Synthesis and decarboxylation of N-acyl-α-triphenylphosphonio-α-amino acids: a new synthesis of α-(N-acylamino)alkyltriphenylphosphonium salts

Tetrahedron Letters

Volumn 49, Issue 11, 2008, Pages 1801-1803

  Mazurkiewicz, Roman ^a   Październiok Holewa, Agnieszka ^a   Grymel, Mirosława ^a  

^a SILESIAN UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

(N Acylamino)alkyltriphenylphosphonium salts; 4 Alkyl 4 triphenylphosphonio 5(4H) oxazolone hydrolysis; 4 Triphenylphosphoranylidene 5(4H) oxazolone hydrolysis; Decarboxylation; N Acyl triphenylphosphonio amino acids

Indexed keywords

ALPHA(N ACYLAMINO)ALKYLTRIPHENYLPHOSPHONIUM SALT DERIVATIVE; AMINO ACID DERIVATIVE; N ACYL ALPHA TRIPHENYLPHOSPHONIO ALPHA AMINO ACID DERIVATIVE; PHOSPHONIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL STRUCTURE; DECARBOXYLATION; HEATING; HYDROLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE; SYNTHESIS;

EID: 38949211093     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.01.051     Document Type: Article

References (20)

1. Mazurkiewicz R., Kuźnik A., Grymel M., and Październiok-Holewa A. Arkivoc VI (2007) 193-216
2. Mazurkiewicz R., and Pierwocha A. Monatsh. Chem. 127 (1996) 219-225
3. Mazurkiewicz R., and Pierwocha A. Monatsh. Chem. 128 (1997) 893-900
4. Drach B.S., Dolgushina I.Yu., and Sinitsa A.D. Zh. Obshch. Khim. 45 (1975) 1251-1255
5. Brovarets V.S., Lobanov O.P., and Drach B.S. Zh. Obshch. Khim. 53 (1983) 660-664
6. Brovarets V.S., Lobanov O.P., Kisilenko A.A., Kalinin V.N., and Drach B.S. Zh. Obshch. Khim. 56 (1986) 1492-1504
7. Brovarets V.S., Lobanov O.P., Vinogradova T.K., and Drach B.S. Zh. Obshch. Khim. 54 (1984) 288-301
8. Smolii O.B., Brovarets V.S., Pirozhenko V.V., and Drach B.S. Zh. Obshch. Khim. 58 (1988) 2635-2643
9. Smolii O.B., Brovarets V.S., and Drach B.S. Zh. Obshch. Khim. 56 (1986) 2802-2803
10. Smolii O.B., Brovarets V.S., Pirozhenko V.V., and Drach B.S. Zh. Obshch. Khim. 58 (1988) 2465-2471
11. Drach B.S., Sviridov E.P., and Kirsanov A.V. Zh. Obshch. Khim. 42 (1972) 953-954
12. Kozhushko B.N., Gumenyuk A.V., Palichuk Yu.A., and Shokol V.A. Zh. Obshch. Khim. 47 (1977) 333-339
13. Shokol V.A., Kozushko B.N., and Gumenyuk A.V. Zh. Obshch. Khim. 47 (1977) 1110-1118
14. Kasukhin L.F., Brovarets V.S., Smolii O.B., Kurg V.V., Budnik L.V., and Drach B.S. Zh. Obshch. Khim. 61 (1991) 2679-2684
15. Petersen H., and Reuther W. Justus Liebigs Ann. Chem. 766 (1972) 58-72
16. 3): δ 8.72 (dd, J = 6.7 Hz, J = 6.7 Hz, 1H), 7.76 (m, 15H), 6.18 (m, 1H)
17. 3, 5.1 mmol) were added. After 10 min, the solvent was evaporated under reduced pressure and the residue was crystallized from THF (3a and 3c) or chloroform (3b).
18. 2 and the pure product was precipitated by the addition of diethyl ether.
19. 2 and precipitating by means of addition of diethyl ether (4a-b).
20. 2 and precipitating by means of addition of diethyl ether (4e).