2019
DOI: 10.1021/acs.joc.9b00871
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Regioselective Synthesis of 1-Sulfanyl- and 1-Selanylindolizines

Abstract: We describe herein a new approach to prepare unprecedented bioactive indolizine motifs decorated with organosulfur and organoselenium groups. A total of 12 1sulfanylindolizines and 2 1-selanylindolizines were prepared in excellent yields by an intramolecular annulation of easily prepared chalcogen-containing pyridinium salts. The reaction is fast (1 h at 70 °C or 5 min under sonication) and transitionmetal-free, using glycerol as a green solvent.

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Cited by 20 publications
(12 citation statements)
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“…A Pd (II) /Cu (II) ‐catalyzed sulfanylation was recently developed by Sakai and co‐workers and used in the synthesis of two examples of 1,3‐bis‐sulfanylindolizines 4 . More recently, we have developed the first general methodology to access 1‐sulfanylindolizines selectively, by a base‐promoted intramolecular cyclization of chalcogen‐containing pyridinium salts …”
Section: Introductionmentioning
confidence: 99%
“…A Pd (II) /Cu (II) ‐catalyzed sulfanylation was recently developed by Sakai and co‐workers and used in the synthesis of two examples of 1,3‐bis‐sulfanylindolizines 4 . More recently, we have developed the first general methodology to access 1‐sulfanylindolizines selectively, by a base‐promoted intramolecular cyclization of chalcogen‐containing pyridinium salts …”
Section: Introductionmentioning
confidence: 99%
“…[8] In this context, sulfur-containing indolizines, like the 3-sulfanylindolizine derivative B, is a potent anti-inflammatory, acting as an antagonist of CRTH2 receptor, [9] while the 1-selanylindolizine derivative C showed to be a promising compound for the treatment of oxidative-stressrelated diseases (Figure 1). [10] Despite the pharmacological potential of chalcogenylindolizines, the number of general methods to access these compounds remains scarce. For instance, Cao and co-workers [11] reported in 2018 a peroxide-mediated synthesis of 3-sulfanylindolizines under thermal conditions, in which 1,3-bis(sulfanyl) indolizines could be accessed in the presence of catalytic KI (Scheme 1, #1).…”
Section: Introductionmentioning
confidence: 99%
“…[15] Under sonication, the cavitation effect causes a turbulent flow of liquid phase, which is responsible by enhancing the mass transfer, thus accelerating chemical reactions. [16] This unique property of US-promoted reactions have been explored by us [10,17] and others [18] in the development of green protocols to access efficiently a large and diversified library of chalcogen-containing compounds.…”
Section: Introductionmentioning
confidence: 99%
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