Synthesis of azines in solid state: Reactivity of solid hydrazine with aldehydes and ketones

Organic Letters

Volumn 13, Issue 24, 2011, Pages 6386-6389

  Lee, Byeongno ^a   Hyung Lee, Kyu ^a   Cho, Jaeheung ^b   Nam, Wonwoo ^b   Hur, Nam Hwi ^a  

^a Sogang University   (South Korea)

^b Ewha Womans University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; AZO COMPOUND; HYDRAZINE DERIVATIVE; KETONE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; SYNTHESIS;

ALDEHYDES; AZO COMPOUNDS; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; HYDRAZINES; KETONES; MOLECULAR STRUCTURE;

EID: 84055224047     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol202593g     Document Type: Article

References (37)

1. (a) André, V.; Hardeman, A.; Halasz, I.; Stein, R. S.; Jackson, G. J.; Reid, D. G.; Duer, M. J.; Curfs, C.; M. Duarte, T.; Frišč ić, T. Angew. Chem., Int. Ed. 2011, 50, 7858-7861.
2. (b) Atkinson, M. B. J.; Santhana Mariappan, S. V.; Bučar, D.-K.; Baltrusaitis, J.; Friščić, T.; Sinada, N. G.; MacGillivray, L. R. Proc. Natl. Acad. Sci. U.S.A. 2011, 108, 10974-10979.
3. (c) Friščić, T.; Reid, D. G.; Halasz, I.; Stein, R. S.; Dinnebier, R. E.; Duer, M. J. Angew. Chem., Int. Ed. 2010, 49, 712-715.
4. (d) Friščić T.; Jones, W. Cryst. Growth Des. 2009, 9, 1621-1637.
5. (e) Sankaranarayanan, J.; Bort, L. N.; Mandel, S. M.; Chen, P.; Krause, J. A.; Brooks, E. E.; Tsang, P.; Gudmundsdottir, A. D. Org. Lett. 2008, 10, 937-940.
6. (f) Atkinson, M. B. J.; Bučar, D.-K.; Sokolov, A. N.; Friščić, T.; Robinson, C. N.; Bilal, M. Y.; Sinada, N. G.; Chevannes, A.; MacGillivray, L. R. Chem. Commun. 2008, 5713-5715.
7. (g) Yoshida, J.; Nishikiori, S.-i.; Kuroda, R. Chem.;Eur. J. 2008, 14, 10570-10578.
8. (h) Adams, C. J.; Colquhoun, H. M.; Crawford, P. C.; Lusi, M.; Orpen, A. G. Angew. Chem., Int. Ed. 2007, 46, 1124-1128.
9. (i) Lazuen-Garay, A.; Pichon, A.; James, S. L. Chem. Soc. Rev. 2007, 36, 846-855.
10. (j) Bonneau, P. R.; Jarvis, R. F., Jr; Kaner, R. B. Nature 1991, 349, 510-512.
11. Toda, F., et al. Organic Solid State Reactions; Springer-Verlag: Berlin, Heidelberg: 2005 and references cited therein.
12. (a) Chattopadhyay, G.; Ray, P. S. Synth. Commun. 2011, 41, 2607-2614.
13. (b) Safari, J.; Gandomi-Ravandi, S. Synth. Commun. 2011, 41, 645-651.
14. (c) Eshghi, H.; Hosseini, M. J. Chin. Chem. Soc. 2008, 55, 636-638.
15. (d) Kaupp, G.; Schmeyers, J. J. Phys. Org. Chem. 2000, 13, 388-394.
16. (e) Toda, F.; Hyoda, S.; Okada, K.; Hirotsu, K. Chem. Commun. 1995, 1531-1532.
17. West, A. R. Solid State Chemistry and its Applications; John Wiley& Sons (SEA) Pte. Ltd.: Singapore, 1989.
18. Lee, B.; Kang, S. H.; Kang, D.; Lee, K. H.; Cho, J.; Nam, W.; Han, O. H.; Hur, N. H. Chem. Commun. 2011, 47, 11219-11221.
19. (a) Tang, W.; Xiang, Y.; Tong, A. J. Org. Chem. 2009, 74, 2163-2166.
20. (b) Rajendiran, N.; Balasubramanian, T. Spectrochim. Acta, Part A 2007, 68, 894-904.
21. (c) Lewis, M.; Glaser, R. J. Org. Chem. 2002, 67, 1441-1447.
22. (d) Chen, G. S.; Wilbur, J. K.; Barnes, C. L.; Glaser, R. J. Chem. Soc., Perkin Trans. 2 1995, 2311-2317.
23. (e) Nalwa, H. S.; Kakuta, A.; Mukoh, A. J. Appl. Phys. 1993, 73, 4743-4745.
24. (a) Kurteva, V. B.; Simeonov, S. P.; Stoilova-Disheva, M. Pharmacol. Pharm. 2011, 2, 1-9.
25. (b) Gǎinǎ, L.; Csámpai, A.; Túrós, G.; Lovász, T.; Zsoldos-Mády, V.; Silberg, I. A.; Sohár, P. Org. Biomol. Chem. 2006, 4, 4375-4386.
26. (c) Kuznetsova, Y. A.; Romakh, V. B. Appl. Biochem. Biotechnol. 1996, 61, 205-209.
27. (a) Cianga, I.; Ivanoiu, M. Eur. Polym. J. 2006, 42, 1922-1933.
28. (b) Euler, W.B.; Cheng, M.; Zhao, C. Chem. Mater. 1999, 11, 3702-3708.
29. (c) Kesslen, E. C.; Euler, W. B. Chem. Mater. 1999, 11, 336-340.
30. (d) Euler, W. B. Chem. Mater. 1990, 2, 209-213.
31. (a) Nanjundaswamy, H. M.; Pasha, M. A. Synth. Commun. 2007, 37, 3417-3420.
32. (b) Cohen, R.; Rybtchinski, B.; Gandelman, M.; Shimon, L. J. W.; Martin, J. M. L.; Milstein, D. Angew. Chem., Int. Ed. 2003, 42, 1949-1952.
33. (c) Chen, G. S.; Anthamatten, M.; Barnes, C. L.; Glaser, R. J. Org. Chem. 1994, 59, 4336-4340.
34. (d) Ferguson, L. N.; Goodwin, T. C. J. Am. Chem. Soc. 1949, 71, 633-637.
35. Precaution. The solid hydrazine, hydrazinium carboxylate (1), could be harmful for health due to its sublimation character. The equipment of effective ventilation is highly recommended for handling the solid hydrazine to avoid vapor inhalation.
36. Patai, S. The Chemistry of the Carbon-Nitrogen Double Bond; Interscience Publisher: London, 1970; pp 64-65.
37. Chen, X.-H. Acta Crystallogr. 2007, E63, o4443.