1,4-Reductive Addition of Hydrazoic Acid

Synlett

Volumn 1996, Issue 4, 1996, Pages 341-342

  Couladouros, Elias A ^a   Apostolopoulos, Costas D ^a  

^a AGRICULTURAL UNIVERSITY OF ATHENS   (Greece)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0006583620     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5411     Document Type: Article

References (12)

1. Maciejewski, S.; Panfil, I.; Belzecki, C.; Chmielewski, M. Tetrahedron Lett., 1990, 31, 1901 and references cited therein.
2. Georgiadis M. P.; Apostolopoulos C. D.; Haroutounian S. A. J. Heterocyclic Chem., 1991, 28, 599.
3. Georgiadis M. P.; Haroutounian S. A.; Apostolopoulos C. D. Synthesis, 1991, 379.
4. Dal Pozzo A.; Acquasaliente M.; Dozelli G.; DeMaria P.; Nicoli C. J. Med. Chem., 1987, 30, 1674.
5. Kazmaier U. Angew. Chem. Int. Ed. Engl., 1994, 33, 998.
6. Mulzer J.; Schroder F.; Lobbia A.; Buschmann J.; Luger P. Angew. Chem. Int. Ed. Engl., 1994, 33, 1737.
7. 3 217.0739, found 217.0741. Detailed crystallographical data will be reported elsewhere.
8. Fieser L.; Hartwell J. J. Am. Chem. Soc., 1935, 57, 1482.
9. General experimental procedure for the preparation of compounds 3 : Lactone 2 is dissolved in methanol (0.2 M) and the solution is buffered with the addition of 1:1 mixture of AcOH:AcONa. A five fold excess of sodium azide is then added portionwise. After stirring for 6-8h at room temperature the reaction is extracted with ethyl acetate and the organic layers are washed with water, dried and concentrated under vacuum. Column chromatography purification affords 3-amino-2H-pyran-2,5(6H)-diones 3, in the yields shown in the Table.
10. a) Marcotte P.; Walsh C. Biochemistry, 1978, 17, 5613;
11. b) Guthrie, J. P. J. Am. Chem. Soc., 1972, 94, 7024; and
12. c) Wanjek H.; Nagel U.; Beck W. Chem. Ber., 1988, 121, 1021.