کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
5225597 1383552 2008 7 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Improved preparation of alkyl 2-(3-indolyl)-3-nitroalkanoates under fully heterogeneous conditions: stereoselective synthesis of alkyl (E)-2-(3-indolyl)-2-alkenoates
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Improved preparation of alkyl 2-(3-indolyl)-3-nitroalkanoates under fully heterogeneous conditions: stereoselective synthesis of alkyl (E)-2-(3-indolyl)-2-alkenoates
چکیده انگلیسی

Ethyl 3-nitro-2-alkenoates can be generated starting from nitroalkanes and ethyl 2-oxoacetate under heterogeneous conditions that minimize work-up procedures, avoid any purification step and direct manipulation of the nitroalkene system. Reaction of ethyl 3-nitro-2-alkenoates, formed in situ from their acetoxy precursors, with indoles in the presence of basic alumina affords ethyl 2-(3-indolyl)-3-nitroalkanoates that are central intermediates for the preparation of tryptamines and carboline alkaloids. A base promoted elimination of nitrous acid from these nitroindolyl derivatives readily produces ethyl 2-(3-indolyl)-2-alkenoates with high E stereoselectivity. The latter compounds can be used as Michael acceptors in intra- and intermolecular reactions with nucleophilic reagents.

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron - Volume 64, Issue 23, 2 June 2008, Pages 5435-5441
نویسندگان
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