59562-41-3

Upstream product

• 97-00-7 1-chloro-2,4-dinitro-benzene 
• 108-59-8 malonic acid dimethyl ester 
• 99-65-0 meta-dinitrobenzene 
• 868-26-8 dimethyl 2-bromomalonate 
• 18424-76-5 dimethyl malonate sodium salt 

Downstream Products

• 203061-15-8 2-(4-amino-2-nitrophenyl)propane-1,3-diol 
• 610315-42-9 2-allyl-2-(2,4-dinitro-phenyl)-malonic acid dimethyl ester 
• 115876-28-3 2-(2,4-Diamino-phenyl)-propane-1,3-diol 

Relevant academic research and scientific papers

A direct entry to the 1-methoxyindole skeleton and to the corresponding indoles by a novel rearrangement: General syntheses of substituted 1-methoxyindoles

A short and efficient route to 1-methoxyindoles via a novel rearrangement is disclosed. This route involves only three steps from commercially available nitro compounds. The methodology is also generalized with a variety of examples to afford a series of

A direct synthesis of 2-arylpropenoic acid esters having nitro groups in the aromatic ring: A short synthesis of (±)-coerulescine and (±)-horsfiline

A short synthesis of 2-arylpropenoic acid esters that possess nitro groups in their phenyl ring using common and less expensive reagents is described. The usefulness of this methodology is substantiated by the efficient total syntheses of (±)-coerulescine and (±)-horsfiline from the 2-arylpropenoic acid esters obtained.

Synthesis of nitrogen and sulfur analogues of the seco-CI alkylating agent

Two complementary syntheses of amino seco-CI (CI = 1a,2,3,5-tetrahydro-1H-cycloprop[1,2-c]indol-5-one) alkylating agents starting from isomeric chloronitrobenzoic acids are reported. Further reactions of these compounds, including diazotisation to phenol and thiophenol derivatives, and alkylation and acylation reactions relevant to the preparation of pro-drug forms are also described.

Synthesis of 2-(2,6-dinitrophenyl)malonates, -acetates and acetonitrile by copper-mediated vicarious nucleophilic substitution

A regioselective, vicarious nucleophilic substitution of 1,3- dinitrobenzene with α-bromo- and iodocarbanions proceeds in the presence of copper(1) tert-butoxide and pyridine giving 2,6-dinitrophenylmalonates, 2,6- dinitrophenylacetates or 2,6-dinitrophenylacetonitrile as the only isomers from bromomalonate esters, bromoacetate esters, iodoacetate esters or iodoacetonitrile, respectively. Without copper(I) tert-butoxide, the 4- substituted isomer is the only product. We believe that the reaction proceeds via a σ-adduct of 1,3-dinitrobenzene and halocarbanion from which hydrogen and halogen are eliminated. This elimination is dependent upon the concentration of copper(I) tert-butoxide.