کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
5264887 1385270 2012 4 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Formation of N-substituted 4- and 7-oxo-4,5,6,7-tetrahydroindoles revisited: a mechanistic interpretation and conversion into 4- and 7-oxoindoles
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Formation of N-substituted 4- and 7-oxo-4,5,6,7-tetrahydroindoles revisited: a mechanistic interpretation and conversion into 4- and 7-oxoindoles
چکیده انگلیسی
An efficient method for the preparation of 4-oxo-4,5,6,7-tetrahydroindoles was successfully applied to the synthesis of N-substituted 7-oxo-4,5,6,7-tetrahydroindoles for the first time. Both isomers where converted into their corresponding 4- and 7-oxoindoles in good yields utilizing a novel aromatization protocol. Based on the impurity profile obtained, however, different mechanisms for the formation of the 4- and 7-oxo-4,5,6,7-tetrahydroindole derivatives are discussed. In addition, the reaction sequences appear to be stereospecific allowing for the direct introduction of a chiral center α to the nitrogen and preparation of enantiomerically enriched products.
ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron Letters - Volume 53, Issue 33, 15 August 2012, Pages 4276-4279
نویسندگان
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