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Synthesis and Properties of 1,3-Diaryl-5,6-dihydro-8H-imidazo[2,1-c]-1,4-oxazinium Bromides
Authors:A M Demchenko  N A Shtil  A P Andrushko  A N Krasovsky  A N Chernega  E B Rusanov  V V Pirozhenko  M O Lozinskii
Institution:(1) T. G. Shevchenko Chernigov Pedagogical University, Chernigov, 14013, Ukraine;(2) Chernigov Technological University, Chernigov, 14027, Ukraine;(3) Ukraine National Academy of Sciences, Institute of Organic Chemistry, Kiev, 02094, Ukraine
Abstract:It has been established that the condensation of 3-(4-methoxyphenylamino)-5,6-dihydro-2H-1,4-oxazine with substituted phenacyl bromides occurs at the exocyclic nitrogen atom with formation of 3-aryl-3-hydroxy-1-(4-methoxyphenyl)-2,5,6,8-tetrahydro-3H-imidazo2,1-c]-1,4-oxazinium bromides. By treatment of the latter with acetic anhydride 3-aryl-1-(4-methoxyphenyl)-5,6-dihydro-8H-imidazo2,1-c]-1,4-oxazinium bromides are formed. The structures of the compounds synthesized were determined via 1H NMR spectroscopy and X-ray diffraction.
Keywords:heterocyclic amidines  3-(4-methoxyphenylimino)-5  6-dihydro-2H-1  4-oxazine  substituted phenacyl bromides  3-ethoxy-5  6-dihydro-2H-1  4-oxazine  exocyclic nitrogen atom  alkylation
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