Thioacrylamides

The dihydrothiopyran unit has been fused onto [60]fullerene through reaction with a thioacrylamide and an acyl chloride (95CC565). Cycloadditions also feature in the synthesis of... 

Acyclic alkenic sulfur compounds have also been obtained via pyrolytic rDA reactions. A general route to thioacrylamides utilizing rDA reactions under FVP conditions has been developed. The rDA reaction of the appropriate adducts yields thioacrylamide, V-methylthioacrylamide and NA -dimethyl-thioacrylamide in approximately quantitative yield (equation 13). The high reactivity of these a,3-unsaturated thioamides had previously limited their availability. a,3-Unsaturated acyclic chio-ketones such as (17) were prepared via a rDA reaction using a FVP technique. These highly reactive species dimerize to 4//-l,3-dithiins (18) on warming to-60 °C (equation 14). ... 

Among miscellaneous recent papers concerned with the reactivity of thiono- and dithio-acids and -esters [including those reporting the synthesis of 1,3-thiazine derivatives from 2-iminocyclopentanedithiocarboxylic acid, the use of chlorothionoformates for the conversion of aldoximes into nitriles, and the rapid, exothermic reaction of ethyl dithiopropionate with t-butoxy-bis(dimethylamino)methane, yielding 3-dimethylamino-2,7VA -trimethyl-thioacrylamide (181 = R = R = Me) ] is a... 

Acyl-A -dihydrothiopyrans, e.g. (33), have been obtained by Diels-Alder reactions and Cope rearrangements of intermediate 2-thioacyl-A -dihydropyrans. Certain 3-aryl-2-cyanO thioacrylamides, such as (34), dimerize in a (4, + 2,) mode to give a A -dihydrothiopyran, e.g. (35). ... 

Extrapolating the vinylogous amide theme, 2-amino-5-acylthiophenes can be prepared from 3-amino-thioacrylamides, with the formation of the 4,5-bond in the ring closing step [114—117]. Thus, 3-amino-thioacrylamides 45 are S-alkylated... 

In a related work, it was found preferable to protect (Ac or Boc) the nitrogen of the 3-amino-thioacrylamide before reaction with the 2-halo-carbonyl component ... 

Scheme 71 The synthesis of a 2-amino-5-acylthiophenes frran 3-amino-thioacrylamides [116]...

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