Sheng-Zhen Xu

Iminophosphorane-mediated efficient synthesis of new tricyclic 3,5-dihydro-1,2,3-triazolo[4,5- d ]-1,2,4-triazolo[1,5- a ]pyrimidin-9-ones

The carbodiimides 2, obtained from aza-Wittig reactions of iminophosphorane 1 with aromatic isocyanates, reacted with hydrazine to give selectively 6-amino-7H-1,2,3-triazolo[4,5-d]pyrimidin-7-ones 5. Compounds 5 were further transformed to iminophosphoranes 6 by reaction with triphenylphosphine, hexachloroethane and triethylamine. A tandem aza-Wittig reaction of iminophosphorane 6 with isocyanate or acyl chloride generated previously unreported 3,5-dihydro-1,2,3-triazolo[4,5-d]-1,2,4-triazolo[1,5-a]pyrimidin-9-ones 10 or 12 in satisfactory yield. X-ray structure analysis of 10 g verified the proposed structure and the reaction selectivity.

Organocatalytic synthesis and sterol 14α-demethylase binding interactions of enantioriched 3-(1H-1,2,4-triazol-1-yl)butyl benzoates

1H-1,2,4-Triazole reacted with 2-butenal in the presence of diaryl prolinol silyl ether 3 and benzonic acid to give 3-(1H-1,2,4-triazol-1-yl)butanal 4, which was subsequently reduced and then treated with various acyl chloride to generate enantioriched 3-(1H-1,2,4-triazol-1-yl)butyl benzoates 6. Some of triazoles 6 exhibited strong binding interactions with the cytochrome P450-dependent sterol 14alpha-demethylase (CYP51). For example, compound (R)-6f showed the best binding activity with K(d) 0.3381 microM.

2-Ethoxy-3-phenyl-1-benzothieno[3,2-d]pyrimidin-4(3H)-one

Derivatives of thienopyrimidines are of great importance because of their remarkable biological properties (Walter, 1999a,b). In recent years, we have been engaged in the preparation of heterocyclic derivatives containing a fused pyrimidinone system using the aza-Wittig reaction (Ding et al., 2004). Some X-ray crystal structure reports for thienopyrimidine derivatives have been published (Xu et al., 2005; Cao et al., 2006). Here, the structure of the title compound, (I), which may be used as a new precursor for obtaining bioactive molecules, is reported (Fig. 1).