Ceric(IV) ammonium nitrate in the selective conversion of hydrazides to esters

Tetrahedron Letters

Volumn 40, Issue 23, 1999, Pages 4429-4432

  Štefane, Bogdan ^a   Kočevar, Marijan ^a   Polanc, Slovenko ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

Author keywords

Ceric(IV) ammonium nitrate; Esters; Hydrazides; Selective oxidation

Indexed keywords

CERIC IV AMMONIUM NITRATE; CERIUM NITRATE; HYDRAZIDE; THALLIUM; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; BIOTRANSFORMATION; CHEMICAL BINDING; CHEMICAL REACTION KINETICS; REACTION ANALYSIS; REACTION TIME; STRUCTURE ANALYSIS;

EID: 0033523056     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00764-9     Document Type: Article

References (24)

1. (a) Kepe, V.; Požgan, F.; Golobič, A.; Polanc, S.; Kočevar, M. J. Chem. Soc., Perkin Trans. 1 1998, 2813-2816.
2. (b) Košmrlj, J.; Kočevar, M.; Polanc, S. Synlett 1996, 652-654.
3. (c) Kočevar, M.; Mihorko, P.; Polanc, S. Synlett 1995. 241-242.
4. (d) Kočevar, M.; Susin, P.; Polanc, S. Synthesis 1993, 773-774.
5. Kočevar, M.; Mihorko, P.; Polanc, S. J. Org. Chem. 1995, 60, 1466-1469.
6. Štefane, B.; Kočevar, M.; Polanc, S. J. Org. Chem. 1997, 62, 7165-7169.
7. For recent reviews concerning various applications of CAN, see, for example: (a) Nair, V.; Mathew, J.; Prabhakaran, J. Chem. Soc. Rev. 1997, 26, 127-132.
8. (b) Molander, G. A. Chem. Rev. 1992, 92, 29-68.
9. (c) Kagan, H. B.; Namy, J. L. Tetrahedron 1986, 42, 6573-6614.
10. (d) Ho, T.-L. Organic Synthesis by Oxidation with Metal Compounds; Mijs, W. J., de Jonge, C. H. J., Eds.; Plenum: New York, 1986; pp 569-631.
11. Ho, T.-L.; Ho, C. H.; Wong, C. M. Synthesis 1972, 562-563.
12. Košmrlj, J.; Kočevar, M.; Polanc, S. J. Chem. Soc., Perkin Trans. 1 1998, 3917-3919.
13. It is known that hydrazides react with iodobenzene diacetate in the presence of methanol or ethanol leading to methyl or ethyl esters in moderate yields. This conversion of the hydrazide to the ester is usually accompanied by the formation of the corresponding acid and the isolation of the products requires column chromatography. See, Prakash, O.; Sharma, V.; Sadana, A. J. Chem. Res. (S) 1996, 100-101. For other oxidative transformations of hydrazides to acid derivatives see, for example, reference 2, and references cited therein.
14. (a) Tsuji, J.; Hayakawa., S.; Takayanagi, H. Chem. Lett. 1975, 437-438.
15. (b) Tsuji, J.; Nagashima, T.; Qui, N. T.; Takayanagi, H. Tetrahedron 1980, 36, 1311-1315.
16. 3: C, 67.52; H, 5.67; N, 6.06. Found: C, 67.44; H, 5.73; N, 5.99.
17. Ho, T.-L.; Wong, C. M. Synthesis 1972, 561-562.
18. Baciocchi, E.; Piermattei, A.; Ruzziconi, R. Synth. Commun. 1988, 18, 2167-2171.
19. All, M. H.; Leach, D. R.; Schmitz, C. E. Synth. Commun. 1998, 28, 2969-2981.
20. Ho, T.-L. Synth. Commun. 1979, 9, 237-239.
21. Riley, D. P.; Smith, M. R.; Correa, P. E. J. Am. Chem. Soc. 1988, 110, 177-180.
22. CAN was very recently applied to the selective removal of the dioxolane protecting group giving the appropriate keto-alcohol, the latter being extremely sensitive to acidic conditions. See, Ates, A.; Gautier, A.; Leroy, B.; Plancher, J.-M.; Quesnel, Y.; Markó, I. Tetrahedron Lett. 1999, 40, 1799-1802.
23. Tomioka, H.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1982, 23, 539-542.
24. Bag, A. K.; Gupta, S. R.; Dhar, D. N. Indian J. Chem., Sect. B 1986, 25, 433-434.