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2 Polish Journal of Chemistry

2 1998

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Trapping of thiocarbonyl ylides with NH-azoles; A novel route to N-substituted azoles

Mlostoń G., Gendek T., Heimgartner H.

Polish Journal of Chemistry

1998

Vol. 72, nr 1

66-72

Thermal decomposition of 2,5-dihydro-1,3,4-thiadiazoles (1) in the presence of imidazole, pyrazole, 3-phenylpyrazole, and 1,2,4-triazole, respectively, yielded S,N-acetals of type 4. Interception of initially formed thiocarbonyl ylide 2 by the NH-azole is proposed as the reaction mechanism. Treatment of the S,N-acetals 4 with Raney-Ni gave N-substituted azole 6.

Reversed imidazole nucleosides. Alternative pathway of synthesis

Walczak K., Suwiński J.

Polish Journal of Chemistry

1998

Vol. 72, nr 6

1028-1036

The reversed imidazole nucleosides were obtained on three independent routes: a) by the nucleophilic substitution of terminal tosylate group in sugar derivatives with imidazole-1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) salts, b) from monosugar derivatives with unprotected terminal hydroxy group and substituted imidazoles, under the Mitsunobu reactions conditions, c) by the reaction of monosugars possessing terminal primary amino group with 1,4-dinitroimidazoles. Limitation of these routes are discussed.