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Synthesis of indolizines from pyridinium 1,4-zwitterionic thiolates and α-functionalized bromoalkanes via a stepwise [(5+1)−1] pathway

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Abstract

The synthesis of pyridothiazines was achieved using pyridinium 1,4-zwitterionic thiolates and α-functionalized bromoalkanes via a formal [5+1] pathway. Further studies demonstrated that the synthesis of indolizines could be accomplished via a stepwise [(5+1)−1] pathway with unstable pyridothiazines as the transient intermediates from the same starting materials. The net transformation involves a sequence of annulation, oxidation and ring-contraction/desulfuration.

Graphical abstract: Synthesis of indolizines from pyridinium 1,4-zwitterionic thiolates and α-functionalized bromoalkanes via a stepwise [(5+1)−1] pathway

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Article information


Submitted
14 May 2020
Accepted
12 Jun 2020
First published
12 Jun 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Synthesis of indolizines from pyridinium 1,4-zwitterionic thiolates and α-functionalized bromoalkanes via a stepwise [(5+1)−1] pathway

B. Cheng, X. Zhang, Y. Li, H. Li, Y. He, Y. Li, T. Wang and H. Zhai, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC03446K

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