Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 3, Pages 1441-1447Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b02984
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Funding
- NIH [2R01GM097082-05]
- Innovative Medicines Initiative [115489]
- European Union's Seventh Framework Programme (FP7)
- EFPIA companies'
- European Union's Horizon research and innovation programme under MSC ITN Accelerated Early Stage Drug Discovery [675555]
- European Union's Horizon research and innovation programme under CoFund ALERT [665250]
- European Regional Development Fund [POIG.02.01.00-12-023/08]
- Egyptian government
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The direct nonpeptidic macrocycle synthesis of a-isocyano-omega-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 step, the a-isocyano-omega-amines undergo a U-4CR with high diversity of aldehydes and carboxylic acids in a one-pot procedure. This synthetic approach is short and efficient and leads to a wide range of macrocycles with different ring sizes.
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