Reactions With Hydrazidoyl Halides Ii [1]: Synthesis and Reactions of 2-Bromothienylglyoxal-2-Phenylhydrazone

2-Bromoacetylthiophene reacted with dimethylsulfide in ethanol to afford dimethylsulfonium bromide 2, which reacted with N-nitrosoacetanilide to give 2-bromo-thienylglyoxal-2-phenylhydrazone (3). 3 reacted with pyridine and with triphenylphosphine to give 4a and 4b, respectively. 3 reacted also with morpholine, sodium thiophenolate or potassium cyanide to afford the corresponding hydrazones 5a–c, respectively. 3 reacted also with potassium thiocyanate and with potassium selenocyanate to give the thiadiazoline 6a and selenadiazoline 6b. 3 is utilized also for the synthesis of several heterocycles via its reactions with malononitrile, benzoylacetonitrile, dibenzoylmethane, ω-benzenesulfonylacetophenone, N-arylmaleimides and benzalaniline. Structural assignments have been made on the basis of elemental analyses, spectral data and independent synthesis wherever possible.