Synthesis of functionalized tetrahydro-1, 3-diazepin-2-ones and 1-carbamoyl-1 H-pyrroles via ring expansion and ring expansion/ring contraction of …

AA Fesenko, LA Trafimova, AD Shutalev

Index: Fesenko, Anastasia A.; Trafimova, Ludmila A.; Shutalev, Anatoly D. Organic and Biomolecular Chemistry, 2012 , vol. 10, # 2 p. 447 - 462

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Citation Number: 20

Abstract

A general approach to 6-phenylthio-substituted 2, 3, 4, 5-tetrahydro-1H-1, 3-diazepin-2-ones based on the ring expansion reaction of 1, 2, 3, 4-tetrahydropyrimidin-2-ones under the action of nucleophiles has been developed. The first step of the synthesis was preparation of N-[(2-benzoyloxy-1-tosyl) ethyl] urea by three-component condensation of 2- benzoyloxyethanal, urea and p-toluenesulfinic acid. Nucleophilic substitution of the tosyl ...