New cyclic zwitterionic building blocks for the synthesis of piperidine-2,4-dione and pyridine-2-one compounds

The Stabilizing Role of the Intramolecular C–H···O Hydrogen Bond in Cyclic Amides Derived From α-Methylbenzylamine

“…Compound 11 was prepared following the methodology previously reported. 32 (R)-5-(Dimethylsulfonio)-2-methyl-6-oxo-1-((S)-1-phenylethyl)-1,2,3,6-tetrahydropyridin-4-olate. To a stirred room temperature solution of the corresponding sulfonium salt (0.55 g, 1.36 mmol) in CH 3 CN (28 mL) was added KOH (0.155g, 2.7 mmol).…”

(7aS)-(–)-Dimethyl(1-oxido-3-oxo-5,6,7,7a-tetrahydro-3H-pyrrolizin-2-yl)sulfonium

“…For background to the synthesis of chiral non-racemic zwitterionic compounds, see: Zang et al (2008); Kappe et al (1983); Palillero et al (2009). For the biological activity of related structures, see: Basco et al (1994); Koruznjak et al (2003).…”

“…Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999 The synthesis of chiral non racemic zwitterionic compounds is an original area of interest in organic chemistry (Zang et al, 2008;Kappe et al, 1983) because they are useful intermediates for the synthesis of diverse interesting nitrogen heterocyclic compounds (Palillero et al, 2009) with interesting biological properties (Basco et al, 1994;Koruznjak et al, 2003).…”

(R)-(+)-Dimethyl[4-oxido-2-oxo-1-(1-phenylethyl)-1,2,5,6-tetrahydropyridin-3-yl]sulfonium

“…Special thanks go to Dr Marcos Flores (USAI-FQ-UNAM) for useful comments. The synthesis of chiral non racemic zwitterionic 4-alkoxy-3-sulfonium ylide pyridine-2-ones is an original area of interest in organic chemistry (Zang et al, 2008;Kappe et al, 1983) because they are useful for the synthesis of piperidine-2,4dione and pyridine-2-one (Palillero et al, 2009) compounds and because of their interesting biological properties (Basco et al, 1994;Koruzňjak et al, 2003).…”