کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
5289267 1385853 2006 4 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Aromaticity in azlactone anions and its significance for the Erlenmeyer synthesis
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Aromaticity in azlactone anions and its significance for the Erlenmeyer synthesis
چکیده انگلیسی
Azlactone anions-the key intermediates in the classical Erlenmeyer synthesis of amino acids-apparently possess aromatic stabilization, as indicated by the relative rate of base catalyzed deuterium exchange in the following analogs: 1-methyl-2-phenyl-5(4H)-imidazolone > 2-phenyl-5(4H)-oxazolone (azlactone) > 3,3-dimethyl-2-phenyl-4(3H)-pyrrolone. This is paralleled by the relative rate of condensation of these compounds with hexadeuteroacetone. Reported pKa data also suggest that the azlactone products of the Erlenmeyer synthesis are analogs of the fulvenes.
ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron Letters - Volume 47, Issue 32, 7 August 2006, Pages 5763-5766
نویسندگان
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