Sinteza novih derivata benzotiazola s potencijalnim antitumorskim djelovanjem
| Autor: | Mamić, Antonija |
|---|---|
| Přispěvatelé: | Gazivoda Kraljević, Tatjana |
| Jazyk: | chorvatština |
| Rok vydání: | 2021 |
| Předmět: |
Huisgenova 1 3-dipolarna cikloadicija
Huisgen 1 3-dipolar cycloaddition 1 2 3-triazole 1 2 3-triazol mehanokemijske reakcije benzothiazole PRIRODNE ZNANOSTI. Kemija NATURAL SCIENCES. Chemistry benzotiazol microwave-assisted reaction benzotiazol Huisgenova 1 3-dipolarna cikloadicija 1 2 3-triazol klik reakcija mehanokemijske reakcije mikrovalovima potpomognute reakcije mikrovalovima potpomognute reakcije klik reakcija click reaction mechanochemical reactions |
| Popis: | U ovom radu je opisana sinteza novih 1,2,3-triazolnih derivata benzotiazola te njihova strukturna karakterizacija 1H- i 13C-NMR spektroskopijom. Mikrovalovima potpomognutom SN2 reakcijom 2-hidroksibenzaldehida i propargil-bromida uz K2CO3 kao bazu pripravljen je 2-(prop-2-in-1-iloksi)benzaldehid (1). Propargilirani derivat benzotiazola (2) priređen je ciklizacijom 2-O-propargilbenzaldehida (1) i ortho-aminotiofenola u dimetilformamidu uz oksidacijsko sredstvo Na2S2O5. Ciljani 1,2,3-triazolni derivati benzotiazola (3 – 14) sintetizirani su mehanokemijskim reakcijama Huisgenovom 1,3-dipolarnom cikloadicijom 2-(2-(prop-2-in-1-iloksi)fenil)benzo[d]tiazola (2) i odgovarajućih aromatskih azida uz bakrov(II) acetat kao katalizator. Strukture svih novopriređenih spojeva potvrđene su 1H- i 13C-NMR spektroskopijom. This paper describes the synthesis of new 1,2,3-triazolyl benzothiazole derivatives and their structural characterization by 1H- and 13C-NMR spectroscopy. Microwave-assisted SN2 reaction of 2-hydroxybenzaldehyde and propargyl bromide with K2CO3 as a base 2-(prop-2-yn-1-yloxy)benzaldehyde (1) was prepared. A propargylated benzothiazole derivative (2) was prepared by cyclization of 2-O-propargylbenzaldehyde (1) and ortho-aminothiophenol in dimethylformamide using Na2S2O5 as oxidizing agent. Target 1,2,3-triazolyl benzothiazole derivatives (3 - 14) were synthesized by mechanochemical reactions by Huisgen 1,3-dipolar cycloaddition of 2-(2-(prop-2-yn-1-yloxy)phenyl)benzo[d]thiazole (2) and the corresponding aromatic azides with copper (II) acetate as catalyst. The structures of all newly prepared compounds were confirmed by 1H- and 13C-NMR spectroscopy. |
| Databáze: | OpenAIRE |
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