107616-19-3

Upstream product

• 552-16-9 ortho-nitrobenzoic acid 
• 106-95-6 allyl bromide 
• 107-18-6 allyl alcohol 
• 610-14-0 2-nitrobenzyl chloride 

Downstream Products

• 32704-22-6 2-allyl-phenylamine 
• 103441-67-4 1-allyl-2-nitro-benzene 
• 98-95-3 nitrobenzene 
• 552-16-9 ortho-nitrobenzoic acid 
• 1620682-41-8 2-methylallyl 2-nitrobenzoate 
• 1620682-44-1 2-(methoxycarbonyl)allyl 2-nitrobenzoate 
• 22311-55-3 1-(2-methylallyl)-2-nitrobenzene 
• 1620682-68-9 C₁₈H₁₄N₂O₈ 
• 111500-05-1 1-((E)-3-(2-nitrophenyl)prop-1-enyl)benzene 
• 142336-23-0 (E)-1-(buta-1,3-dien-1-yl)-2-nitrobenzene 
• 101320-93-8 allyl-2-iodobenzoate 
• 188578-83-8 (2S,4R)-2-(2-Allyloxycarbonyl-phenylcarbamoyl)-4-hydroxy-pyrrolidine-1-carboxylic acid allyl ester 
• 188578-86-1 (1S,4S)-5-(2-Allyloxycarbonyl-phenyl)-6-oxo-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid allyl ester 
• 188578-89-4 2-(2-Carboxyphenyl)-2,5-diazabicyclo[2.2.1]heptan-3-one 

Relevant academic research and scientific papers

Palladium(0)-catalyzed intramolecular decarboxylative allylation of ortho nitrobenzoic esters

A Pd/Ag bimetallic system has been developed for the decarboxylative allylation of ortho-nitrobenzoic esters in an intramolecular fashion. In contrast to the typical sp2-sp3 cross-coupling approach which requires air and moisture sensitive preformed organometallic reagents, we provide an alternative route to the synthesis of ortho-allyl nitroarenes from the corresponding ortho-nitrobenzoic acid derivatives. The reaction proceeds through a mechanistically distinct decarboxylative metalation pathway. A cooperative reactivity of palladium and silver is crucial for the reaction outcome.

An unexpected Mitsunobu reaction. A direct route to the 2,5-diazabicyclo[2.2.1]heptan-3-one skeleton as a γ-lactam mimic of β-lactam antibiotics

Treatment of anilides of N-protected (2S,4R)-4-hydroxyproline, e.g. 1, with thioacetic acid under Mitsunobu conditions gives, unexpectedly, 2,5-diazabicyclo[2.2.1]heptan-3-ones, e.g. 2, the products of intramolecular cyclisation. However, the less acidic N-benzylamides of these proline derivatives, e.g. 7, are not sufficiently acidic and the hydrazido anion generated in the Mitsunobu reaction displaces the activated hydroxy group in an intermolecular reaction to give 8. The bicyclic γ-lactams are potential analogues of the β-lactam antibiotics and suitable derivatives 9, 10,11 and 12 are found to be competitive inhibitors of class A and C β-lactamases, with Ki as low as 70 μM.

Carbapenem antibiotic compounds

A carbapenem compound of the formula (I) STR1 wherein: R1 is 1-hydroxyethyl, 1-fluoroethyl or hydroxymethyl; R2 is hydrogen or C1-4 alkyl; R3 is hydrogen or C1-4 alkyl; R4 is hydroxy or carboxy; and the phenyl ring is optionally further substituted by one or two substituents selected from halo, cyano, C1-4 alkyl, nitro, hydroxy, carboxy, C1-4 alkoxy, trifluoromethyl, C1-4 alkoxycarbonyl, carbamoyl, C1-4 alkylcarbamoyl, di-C1-4 alkylcarbamoyl, amino, C1-4 alkylamino, di-C1-4 alkylamino sulphonic acid, C1-4 alkylS(O)n --(wherein n is 0-2), N-C1-4 alkanesulphonamido, C1-4 alkanoylamino and C1-4 alkanoyl(N-C1-4 alkyl)amino: provided that the phenyl ring is substituted by at least one carboxy; or a pharmaceutically acceptable salt or in vivo hydrolysable ester thereof.