کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
5216258 1383257 2014 15 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Conjugate addition nitro-Mannich reaction of carbon and heteroatom nucleophiles to nitroalkenes
ترجمه فارسی عنوان
واکنش کربن و نوکلئوفیل های نیتروآمنکیک به نیترو آلکین ها
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
چکیده انگلیسی

The conjugate addition nitro-Mannich reactions of ethyl-β-nitroacrylate (1) and β-nitrostyrene (2) with electron rich aromatic nucleophiles, stabilized carbanions, alcohols, amines, thiols, and diphenyl phosphine oxide were investigated. The one pot conjugate addition nitro-Mannich reaction was unsuccessful except for the addition of alkoxides to 2 in alcohol as solvent. Isolation of the conjugate addition products followed by deprotonation with nBuLi and treatment with a simple imine in the presence of TFA led to β-nitroamine derived products. Products derived from 1 spontaneously cyclised in only a few examples and on the whole led to inherently unstable products. Products derived from 2 were isolated as their trifluoroacetamides, gave good yields of single diastereoisomers for aromatic and alkoxide nucleophiles and the structures were verified by single crystal X-ray crystallography. Products derived from amine nucleophiles were isolated in low yields while sulfur nucleophiles gave poor diastereoselectivities.

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ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron - Volume 70, Issue 49, 9 December 2014, Pages 9337–9351