Synthesis of N,N-Disubstituted Lactone Hydrazones via (Sulfonylimino)-ethers

Article abstract of DOI:10.1002/hlca.19910740837

The dihydropyran 3 reacts with sulfonyl azides to give the known (sulfonylimino)-ethers (=lactone sulfonylimines) 4 and 18.Reaction of 4 with NH2NH2*H2O leads to the aminotriazole-dibutanol 5, characterized as its tetraacetate 8, and not, as previously claimed, to 6 or 7.Similarly, the dihydrofuran-derived (tosylimino)-ether 10 yields structure 11.The structure of 5 was established by X-ray analysis, and a mechanism for its formation is proposed.Reaction of 4 with NH2NMe2 afforded the lactone hydrazone 16 and the hydrazidine 17.Catalysis by imidazole suppressed the formation of 17.Similarly, the <(trifluoromethyl)sulfonyl>imine 18 yielded 16, and, by reaction with NH2N(Me)Ph or 4-amino-4H-1,2,4-triazole, the lactone hydrazone 19 and the adduct 20, respectively.The 1,4-lactone hydrazone 21 was obtained from 10 or from 22.The structure of 20 was established by X-ray analysis.Treatment of 16 with BuLi followed by BnBr yielded the α-alkylated lactone hydrazone.