Synthesis of highly substituted tetrahydroquinolines using ethyl cyanoacetate via aza-Michael–Michael addition
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چکیده
منابع مشابه
Enantioselective synthesis of 3-substituted 1,2-oxazinanes via organocatalytic intramolecular aza-Michael addition.
A highly enantioselective intramolecular 6-exo-trig aza-Michael addition was developed to afford chiral 3-substituted 1,2-oxazinanes in high yields (up to 99% yield) and good enantioselectivities (up to 98/2 er). These reactions were enabled by a quinine-derived primary-tertiary diamine as a catalyst and pentafluoropropionic acid (PFP) as a co-catalyst.
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An optically active tetrahydroquinoline intermediate (5) was prepared in 8 steps from monoprotected ethylene glycol, using a Pd-catalysed aza-Michael reaction to induce chirality. This can be transformed into three Galipea alkaloids (angustureine, galipeine and cuspareine). The proximity of a benzyloxy group is found to exert profound effects in several steps of the synthesis.
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A new efficient method for the synthesis of carboacyclic nucleosides as biologically interesting compounds via aza-conjugate addition of pyrimidine nucleobases to a,β-unsaturated esters in the presence of catalytic amount of LiOH.H2O (1.2-4.8 mol%) under microwave irradiation is described. This method affords the title compounds in good to excellent yields and i...
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15 صفحه اولan efficient protocol for the synthesis of carboacyclic nucleosides via aza-conjugate addition reaction
a new efficient method for the synthesis of carboacyclic nucleosides as biologically interesting compounds via aza-conjugate addition of pyrimidine nucleobases to a,β-unsaturated esters in the presence of catalytic amount of lioh.h2o (1.2-4.8 mol%) under microwave irradiation is described. this method affords the title compounds in good to excellent yields and in short reaction times.
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ژورنال
عنوان ژورنال: RSC Advances
سال: 2020
ISSN: 2046-2069
DOI: 10.1039/d0ra01264e