Artificial Macrocycles by Ugi Reaction and Passerini Ring Closure
نویسندگان
چکیده
منابع مشابه
Investigation of the Passerini and Ugi reactions in β-lactam aldehydes. Synthetic applications.
Passerini (P-3CR) and Ugi (U-4CR) reactions were investigated in 4-oxoazetidine-2-carboxaldehydes, affording the corresponding Passerini and Ugi adducts with moderate diastereoselectivity in high yields. Fortunately, the obtained mixtures of isomers syn/anti were separated in most cases. The scope of both IMCRs has been studied using a variety of isocyanides, carboxylic acids and amines. Ugi ad...
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A practical three-step protocol for the assembly of triazolobenzodiazepine-fused diketopiperazines and hydantoins has been developed. The synthesis of these tetracyclic ring systems was initiated by an Ugi reaction, which brought together all necessary functionalities for further transformations. The Ugi adducts were then subjected to a base-induced ring closing and an intramolecular azide-alky...
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Ammonia in the tetrazole Ugi variation together with α-amino acid methyl ester-derived isocyanides provides tetrazolopiperidinones in good to high yields in one pot. The scope and limitations of this reaction were investigated by performing >70 reactions. The scaffold is useful to fill high-throughput screening decks and in structure-based drug design.
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متن کاملTwo-Step Macrocycle Synthesis by Classical Ugi Reaction
The direct nonpeptidic macrocycle synthesis of α-isocyano-ω-amines via the classical Ugi four-component reaction (U-4CR) is introduced. Herein an efficient and flexible two-step procedure to complex macrocycles is reported. In the first step, the reaction between unprotected diamines and isocyanocarboxylic acids gives high diversity of unprecedented building blocks in high yield. In the next st...
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ژورنال
عنوان ژورنال: The Journal of Organic Chemistry
سال: 2016
ISSN: 0022-3263,1520-6904
DOI: 10.1021/acs.joc.6b01430