Synthesis of Dopamine, Rotigotin, Ladostigil, Rasagiline Analogues 2-Amino-4,5,6-trimethoxyindane, 1-Amino-5,6,7-trimethoxyindane, and Their Sulfamide Derivatives
| Autor: | Kadir Aksu, Bünyamin Özgeriş, Süleyman Göksu, Ferhan Tümer |
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| Rok vydání: | 2014 |
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| Zdroj: | Synthetic Communications. 45:78-85 |
| ISSN: | 1532-2432 0039-7911 |
| DOI: | 10.1080/00397911.2014.957321 |
| Popis: | Dopamine, rotigotin, ladostigil, and rasagiline analogues 2-amino-4,5,6-trimethoxyindane and 1-amino-5,6,7-trimethoxyindane were synthesized starting from 5,6,7-trimethoxyindan-1-one for the first time with 34% and 45% total yields. α-Carboxylation of indanone, reduction of ketone group with Et3SiH, basic hydrolysis of ester, Curtius reaction of the acid, and addition of BnOH afforded the corresponding carbamate. Pd-C-catalyzed hydrogenolysis of carbamate and deprotonation of amine hydrochloride with NaOH gave the dopamine and rotigotin analogue 2-aminoindane. Reduction of 5,6,7-trimethoxyindan-1-one with NaBH4 afforded the alcohol, which was then converted to the azide derivative via Mitsunobu reaction with diphenylphosphoryl azide; Pd-C catalyzed hydrogenation of the azide to the amine hydrochloride and then deprotonation of the amine hydrochloride with NaOH furnished the ladostigil and rasagiline analogue 1-aminoindane. These amines and BnOH were reacted with CSI to produce sulfamoyl carbamates, which were converted to sulfamides via Pd-C-catalyzed hydrogenolysis reaction with 20% and 25% total yields. |
| Databáze: | OpenAIRE |
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