Schwalbe, Thomas published the artcileSynthesis of a library of Ciprofloxacin analogues by means of sequential organic synthesis in microreactors, Name: Ethyl 3-(dimethylamino)acrylate, the publication is QSAR & Combinatorial Science (2005), 24(6), 758-768, database is CAplus.
The realm of combinatorial chem. is strongly based on the concept of parallel chem. and its ease of automation. Although this batch-type approach in general may be considered a success story, some limitations remain rarely addressable by conventional approaches. Particularly, scaling-up problems such as the resynthesis of multi-gram amounts of active compounds as well as the synthesis of building blocks and scaffolds in large amounts may prove to be problematic. The authors’ expertise in continuous chem. prompted them to develop a micro-reaction system for sequential organic synthesis that should overcome these limitations. In the present contribution a suitable system as well as its application to the first library approach towards (fluoro)quinolone antibiotics, such as Ciprofloxacin, solely using micro-reaction technol. is described. A known one-pot batch procedure for the synthesis of this compound class was split in its individual reaction steps, which were successfully adapted to a continuous conduct. After some optimization studies the overall sequence was suitable for chem. diversification. Particularly it was shown, that the first step of the synthesis – the acylation reaction of a β-dimethylamino acrylate with trifluoro-benzoic acid chloride – was accessible to synthesis of high quantities without any difficulties to yield a primary building block suitable for subsequent library synthesis. In a first diversification step, the Michael addition of a set of primary amines was followed by nucleophilic ring closure providing the difluoroquinolone system, which was subjected to a second diversification step by means of a nucleophilic aromatic substitution reaction. Thus, a number of Ciprofloxacin analogs could be synthesized in good overall yield and purity. Isolated yields ranged from 71 to 85% in the first diversification step and from 59 to 99% in the second step.
QSAR & Combinatorial Science published new progress about 924-99-2. 924-99-2 belongs to esters-buliding-blocks, auxiliary class Alkenyl,Amine,Aliphatic hydrocarbon chain,Ester, name is Ethyl 3-(dimethylamino)acrylate, and the molecular formula is C12H13NO3, Name: Ethyl 3-(dimethylamino)acrylate.
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https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics