Intramolecular Schmidt reaction of tert-butyl 3-(3-azidopropyl)-4-oxopiperidine-1-carboxylate as a synthetic route to saturated fused aza heterocycles |
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Authors: | A I Moskalenko V I Boev |
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Institution: | 1. Lipetsk State Pedagogical University, ul. Lenina 42, Lipetsk, 398020, Russia 2. Timiryazev Russian State Agrarian University, Timiryazevskaya ul. 49, Moscow, 127550, Russia
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Abstract: | Treatment of the title compound with trifluoroacetic acid induced intramolecular Schmidt reaction with formation of a saturated fused heterocyclic system, tert-butyl 5-oxo-2,3,4,5,7,8,9,9a-octahydro-1H-pyrrolo1,2-a]1,4]-diazepine-2-carboxylate. The latter was reduced with lithium tetrahydridoaluminate, and subsequent treatment with hydrogen chloride in dioxane gave 2,3,4,5,7,8,9,9a-octahydro-1H-pyrrolo1,2-a]1,4]-diazepine dihydrochloride which is a promising intermediate product for the synthesis of N-substituted diazepines with a fused pyrrole ring. |
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