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Chemistry of 1,3-Dioxepins. XII.' 4,7-Dihydro-5-nitro-1,3-dioxepins in the Diels-Alder Reaction with 4-Methyloxazole

Milena Jadrijević-Mladar Takač ; Department of Pharmaceutical Chemistry, Faculty of Pharmacy and Biochemistry, University of Zagreb, A. Kovačića 1, 10000 Zagreb, Croatia
Ivan Butula ; Department of Pharmaceutical Chemistry, Faculty of Pharmacy and Biochemistry, University of Zagreb, A. Kovačića 1, 10000 Zagreb, Croatia
Mladen Vinković ; PLIVA-Research Institute, Prilaz baruna Filipovića 25, 10000 Zagreb, Croatia
Miljenko Dumić ; PLIVA-Research Institute, Prilaz baruna Filipovića 25, 10000 Zagreb, Croatia

Puni tekst: engleski, pdf (8 MB) str. 649-666 preuzimanja: 141* citiraj
APA 6th Edition
Jadrijević-Mladar Takač, M., Butula, I., Vinković, M. i Dumić, M. (1997). Chemistry of 1,3-Dioxepins. XII.' 4,7-Dihydro-5-nitro-1,3-dioxepins in the Diels-Alder Reaction with 4-Methyloxazole. Croatica Chemica Acta, 70 (2), 649-666. Preuzeto s https://hrcak.srce.hr/176964
MLA 8th Edition
Jadrijević-Mladar Takač, Milena, et al. "Chemistry of 1,3-Dioxepins. XII.' 4,7-Dihydro-5-nitro-1,3-dioxepins in the Diels-Alder Reaction with 4-Methyloxazole." Croatica Chemica Acta, vol. 70, br. 2, 1997, str. 649-666. https://hrcak.srce.hr/176964. Citirano 02.03.2021.
Chicago 17th Edition
Jadrijević-Mladar Takač, Milena, Ivan Butula, Mladen Vinković i Miljenko Dumić. "Chemistry of 1,3-Dioxepins. XII.' 4,7-Dihydro-5-nitro-1,3-dioxepins in the Diels-Alder Reaction with 4-Methyloxazole." Croatica Chemica Acta 70, br. 2 (1997): 649-666. https://hrcak.srce.hr/176964
Harvard
Jadrijević-Mladar Takač, M., et al. (1997). 'Chemistry of 1,3-Dioxepins. XII.' 4,7-Dihydro-5-nitro-1,3-dioxepins in the Diels-Alder Reaction with 4-Methyloxazole', Croatica Chemica Acta, 70(2), str. 649-666. Preuzeto s: https://hrcak.srce.hr/176964 (Datum pristupa: 02.03.2021.)
Vancouver
Jadrijević-Mladar Takač M, Butula I, Vinković M, Dumić M. Chemistry of 1,3-Dioxepins. XII.' 4,7-Dihydro-5-nitro-1,3-dioxepins in the Diels-Alder Reaction with 4-Methyloxazole. Croatica Chemica Acta [Internet]. 1997 [pristupljeno 02.03.2021.];70(2):649-666. Dostupno na: https://hrcak.srce.hr/176964
IEEE
M. Jadrijević-Mladar Takač, I. Butula, M. Vinković i M. Dumić, "Chemistry of 1,3-Dioxepins. XII.' 4,7-Dihydro-5-nitro-1,3-dioxepins in the Diels-Alder Reaction with 4-Methyloxazole", Croatica Chemica Acta, vol.70, br. 2, str. 649-666, 1997. [Online]. Dostupno na: https://hrcak.srce.hr/176964. [Citirano: 02.03.2021.]

Sažetak
4,7-Dihydro-5-nitro-l,3-dioxepins 4' prepared by dehydrohalogenation
of vic-chloronitro-dioxepanes 2 and/or dehydrohalogenationdemercuration of vic-chloromercurynitro-dioxepanes 3 represent reactive dienophiles in the Diels-Alder cycloaddition with 4-methyloxazole (5), giving pyridoxine (8) intermediates 1,5-dihydro-9-hydroxy- 8-methyl-3H-[1,3]dioxepino[5,6-c]pyridines 6 in poor yields. The side products of this reaction were 4,7-dihydro-4-hydroxyimino- 6-nitro-l,3-dioxepins 7, the structure of which was confirmed by parallel synthesis, i.e. by nitrosation of 4 with ethyl nitrite. The order of reactivity in the series of 5-substituted-4, 7-dihydro- 1,3-dioxepins, calculated by AMI semiempirical method, is predicted to be 5-nitro- > 5-unsubstituted- > 5-cyano- > 5-chloro-4,7-dihydro- 1,3-dioxepin, and it is in agreement with experimental data.

Hrčak ID: 176964

URI
https://hrcak.srce.hr/176964

Posjeta: 221 *