By Julio Alvarez-Builla, Juan Jose Vaquero, José Barluenga
The must-have reference within the box of heterocyclic compounds, comprehensively masking their synthesis, constitution and chemical and actual properties.By offering merely the real evidence, this guide succeeds in being entire whereas containing the data in precisely volumes.An updated resource of high quality info for all natural and medicinal chemists operating during this box in and academia.
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Sample text
Loading could be used in the presence of potassium carbonate with only a slight decrease in selectivity [246]. , 179) [247]. t. t. 37 Asymmetric induction in azirine formation. 38) produced substantial quantities of phenylazirine 181 [248, 249]. Subsequently, the method was adapted to be more amenable to the preparative scale, as exemplified by the synthesis of the trifluoromethylphenylazirine 184, which was carried out on a 10-gram scale [250]. , 182) through sequential bromination, azide displace- j45 j 2 Three-Membered Heterocycles.
Meso aziridines can be enantioselectively desymmetrized using a dimeric salen yttrium catalyst in near quantitative yield and excellent enantioselectivity [161]. 12 Yield data for ring opening of aziridines with benzylamine. Entry Reagent/catalyst Solvent Time (h) Yield (%) Reference 1 2 3 B(C6F5)3 CAN PBu3 CH3CN CH3CN H2O/CH3CN 12 3 12 99 93 99 [136] [137] [138] j33 j 2 Three-Membered Heterocycles. 13 Yield data for ring opening of aziridines with azide. 25 Ring opening of aziridines with azide.
27 atm (400 psi)] and elevated temperatures (90 C) are required. Nevertheless, the catalyst appears to be easily isolated and recycled without loss of activity [215]. Nitrogen and sulfur can also be introduced via ring expansion strategies. 33) [216]. The iminothiazolidine nucle- j39 j 2 Three-Membered Heterocycles. t. Ph Me N Ph Me O Me 141 O 72% 1. NaH, THF, 0°C H Ph 143 Me 2. 32 Carbonyl insertions into aziridines. t. 33 Insertion of nitrogen and sulfur into aziridines. us [217] can be derived from aziridines at room temperature using a palladium(II) acetate/triphenylphosphine catalyst system.