Synthesis and conformational study of 1,2,3,4,5,6,7,8-octahydro-1,6-naphthiridines |
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Authors: | T V Esipova A A Borisenko P B Terent’ev G V Grishina R Herzshuh |
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Institution: | (1) Lomonosov Moscow State University, Moscow, 119992, Russia;(2) Leipzig University, BRD |
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Abstract: | A new class of endocyclic enamines, 1,6-disubstituted 1,2,3,4,5,6,7,8-octahydro-1,6-naphthiridines, was synthesized from 4-piperidone imines by successive subjecting the latter to lithiation with lithium diethylamide, to alkylation with 1-bromo-3-chloropropane, and to intramolecular cyclization. All stages were carried out as a unique process without isolation of the intermediate compounds. A thorough optimization of the process conditions, workup, and product storage was carried out. The conformational study of 1,6-disubstituted 1,2,3,4,5,6,7,8-octahydro-1,6-naphthiridines was performed. |
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