Formation of Two Bonds Atom Fragment by Other Processes

4 Formation of Two Bonds [3+2] Atom Fragment by Other Processes 

The double Herz condensation of ALmethyl-2,6-diaminopyridinium triflate 155 and its 4-substituted derivatives with S2CI2 at reflux in MeCN gives in moderate yields the appropriate bis[l,2,3]dithiazolopyridinium triflates 16d, 17a, and 17b (Equation 39) 2002CC2562, 2004CM1564 . For R = H and R=Me, reaction times and reaction temperature must be minimized to prevent chlorination. 

2-Aminocyclopent-l-ene- and 2-aminocyclohept-l-enecarbonitriles react with a mixture of S2Cl2, SCl2, and Bu 3N to give chlorinated derivatives of cyclopenta- 44 and cyclohepta- 45 dithiazoles (Equations 40 and 41) 2005EJ05055 . 

3-Benzodithiazol-6-ones 156 are prepared from/ -benzoquinone-4-oximes, S2C12, IV-ethyldiisopropylamine, and iV-chlorosuccinimide (NCS Equation 42) 1998T223 . Some ring chlorination occurs, but 2,6-substituents are retained in the products except for a tert-butyl group, which is replaced by chlorine. 

4-Naphthoquinone 4-oxime and 1,2-naphthoquinone 2-oxime similarly give the dithiazole derivatives 39 and 40 1998T223 . 

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