10286-86-9

Upstream product

• 1143-74-4 N-o-tolylbenzohydroxamic acid 
• 98-88-4 benzoyl chloride 
• 87-63-8 2-chloro-6-methylaniline 
• 88-72-2 1-methyl-2-nitrobenzene 
• 118923-96-9 2-chloro-6-methylphenyl isocyanide 
• 108-88-3 toluene 
• 611-22-3 N-(o-tolyl)hydroxylamine 

Downstream Products

• 66866-01-1 7-chloro-2-phenyl-1H-indole 
• 1025807-12-8 4-(7-chloro-2-phenyl-1H-indol-3-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester 
• 77791-11-8 4-methyl-2-phenyl-1,3-benzoxazole 
• 52159-88-3 1-benzyl-4-methyl-2-phenyl-1H-benzo[d]imidazole 
• 1402938-82-2 (Z)-N-(2-chloro-6-methylphenyl)benzimidoyl chloride 

Relevant academic research and scientific papers

Exploiting the Reactivity of Isocyanide: Coupling Reaction between Isocyanide and Toluene Derivatives Using the Isocyano Group as an N1 Synthon

An unusual oxidative coupling reaction of isocyanide and toluene derivatives using tetrabutylammonium iodide (TBAI) as a catalyst is disclosed. The experimental results and mechanistic study show that the isocyano group acts formally as an N1 synthon during the transformation, thus expanding the reactivity profile of isocyanide.

Palladium-catalyzed synthesis of benzimidazoles and quinazolinones from common precursors

N-(o-Halophenyl)imidoyl chlorides and the corresponding imidates are easily prepared and can be utilized as complementary precursors for the synthesis of important heterocycles. The synthesis of N-substituted benzimidazoles was possible from the palladium

Anxiolytic-like effects of N,N-dialkyl-2-phenylindol-3-ylglyoxylamides by modulation of translocator protein promoting neurosteroid biosynthesis

Novel N,N-disubstituted indol-3-ylglyoxylamides (1-56), bearing different combinations of substituents R1-R5, were synthesized and evaluated as ligands of the translocator protein (TSPO), the 18 kDa protein representing the minimal f

Synthesis and biological evaluation of novel 5(H)-phenanthridin-6-ones, 5(H)-phenanthridin-6-one diketo acid, and polycyclic aromatic diketo acid analogs as new HIV-1 integrase inhibitors

A new series of phenanthridinone derivatives, and diketo acid analogs, as well as related phenanthrene and anthracene diketo acids have been synthesized and evaluated as HIV integrase (IN) inhibitors. Several new β-diketo acid analogs with the phenanthrid

3-(4-Fluoropiperidin-3-yl)-2-phenylindoles as high affinity, selective, and orally bioavailable h5-HT2A receptor antagonists

The development of very high affinity, selective, and bioavailable h5-HT2A receptor antagonists is described. By investigation of the optimal position for the basic nitrogen in a series of 2-phenyl-3-piperidylindoles, it was found that with the basic nitrogen at the 3-position of the piperidine it was not necessary to further substitute the piperidine in order to obtain good binding at h5-HT2A receptors. This meant the compounds no longer had high affinity at the IKr potassium channel, an issue with previous series of 2-aryl-3-(4-piperidyl)indoles. Improvements could be made to oral bioavailability in this series by reduction of the pKa of the basic nitrogen, by adding a fluorine atom to the piperidine ring, leading to 3-(4-fluoropiperidin-3-yl)-2-phenyl-1H-indole (17). Metabolic studies with this compound identified oxidation at the 6-position of the indole as a major route in vitro and in vivo in rats. Blocking this position with a fluorine atom led to 6-fluoro-3-(4-fluoropiperidin-3-yl)-2-phenyl-1H-indole (22), an antagonist with 0.06 nM affinity for h5-HT2A receptors, with bioavailability of 80% and half-life of 12 h in rats.

Novel Reactions: Part I - Facile Synthesis of Substituted ortho-Chloranilines from Nitrobenzene Derivatives

N-Substituted benzo and acetohydroxamic acids (5), prepared from N-arylhydroxylamines and benzoyl or acetyl chloride, react readily with thionyl chloride at low temperature to give ortho-chloroanilide derivatives (6) in good yield.The latter (6) on hydrolysis give ortho-chloroanilines (10).Since the N-arylhydroxylamines are obtained from nitroarenes by partial reduction, the overall reaction amounts to the preparation of 10 from nitroarenes.

NOVEL ORTHOHALOGENATION REACTION. SYNTHESIS OF ORTHOCHLOROARYLAMINES FROM NITROARENES.

Thionyl chloride reacts with N-phenylbenzo and N-phenylaceto-hydroxamic acids at low temperatures to give ortho-chloroanilide derivatives in good yield.

Investigation of the Synthesis of Benzoxazole via Aryne Reaction

The reaction of o- and m-halobenzamides under aryne-forming conditions yielded the corresponding o-hydroxyphenyl amidines instead of the expected benzoxazole derivatives.The amidines, however, were converted to the corresponding benzoxazole either by sublimation or acidic hydrolysis.Evidence is presented that benzoxazoles are initially formed in these reactions but are readily aminated to the corresponding hydroxyphenyl amidines under the highly basic reaction conditions used in these aryne-forming reactions.