104599-76-0

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 387-45-1 2-chloro-6-fluorobenzaldehyde 
• 79455-63-3 2-chloro-6-fluorobenzoyl chloride 
• 104600-20-6 2-(2-Chloro-6-fluoro-benzoyl)-malonic acid diethyl ester 

Downstream Products

• 104600-13-7 (Z)-2-(2-Chloro-6-fluoro-benzoyl)-3-ethoxy-acrylic acid ethyl ester 
• 104599-87-3 2-(2-Chlor-6-fluorbenzoyl)-3-cyclopropylaminoacrylsaeure-ethylester 

Relevant academic research and scientific papers

Unusual anion effects in the iron-catalyzed formation of 3-hydroxyacrylates from aromatic aldehydes and ethyl diazoacetate

Due to the lability of one of the CO ligands in irans-[Fe(PNP)(CO) 2Cl]+ this compound is an efficient catalyst for the coupling of a series of aromatic aldehydes with ethyl diazoacetate (EDA), which give, in most cases, selectively 3-hydroxyacrylates rather than β-oxo esters. This reaction is strongly dependent on the nature of the counterion, Whereas with BF4- the reaction proceeds with conversions up to 90%, in the case of the counterions NO3-, CF 3COO-, CF3SO3-, SbF 6-, and BAr'4- [Ar' = 3,5-(CF 3)2C6H3] no reaction took place. In the case of PF6- only up to 20% conversion was achieved. A conceivable mechanism for the coupling of aromatic aldehydes with EDA was established by means of DFT/B3LYP calculations, which allowed the rationalization of both the chemoselectivity and the role of the counterions.

Cycloaracylation of Enamines, I. - Synthesis of 4-Quinolone-3-carboxylic Acids

Starting with o-halobenzoyl chlorides 4 and open-chain secondary enamines 5, a new synthesis of 4-quinolone-3-carboxylic acids 12 is described.The reaction of 7-haloquinolone-3-carboxylic acids 12a-k with aliphatic amines 14 produces highly active antibacterial 7-aminoquinolone-3-carboxylic acids 15.The main product of the 1-cyclopropyl series, "ciprofloxacin" (15a), is being developed as a broad-spectrum chemotherapeutic agent.