79110-02-4

Upstream product

• 529-23-7 o-aminobenzaldehyde 
• 586-78-7 para-nitrophenyl bromide 
• 1016641-93-2 C₁₅H₁₄N₂O₄ 
• 100-01-6 4-nitro-aniline 
• 6630-33-7 ortho-bromobenzaldehyde 
• 34824-58-3 2-(2-bromophenyl)-1,3-dioxolan 

Relevant academic research and scientific papers

Predictive chirality sensing: Via Schiff base formation

Among the large number of chiroptical sensors that have been developed to date, few allow rational determination of the absolute configuration of chiral substrates together with quantitative ee analysis. We have prepared and tested stereodynamic N-aryl aminobenzaldehyde sensors that bind chiral amines via Schiff base formation. The covalent binding of the amine substrate generates a conformational bias in the chromophoric sensor moiety which results in characteristic CD signals. Computational analysis revealed that CD prediction of the sign of the Cotton effect and thus determination of the absolute configuration of the substrate becomes practical with a sterically crowded sensor design because the number of conformations to be considered is largely reduced and the chiroptical sensor response is less sensitive to conformational equilibria. The amplitude of the measured CD signal can be used for quantitative ee analysis of nonracemic amine samples with the help of a calibration curve.

NHC-Organocatalyzed CAr?O Bond Cleavage: Mild Access to 2-Hydroxybenzophenones

A Truce–Smiles rearrangement of acyl-anion equivalents generated by N-heterocyclic carbene (NHC) catalysis has been achieved. The developed method includes CAr?O, CAr?S, or CAr?N bond cleavage for the formation of a CAr?C bond and enables access to 2-hydroxybenzophenones, an important structural motif that is present in several bioactive natural products. By utilizing this procedure, the alkaloid taxilamine was synthesized in three steps. DFT calculations and control experiments support a classical SNAr mechanism with a catalyst-bound Meisenheimer-type intermediate. The method features mild reaction conditions, excellent functional-group tolerance, and a broad substrate scope, including various classes of (hetero)arenes.

QUINOLINONE DERIVATIVES

HIV inhibitory compounds of formula (I) including the stereoisomeric forms thereof, the pharmaceutically acceptable salts, and pharmaceutically acceptable solvates thereof; wherein R1 is cyano; R2 is H, C1-6alkyl, trifluoromethyl, amino, mono- or di-C1-6alkylamino, C1-6alkylamino wherein the C1-6alkyl group can be substituted; X1 is CH or N; R3 is phenyl or pyridyl, each unsubstituted or substituted; R4 is H, C1-6alkyl, (C1-6alkylcarbonyla mino)C1-6alkyl-, Ar, potionally substituted thienyl, furanyl, pyridyl, pyrimidyl, pyrazinyl, pyrrolyl, pyrazolyl, imidazolyl, triazo lyl, oxazolyl, thiazolyl, halo, trifluoromethyl, hydroxy, C1-6alkyloxy, -OPO(OH)2, amino, aminocarbonyl, cyano, -Y1-R6, -Y1-Alk-R6, or -Y1-Alk-Y2-R7; R5 is H, halo, hydroxy or C1-6alkyloxy; or R4 and R5 form -O-CH2-O-; Y1 is O or NR8; Y2 is O or NR9; Alk is bivalent C1-6alkyl; R6 is pyrrolidinyl, piperidinyl, morpho linyl, piperazinyl, 4-C1 -6alkylpiperazinyl, 4-(C1-6alkylcarbonyl)piperazinyl, pyridyl, or imidazolyl; R7 is H, C1-6alkyl, hydroxyC1 -6alkyl, C1-6alkylcarbonyl; R8 and R9 are H or C1-6alkyl; Ar is optionally substituted phenyl; pharmaceut ical compositions comprising the above compounds (I) as active ingredient.

The Preparation of Some 2-Nitroacridines and Related Compounds

The reaction of 2-fluoro-5-nitrobenzaldehyde with a wide variety of arylamines gives, in general, mixtures of the corresponding 2-arylamino-5-nitrobenzaldehydes and their related anils.Both aldehydes and anils readily underwent acid-catalysed cyclization to give the corresponding 2-nitroacridines.The effect of substituent on the rate of cyclization of these aldehydes and of some related anilino-benzaldehydes and -acetophenones has been studied in trifluoroacetic acid solution by means of 1H n.m.r. spectroscopy.A solution of 2-(N-methylanilino)-5-nitrobenzaldehydein trifluoroacetic acid appears to contain a substituted acridinium ion; treatment of this solution with alkali gave 10-methyl-2-nitroacridone. 1H n.m.r. data for a wide variety of substituted 2-nitroacridines are discussed.