Preparation of novel nitro-substituted benzothiazole derivatives
| Autor: | Petanjko, Monika |
|---|---|
| Přispěvatelé: | Raić-Malić, Silvana |
| Jazyk: | chorvatština |
| Rok vydání: | 2022 |
| Předmět: |
„click“ reaction
1 2 3-1H-triazoli Huisgenova cikloadicija mehanokemijska sinteza nitro-substituted benzothiazoles benzothiazole mechanochemical synthesis PRIRODNE ZNANOSTI. Kemija NATURAL SCIENCES. Chemistry benzotiazol Huisgen cycloaddition microwave-assisted synthesis 1 2 3-1H-triazoles nitro-supstituirani benzotiazoli „klik“ reakcija benzotiazol nitro-supstituirani benzotiazoli mehanokemijska sinteza 1 2 3-1H-triazoli Huisgenova cikloadicija „klik“ reakcija sinteza potpomognuta mikrovalovima sinteza potpomognuta mikrovalovima |
| Popis: | U sklopu završnog rada provedena je mehanokemijska sinteza O-alkiliranih 6-nitro-supstituiranih derivata benzotiazola 5a‒10a, 5b‒10b, 5c‒10c, kao i sinteza potpomognuta mikrovalovima benzotiazolnih derivata supstituiranih 1,2,3-1H-triazolom 11a–11c. Ključni prekursori 4-(6-nitrobenzotiazol-2-il)fenola 4a–4c pripravljeni su u glicerolu reakcijom bis(2-amino-5-nitrofenil)disulfida 3 i odgovarajućeg supstituiranog 4-hidroksibenzaldehida. Sinteza ciljanih O-alkiliranih 6-nitro-supstituiranih benzotiazola (5a‒10a, 5b‒10b, 5c‒10c) provedena je iz odgovarajućih fenolnih derivata (4a–4c) u reakciji s određenim alkil-halogenidom u kugličnom mlinu. Sinteza 1,2,3-1H-triazolnih derivata benzotiazola 11a–11c provedena je Cu(I) kataliziranom regioselektivnom 1,3-dipolarnom cikloadicijom iz odgovarajućih terminalnih alkina benzotiazola 5a–5c i trimetilsililazida. Navedenim „klik“ reakcijama koje su provedene u mikrovalnom reaktoru nisu izolirani ciljani produkti. Strukturna i spektroskopska karakterizacija novopriređenih spojeva provedena je 1H i 13C NMR spektroskopijom. As part of this paper, mechanochemical synthesis of O-alkylated 6-nitro-substituted benzothiazole derivatives 5a‒10a, 5b‒10b, 5c‒10c was performed, as well as microwave-assisted synthesis of benzothiazole derivatives substituted with 1,2,3-1H-triazole 11a–11c. Key intermediates 4-(6-nitrobenzothiazol-2-yl)phenols 4a–4c were prepared in glycerol by reaction of bis (2-amino-5-nitrophenyl)disulfide 3 and the corresponding substituted 4-hydroxybenzaldehyde. The synthesis of targeted O-alkylated 6-nitro-substituted benzothiazoles (5a‒10a, 5b‒10b, 5c‒10c) was performed from the corresponding phenolic derivatives (4a–4c) and alkyl halides in a ball mill. The synthesis of 1,2,3-1H-triazole derivatives of benzothiazole 11a–11c was performed by regioselective Cu(I) catalyzed 1,3-dipolar cycloaddition from the corresponding terminal alkynes of benzothiazole 5a–5c and trimethylsilylazide. These "click" reactions performed in the microwave reactor did not yield the target products. Structural and spectroscopic characterization of the newly prepared compounds was performed by 1H and 13C NMR spectroscopy. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|