The synthesis of the tetracyclic molecule 2-(9,10-dihydro-9,10-propano-anthracen-9-yl)-N-methylethanamine (2) as a homologue of the antidepressant 1-(9,10-dihydro-9,10-ethanoanthracen-9-yl)-N-methylmethaneamine (1) was described. The key intermediate 9-(prop-2-en-1-yl)-9,10-dihydro-9,10-propanoanthracen-12-one (7) was successfully synthesized via a [4+2] cycloaddition of α-bromoacrolein and 9-allyl-anthracene, followed by ring expansion and samarium diiodide deoxygenation.
Tetracyclic bishomobenzoctamine as a homologue of benzoctamine 1 was synthesised. The key intermediate 9-(prop-2-en-1-yl)-9,10-dihydro-9,10-propanoanthracen-12-one was successfully synthesised via [3+4] cycloaddition of tetrabromoacetone on 9-allylanthracene by using ultrasonication at 15-20 °C followed by debromination.
Synthesis of Bishomobenzoctamine 2-(9,10-Dihydro-9,10-propanoanthracen-9-yl)-N-methylethanamine (IX) -[via an ultrasound-assisted [3 + 4] cycloaddition of allylanthracene (III) with tetrabromoacetone]. -(KARAMA*, U.; AL-SAIDEY, A.; ALMANSOUR, A. R.; J.
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