Journal :   Asian Journal of Research in Chemistry

Volume No. :   5

Issue No. :  12

Year :  2012

Pages :   1460-1463

ISSN Print :  0974-4169

ISSN Online :  0974-4150


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Synthesis of [9,10-Dihydro-9-(2-methylaminoethyl)-9,10-propanoanthracene]

Address:   Adel Al-Saeedi1,2, Usama Karama1, Mazahar Farooqui 2*
1Department of Chemistry, College of Science, King Saud University Saudi Arabia.
2Post Graduate and Research Center, Maulana Azad College, Aurangabad (MS).
*Corresponding Author

Reaction of anthrone R1 with Grignard reagent to give 9- substituted anthracene R2 which treatment with a-bromoacroline to give R3. Reaction of R3 with 1M NaOH resulted in transformation into the ring expanded a-hydroxy ketone R4. Transformation of a-hydroxy ketone by using samarium diiodide led to the desired key intermediate ketone R5, which treatment with hydrazine hydrate to afford tetracyclic hydrocarbon R6, which Reaction with BH3 to give alcohol R7. Conversion alcohol into the chloride by using triphenylphosphane in CCl4 to gave R8. Interaction of R8 with methyl amine in methanol afforded Bishomobenzoctamine R9, Scheme 1 as a homologue of the anxiety benzoctamine R.
cycloaddition; anthrone; benzoctamine; homologue; anxiety.
Adel Al-Saeedi, Usama Karama, Mazahar Farooqui. Synthesis of [9,10-Dihydro-9-(2-methylaminoethyl)-9,10-propanoanthracene]. Asian J. Research Chem. 5(12): Dec., 2012; Page 1460-1463.
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