Figure 3 | Scientific Reports

Figure 3

From: Rational design of novel benzisoxazole derivatives with acetylcholinesterase inhibitory and serotoninergic 5-HT4 receptors activities for the treatment of Alzheimer’s disease

Figure 3The alternative text for this image may have been generated using AI.

Synthesis of C3 substituted-benzisoxazole by a C-C bond. Reagents and conditions: (a) NH2OH.HCl, NaOAc, H2O/EtOH (3:2), 1 h, rt then 2 h, reflux, 90% (mixture of isomers E/Z 2:1) (b) t-BuONa, cat. DMEDA, cat. CuI, dry THF, 1 h, rt, 27% (c) LDA 1.0 M sol., dry THF, −78 °C then tert-butyl 4-(iodomethyl)piperidine-1-carboxylate, 1 h, −78 °C, 22% (d) TFA, CH2Cl2, rt, 1 h (e) bromomethylcyclohexane, K2CO3, DMF, 110 °C, 3 h, 50% (2 steps) (f) bromomethylbenzene, Et3N, CH2Cl2, rt, 15 h, 38% (2 steps) (g) 1-iodo-2-methyl-propane, Et3N, DMF, 110 °C, 3 h, 15% (2 steps).

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