Synthesis of 2‑Aryl-3-(organoselanyl)‑4H‑benzo[4,5]imidazo[2,1‑b][1,3]thiazines Promoted by N‑Fluorobenzenesulfonimide (NFSI)
Ricardo H. Bartz, Pedro S. Souza, Leonardo Rocha, Raquel G. Jacob, Eder J. Lenardão, Márcio S. Silva, Gelson Perin
TL;DR
This paper presents a new method to synthesize selenium-containing benzoimidazothiazine compounds using a safe and efficient oxidizing agent.
Contribution
A novel electrophilic cyclization strategy using NFSI to synthesize selenium-functionalized heterocycles with high yields.
Findings
16 new selenium-functionalized benzoimidazothiazines were synthesized with yields up to 95%.
NMR experiments helped identify reaction intermediates and clarify the mechanism.
The method uses a broad range of substrates and a nonhazardous oxidizing agent.
Abstract
An approach has been developed for the direct synthesis of various selenium-functionalized benzo[4,5]imidazo[2,1-b][1,3]thiazine derivatives via the electrophilic cyclization reaction between 2-(methylthio)-1-(3-arylprop-2-yn-1-yl)-1H-benzo[d]imidazoles and diorganyl diselenides promoted by N-fluorobenzenesulfonimide (NFSI). This strategy is used to construct fused heterocyclic scaffolds based on selenium-functionalized 4H-benzo[4,5]imidazo[2,1-b][1,3]thiazines using NFSI as a stable and nonhazardous oxidizing agent in the presence of CH3CN at 80 °C. The protocol allowed a broad substrate scope leading to the synthesis of 16 novel selenium-functionalized benzo[4,5]imidazo[2,1-b][1,3]thiazines in yields of up to 95%. Furthermore, control studies, including 1H, 19F, and 77Se NMR experiments, were conducted to identify intermediates, which contributed to the elucidation of…
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Taxonomy
TopicsSynthesis and Reactivity of Sulfur-Containing Compounds · Organoselenium and organotellurium chemistry · Phenothiazines and Benzothiazines Synthesis and Activities