Synthesis and stereochemistry of new trihydrodiazabicyclo-[3.m.n]alkano[4′,5′:1,2]pyrido[3,4-b]indole ring system |
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Authors: | Stanislaw Misztal Maria H Paluchowska Maria J Mokrosz Piotr Bartyzel Jerzy L Mokrosz |
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Abstract: | The classical Pictet-Spengler reaction of tryptamine with the isomeric N-benzylpiperidones 3a, 3b and N-benzylpyrrolidone 3c yielded the spiro derivatives of 1,2,3,4-tetrahydro-β-carboline 5a, 5b and 5c . Cyclocon-densation of the spirotetrahydrocarboline with chloroacetic chloride and the subsequent reductive debenzylation afforded the new ring systems of trihydrodiazabicyclo3.m.n]alkano4′,5′:1,2]pyrido3,4-b]indoles 8a , 8b , and 8c . The structures of the bicyclic systems 8a, 8b , and 8c were determined by using both, high-resolution 1H and 13C nmr techniques and force field and MNDO calculations. |
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