Synthese von neuen 1,2,6‐Thiadiazinen und 1,3,2,4‐Dithiadiazinen

Abstract

Synthesis of New 1,2,6-Thiadiazines and 1,3,2,4-DithiadiazinesThe synthesis of some new benzo-and benzothieno-substituted 1,2,6-thiadiazin-3-0nes 4a -c, 9 a -f by cyclisation of dialkylsulfur diimides l a -c with halide substituted acid chlorides 2 and 5 a -c is described. Analogous cyclisation of the sulfonyl chloride 6 with l a -d leads to 1,3,2,4-dithiadiazines 10a -d. In analoger Weise reagieren 1 a -c mit nitrosubstituierten o-Chlorbenzoylchloriden 5a -c zu den leuchtend gelben 2,1,3-Benzothiadiazinen 9a -f. ErwartungsgemaB erfolgt im Falle 7f bei der Cyclisierung unter basisch-methanolischen Bedingungen eine gleichzeitige Substitution der 4-Position zu 9 f .

Sulfondiimines: synthesis, derivatisation and application

“…46 Ried reacted N,N 0 -unsubstituted sulfondiimines 5a with acylchlorides 74 or sulfonylchlorides 77 (Scheme 28). 47 Thereby, bicyclic and tricyclic (di)thiadiazines 76 and 79 were obtained by ring closure of acyclic intermediates 75 and 78.…”

“…1 As a result, replacements of these moieties have become powerful tools for Scheme 28 Condensations of N,N 0 -unsubstituted sulfondiimines 5a with acylchlorides 74 or sulfonylchlorides 77 to give thiadiazines 76 or dithiatriazines 79, respectively. 47 Scheme 29 Three-step protocol for the synthesis of 1,2,4-thiadiazines 83 with one exocyclic nitrogen substituent starting from N,N 0 -unprotected S,S-dialkyl-sulfondiimines 5a and N-cyanoimidates 80. 4 Scheme 30 One-pot protocol for the synthesis of 1,2-thiazines 86 with one exocyclic nitrogen substitutent starting from S-methyl S-arylsulfondiimines 84 and propargylketones 85.…”