ω-Aminodithioester derivatives were obtained from thionolactams by reaction with an alkyl triflate followed by thiolysis with hydrogen sulfide. The presence of an electron-withdrawing group was required on the N1 position (p-nitrophenyl or benzoyl) to favor the ring opening of γ-, δ- and ε-thionolactams. In the case of β-thionolactam, activation was provided by a CF2 motif in C3 position. Georg Thieme Verlag Stuttgart.
SYNTHESIS, STRUCTURE, AND CHEMICAL PROPERTIES OF TRIMETHYLSILYL DERIVATIVES OF THIOLACTAMS
Trimethylsilyl derivatives of five-, six-, and seven-membered thiolactams with an N-silyl structure were synthesized for the first time.Their alkylation with primary alkyl halides under comparatively mild conditions occurs at the sulfur atom; the reaction with secondary alkyl halides is accompanied by hydrogen halide elimination, and this becomes the only reaction pathway with tertiary halides.The preparative acylation of N-trimethylsilylthiolactams yields N-acyl derivatives; the intermediate formation of S-acylation products was established by means of low-temperature NMR monitoring.
Sergeev, V. N.,Artamkin, S. A.,Pestunovich, S. V.,Albanov, A. I.,Voronkov, M. G.,Baukov, Yu. I.
p. 1490 - 1497
(2007/10/02)
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