Transformation of zwitterionic pyridine derivatives to a spiro fused ring system: azoniabenzo[de]fluorine. Synthesis and mechanistic rationalization

Palkó, Roberta and Egyed, Orsolya and Rokob, Tibor András and Bombicz, Petra and Riedl, Zsuzsanna and Hajós, György (2015) Transformation of zwitterionic pyridine derivatives to a spiro fused ring system: azoniabenzo[de]fluorine. Synthesis and mechanistic rationalization. The Journal of Organic Chemistry, 80 (1). pp. 174-179. ISSN 0022-3263

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Abstract

Reaction of aryl- and benzylsulfanopyridinium amidates bearing a methyl group in position 6 with two equivalents of diphenylketene afforded a spiro fused ring system: azoniabenzo[de]fluorine. By use of excess amount of ketene, a distinct reaction was observed via which a 1H-pyrrolo[3,2- b]pyridin-2(3H)-one derivative was furnished. Structure of the tetracyclic spiro-fused ring system was unambiguously confirmed by X-ray diffraction and its formation was rationalized by DFT calculations.

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