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Isomerisation of N-Acyl Benzylpenilloic Acid in Acetic Anhydride and Formation of 7, 7-Dimethyl-6-thia-3,8-diazahicyclo(3,2,1)octan-2-one

J. J. Herak ; Research Institute PLIVA, Zagreb, Croatia, Yugoslavia
M. Kovačević ; Research Institute PLIVA, Zagreb, Croatia, Yugoslavia
I. Lukić ; Research Institute PLIVA, Zagreb, Croatia, Yugoslavia
B. Gašpert ; Research Institute PLIVA, Zagreb, Croatia, Yugoslavia

Puni tekst: engleski, pdf (5 MB) str. 311-320 preuzimanja: 90* citiraj
APA 6th Edition
Herak, J.J., Kovačević, M., Lukić, I. i Gašpert, B. (1979). Isomerisation of N-Acyl Benzylpenilloic Acid in Acetic Anhydride and Formation of 7, 7-Dimethyl-6-thia-3,8-diazahicyclo(3,2,1)octan-2-one. Croatica Chemica Acta, 52 (3), 311-320. Preuzeto s https://hrcak.srce.hr/195894
MLA 8th Edition
Herak, J. J., et al. "Isomerisation of N-Acyl Benzylpenilloic Acid in Acetic Anhydride and Formation of 7, 7-Dimethyl-6-thia-3,8-diazahicyclo(3,2,1)octan-2-one." Croatica Chemica Acta, vol. 52, br. 3, 1979, str. 311-320. https://hrcak.srce.hr/195894. Citirano 28.07.2021.
Chicago 17th Edition
Herak, J. J., M. Kovačević, I. Lukić i B. Gašpert. "Isomerisation of N-Acyl Benzylpenilloic Acid in Acetic Anhydride and Formation of 7, 7-Dimethyl-6-thia-3,8-diazahicyclo(3,2,1)octan-2-one." Croatica Chemica Acta 52, br. 3 (1979): 311-320. https://hrcak.srce.hr/195894
Harvard
Herak, J.J., et al. (1979). 'Isomerisation of N-Acyl Benzylpenilloic Acid in Acetic Anhydride and Formation of 7, 7-Dimethyl-6-thia-3,8-diazahicyclo(3,2,1)octan-2-one', Croatica Chemica Acta, 52(3), str. 311-320. Preuzeto s: https://hrcak.srce.hr/195894 (Datum pristupa: 28.07.2021.)
Vancouver
Herak JJ, Kovačević M, Lukić I, Gašpert B. Isomerisation of N-Acyl Benzylpenilloic Acid in Acetic Anhydride and Formation of 7, 7-Dimethyl-6-thia-3,8-diazahicyclo(3,2,1)octan-2-one. Croatica Chemica Acta [Internet]. 1979 [pristupljeno 28.07.2021.];52(3):311-320. Dostupno na: https://hrcak.srce.hr/195894
IEEE
J.J. Herak, M. Kovačević, I. Lukić i B. Gašpert, "Isomerisation of N-Acyl Benzylpenilloic Acid in Acetic Anhydride and Formation of 7, 7-Dimethyl-6-thia-3,8-diazahicyclo(3,2,1)octan-2-one", Croatica Chemica Acta, vol.52, br. 3, str. 311-320, 1979. [Online]. Dostupno na: https://hrcak.srce.hr/195894. [Citirano: 28.07.2021.]

Sažetak
The heating of N-acyl benzylpenilloic acids {II) in a cetic
anhydride gave an equilibrium mixture of C-4 epimers, due to the
epimerisation at C-4 position. Cyclisation of the 2-amidomethyl and
4-carboxylic group of IIb or IIc into a 2-ketopiperazine ring gave
1S,5S or 1R,5R enantiomer of III. Alkaline hydrolysis of III gave
IV and II. When N-formyl group was present, IV and II upon acid
hydrolysis yielded V and I. The C-4 epimers (lb or le) can be
prepared from trans C-2, C-4 substituted C-4 epimers (Id or Ia)
via II and III.

Hrčak ID: 195894

URI
https://hrcak.srce.hr/195894

Posjeta: 159 *