FOURIER-TRANSFORM RAMAN AND INFRARED SPECTRA AND VIBRATIONAL ASSIGNMENT FOR SOLID GLUTARIMIDE

Abstract

The FT-Raman and FT-IR spectra of crystalline glutarimide and its N-deuterated derivative have been recorded in the range 4000-100 cm^?1. A complete vibrational assignment is given for all internal modes and is supported by normal coordinate analysis based on a general valence force field. The calculated frequencies are in very good agreement with experiment. A close similarity is found for frequencies of the corresponding vibrations of glutarimide and uracils in the solid state. It is concluded that the strength of hydrogen bonding in glutarimide is very similar to that in crystalline pyrimidine nucleic bases.     

1,8‐Diazabicyclo[5.4.0]undec‐7‐ene: A Remarkable Base in the Debromination of 4‐ or 5‐Substituted N‐Benzyl α‐Bromo‐α‐p‐Toluenesulfonylglutarimide

Debromination of N‐benzyl 4‐ or 5‐substituted α‐bromo‐α‐p‐toluenesulfonylglutarimides is achieved with 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU) to give the N‐benzyl 4‐ or 5‐substituted α‐p‐toluenesulfonylglutarimides. The DBU/THF system is applied to a new methodology for the synthesis of bicyclic glutarimide skeleton in moderate yields.     

Synthetic Study of 4‐Substituted Piperidine Ring in Elarofiban,RWJ‐50042, Tirofiban and Paroxetine

A new strategy for synthesizing a 4‐substituted piperidine ring uses the formal [3+3] cycloaddition reaction as the key protocol. This method provides a convenient formal synthesis of elarofiban, RWJ‐50042, tirofiban and paroxetine.     

Different solution and solid-state conformations of the antibiotic cycloheximide

The ¹H NMR spectra of the antibiotic cycloheximide in CDCl₃ and CD₃OD have been assigned. Analyses of coupling constants and difference NOE spectra showed different conformations in these two solvents, due to changeover between intra- and inter-molecular hydrogen bonding. The twist boat cyclohexanone found in the solid state was not detected in solution. The results are compared with the solution and solid-state conformations of the antitumour agent sesbanimide A.     

An isocyanide-based three-component reaction: synthesis of fully substituted N-alkyl-2-triphenylphosphoranylidene glutarimides

A three-component condensation reaction between an isocyanide, an electron-deficient acetylenic ester and (ethoxycarbonylmethyl)triphenylphosphonium bromide efficiently provides fully substituted N-alkyl-2-triphenylphosphoranylidene glutarimides in a one-pot reaction without any activation or modification.