. 1770.
31. Young, J. A. J. Chem. Educ. 2008, 85. 1046.
32. Young, J. A. J. Chem. Educ. 2007, 84. 1421.
33. Bennett, G. D. J. Chem. Educ. 2006, 83. 1871-1872.
34. Trost, B. M. Science, 1991, 254. 1471-1477.
35. Andraos, J.; Sayed, M. J. Chem. Educ. 2007, 84. 1004-1010.
36. Greening Across the Chemistry Curriculum. Atom Economy: A Measure of the Efficiency of a Reaction. http://academic.scranton.edu/faculty/CANNMI/ organichtml (accessed Feb 2009).