Sugar thioamides

Fig. 5. Spectral parameter relationships for (Z) and (E) rotamers of sugar thioamides.

The preparation and reactions of V-thiocarbonyl carbohydrate derivatives, such as sugar isothiocyanates, thioamides, thioureas, thiocarbamates and their conjugates have been the subject of valuable comprehensive as well as specialized accounts, which should be consulted for details.198... 

Chapter 19 - The results of experimental researches on the synthesis of sugars derivatives with glycosylamide and thioamide bonds have been presented in this work. The possibility of using their in the preparative chemistry of sugars, some fields of medicine and agriculture has been shown. 

Thioamides can serve as surrogates for isothiocyanates in the Marckwald synthesis. For example, reaction of a-amino acetals 1278 with thioamides 1277 in the presence of HgClz affords amidine intermediates, which cyclize to form imidazoles under acidic conditions. This method has been applied to synthesize a variety of sugar imidazoles (Scheme 324) <2005HCA10, 2004HCA3035, 2004HCA719, 2000TA435>. 

Pyrazinethionhydroxamic acid amide Aminothiazoles Aminothiophenes Aminopyrazoles Aminoisoxazoles Pyrroloazepinones Aminotriazolopyrimidines Aminotetrahydronaphthyridines Aminopyrazolopyridines Aminopyridazinones Aminopyndopyrimidines Amino- 1,3,4-thiadiazoles Aminoimidazoles Sulfonamides Amino sugars N-Aiylbenzamidines Thioamides Benzylamines Aromatic acid amides... 

CHEMISTRY AND DEVELOPMENTS OF jV-THIOCARBONYL CARBOHYDRATE DERIVATIVES SUGAR ISOTHIOCYANATES, THIOAMIDES, THIOUREAS, THIOCARBAMATES, AND THEIR CONJUGATES... 

Starting from 5-gluconolactone the sugar-derived thioamide (81) can be obtained via thionation of the corresponding amide with LR. The related thiolactam (82) was prepared from the lactam because a higher yield of the desired oxime could be achieved with (82). ... 

---