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Synthesis and Reactions of Some Azolecarboxylic Acid Derivatives

Igor Kalčić ; Faculty of Pharmacy and Biochemistry, A. Kovačića 1, 10 000 Zagreb, Croatia
Marijana Zovko ; Faculty of Pharmacy and Biochemistry, A. Kovačića 1, 10 000 Zagreb, Croatia
Milena Jadrijević-Mladar Takač ; Faculty of Pharmacy and Biochemistry, A. Kovačića 1, 10 000 Zagreb, Croatia
Branka Zorc ; Faculty of Pharmacy and Biochemistry, A. Kovačića 1, 10 000 Zagreb, Croatia
Ivan Butula ; Faculty of Pharmacy and Biochemistry, A. Kovačića 1, 10 000 Zagreb, Croatia

Puni tekst: engleski, pdf (146 KB) str. 217-228 preuzimanja: 1.222* citiraj
APA 6th Edition
Kalčić, I., Zovko, M., Jadrijević-Mladar Takač, M., Zorc, B. i Butula, I. (2003). Synthesis and Reactions of Some Azolecarboxylic Acid Derivatives. Croatica Chemica Acta, 76 (3), 217-228. Preuzeto s https://hrcak.srce.hr/103171
MLA 8th Edition
Kalčić, Igor, et al. "Synthesis and Reactions of Some Azolecarboxylic Acid Derivatives." Croatica Chemica Acta, vol. 76, br. 3, 2003, str. 217-228. https://hrcak.srce.hr/103171. Citirano 15.11.2019.
Chicago 17th Edition
Kalčić, Igor, Marijana Zovko, Milena Jadrijević-Mladar Takač, Branka Zorc i Ivan Butula. "Synthesis and Reactions of Some Azolecarboxylic Acid Derivatives." Croatica Chemica Acta 76, br. 3 (2003): 217-228. https://hrcak.srce.hr/103171
Harvard
Kalčić, I., et al. (2003). 'Synthesis and Reactions of Some Azolecarboxylic Acid Derivatives', Croatica Chemica Acta, 76(3), str. 217-228. Preuzeto s: https://hrcak.srce.hr/103171 (Datum pristupa: 15.11.2019.)
Vancouver
Kalčić I, Zovko M, Jadrijević-Mladar Takač M, Zorc B, Butula I. Synthesis and Reactions of Some Azolecarboxylic Acid Derivatives. Croatica Chemica Acta [Internet]. 2003 [pristupljeno 15.11.2019.];76(3):217-228. Dostupno na: https://hrcak.srce.hr/103171
IEEE
I. Kalčić, M. Zovko, M. Jadrijević-Mladar Takač, B. Zorc i I. Butula, "Synthesis and Reactions of Some Azolecarboxylic Acid Derivatives", Croatica Chemica Acta, vol.76, br. 3, str. 217-228, 2003. [Online]. Dostupno na: https://hrcak.srce.hr/103171. [Citirano: 15.11.2019.]

Sažetak
Reaction of several azoles with phosgene or triphosgene was studied. Besides benzotriazole (previously described reaction), only indazole, 5-nitroindazole and 5-methylbenzotriazole gave the corresponding 1-azolecarbonyl chlorides 1a-d. Azoles of weak acidity (imidazole, 1,2,3-triazole, 1,2,4-triazole, benzimidazole) could not give stable acyl chlorides, while strong acidic azoles like tetrazole and 4,5,6,7-tetrachlorobenzotriazole did not react at all. Chlorides 1b-d readily reacted with alcohols, amines, amino acids and their esters like the previously described 1-benzotriazolecarboxylic acid chloride (1a), giving 1-azolecarboxylic acid esters (2) or amides (3), N-(1-azolecarbonyl)amino acids (4, 5), their esters (8, 9) or amides (10, 11). However, a significant difference was observed in the reactivity of azole derivatives 2-11 with amines, alcohols and N-protected amino acids or in their stability in acidic and basic aqueous media. Benzotriazole and methylbenzotriazole derivatives were more reactive than indazole or nitroindazole derivatives. The higher reactivity was in correlation with the shift of the IR carbonyl absorption band to higher wave numbers.

Ključne riječi
azole; benzotriazole; indazole; 5-nitroindazole; 5-methylbenzotriazole; azolecarbonyl chloride; reaction with; synthesis

Hrčak ID: 103171

URI
https://hrcak.srce.hr/103171

Posjeta: 1.400 *