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A new way to the synthesis of tricyclic compounds via nitrone 1,3-cycloaddition dipolar reaction.

OBJECTIVE This work is dealing with the development of new methodologies in the field of 1,3-dipolar Cycloaddition. METHOD A new series of tricyclic derivatives (13a-d), were synthesized via 1, 3-dipolar… Click to show full abstract

OBJECTIVE This work is dealing with the development of new methodologies in the field of 1,3-dipolar Cycloaddition. METHOD A new series of tricyclic derivatives (13a-d), were synthesized via 1, 3-dipolar cycloaddition of nitrones (8a-c) and (9a-c), using intramolecular cyclisation at reflux of toluene and radical intramolecular cyclisation in the presence of tributyltin hydride and AIBN as an initiator in benzene which are two techniques to prepare cycloadducts (11a-d), followed by cleavage of the N-O bond was thus performed using SmI in THF. RESULT The structures of these new tricyclic derivatives have been confirmed by Mass, 1H-NMR (1d, 2d), 13C-NMR and IR spectral data. CONCLUSION In summary, we have investigated the possibility of synthesizing some new and straight forward access to an A-C-D tricyclic skeleton of morphinans from symmetrical arylcyclohexadienes, methodology that can give access to different classes of alkaloids.

Keywords: synthesis tricyclic; synthesis; way synthesis; tricyclic compounds; new way; cycloaddition

Journal Title: Current organic synthesis
Year Published: 2022

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