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Preparation And Derivatization Of Novel Sydnonimines And Their Esters, Timothy Luke Teschler
Preparation And Derivatization Of Novel Sydnonimines And Their Esters, Timothy Luke Teschler
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Some years ago, we reported that 3-phenylsydnone underwent dilithiation to yield the dilithio species, upon treatment with n-butyllithium. Subsequent reactions with electrophiles led to variously substituted aryl sydnones, dependent on the nature of the electrophile employed. Sydnonimines, exocyclic nitrogen analogs of sydnones, exhibit interesting biological properties and, accordingly, it was of value to explore whether or not the dilithiation approach could be extended to such species. In the present work a series of N-6-ethoxycarbonyl-3-arylsydnonimines were synthesized from the corresponding sydnonimine hydrochlorides in moderate yields (22-77%). Attempted dilithiations of N-6-ethoxycarbonyl-3-arylsydnonimines and trapping with iodine proved to be problematic, yielding only the …
Synthetic Routes To A Fused-Ring Sydnoquinazoline, Gregory Edmond Storer
Synthetic Routes To A Fused-Ring Sydnoquinazoline, Gregory Edmond Storer
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In this research, 5-methylsydno-[3,4-a]quinazoline was synthesized via multiple methodologies, the best of which yielded the target compound in 50 % overall yield for the six steps. Synthesis of this compound in reasonable yields and exploration of its chemical behavior is of particular interest as a putative NO-prodrug. As an initial approach to the synthesis and accumulation of the compound of interest, attempts were made to optimize the existing synthetic pathway to its precursors. The starting material, 3-(2-acetylphenyl)sydnone, was prepared in 3 steps from commercially available starting material in good yields. This sydnone compound was then converted to the versatile intermediate, …