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Intramolecular nucleophilic substitution of chlorine in 2-chloro-3-(alkanesulfonylamino)pyridines furnishes N-alkyl-1,3-dihydroisothiazolo[4,3-b]pyridine 2,2-dioxides (pyridosultams,8 ), which undergo thermal extrusion of SO 2 giving heteroanalogues of aza-ortho-xylylenes 9. These reactive 1-azadienes enter [4+2] cycloaddition with dienophiles leading to tetrahydro[1,5]naphthyridines 11....
Nitro derivatives of 2,1-benzisothiazoline 2,2-dioxide (benzosultams) undergo thermal elimination of sulfur dioxide yielding very reactive, non-isolable aza-ortho-xylylenes. It was found that this reaction can be performed in the injector of the gas chromatograph at 300 - 350°C and the formed aza-ortho-xylylenes can be trapped by appropriate reagents added to the injected solution. In the preliminary...
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