16764-13-9

Upstream product

• 4212-33-3 2-(2-nitrophenyl)-1-phenylethanone 
• 17876-76-5 trimethyl(2-nitrobenzyl)silane 
• 100-52-7 benzaldehyde 
• 88-72-2 1-methyl-2-nitrobenzene 

Downstream Products

• 948-65-2 2-phenyl-indole 
• 51308-10-2 α-phenyl-2-aminophenethyl alcohol 
• 4212-33-3 2-(2-nitrophenyl)-1-phenylethanone 
• 1308803-47-5 2-(2-nitrophenyl)-1-phenylpropen-1-one 
• 26211-73-4 (2-methyl-1H-indol-3-yl)phenylmethanone 
• 1429196-08-6 3-methyl-4-(2-nitrophenyl)-5-phenylisoxazole 
• 149913-91-7 allyl α-phenyl-2-<(allyloxycarbonyl)amino>phenethyl carbonate 
• 149913-87-1 allyl α-phenyl-2-aminophenethyl carbonate 
• 835893-34-0 1-deuterio-1-phenyl-2-(2-nitrophenyl)ethene 
• 209979-45-3 2-(2-deuterio-2-phenylethyl)phenyl azide 
• 835893-33-9 1-deuterio-1-phenyl-2-(2-nitrophenyl)ethanol 
• 835893-35-1 2-(2-deuterio-2-phenylethyl)aniline 

Relevant academic research and scientific papers

Synthesis of 2-substituted indole with Hantzsch ester catalyzed by palladium

An efficient reductive cyclization of o-nitrobenzyl ketone compounds was achieved by using a Hantzsch 1,4-dihydropyridine ester as a biomimetic reducing agent in the presence of catalytic palladium on carbon. 2-Substituted indoles were obtained in good yields. Investigation of the mechanism suggests that palladium hydride promotes the reduction of nitro group, and acetic acid was beneficial for the loss of water to produce the intended product. This reaction system can not only broaden the use of Hantzsch 1,4-dihydropyridine ester, but it also provides a novel approach for preparing indole compounds.

Synthesis of new 3-substituted 1-hydroxy-2-phenylindoles using sulfur-containing nucleophiles

The synthesis of new 3-[(acyl(or alkyl)thio)methyl]-1-hydroxy-2-phenylindoles 1 are presented. The substrates 2 obtained by each efficient three-step synthesis were treated, in the presence of SnCl2·2H2O, with nucleophiles such as th

Heterocycle-heterocycle strategies: (2-nitrophenyl)isoxazole precursors to 4-aminoquinolines, 1 H-indoles, and quinolin-4(1 H)-ones

Reductive heterocycle-heterocycle (heterocycle → heterocycle; H-H) transformations that give 4-aminoquinolines, 3-acylindoles, and quinolin-4(1H)-ones from 2-nitrophenyl substituted isoxazoles are reported. When this methodology is applied to 3,5-, 4,5-,

An improved synthesis of 1,2-diarylethanols under conventional heating and ultrasound irradiation

A simple and efficient synthesis of 1,2-diarylethanols has been developed. The procedure involved the reaction between a variety of toluene derivatives and aryl aldehydes under conventional heating and ultrasound irradiation. This procedure possesses seve

Mechanistic studies of intramolecular CH insertion reaction of arylnitrenes: Isotope effect, configurational purity and radical clock studies

In order to reveal the mechanism of the intramolecular CH insertion of arylnitrenes, three experiments were carried out: measurement of isotope effects, determination of the extent of configurational retention and radical clock studies. Irradiation of the deuterium-substituted azide 4-d in an inert solvent exclusively afforded the indolines 5-h and 5-d, in which the kinetic isotope effect kH/kD on the intramolecular CH insertion of the nitrene was evaluated as 12.6-14.7 at room temperature. A chiral Chromatographic analysis of the indoline 11 obtained from the optically active azide (S)-6 revealed that the enantiomeric purity of the starting azide was almost completely lost during the intramolecular CH insertion of the photolytically generated nitrene (enantiomeric excess 10%). The thermolysis of the azide 7 at 180°C mainly gave a mixture of the cyclopropyl ring-opened products 20-22, together with the intramolecular CH insertion product with an intact cyclopropyl ring 19. On the basis of these observations, we concluded that the intramolecular CH insertion of the nitrene proceeds primarily by the hydrogen abstraction-recombination mechanism. We propose, however, a small contribution of the concerted mechanism to the intramolecular CH insertion, based on the solvent dependence of the isotope effect and the extent of the configurational retention. Copyright

New Types of Very Efficient Photolabile Protecting Groups Based upon the [2-(2-Nitrophenyl)propoxy]carbonyl (NPPOC) Moiety

Based upon the photolabile [2-(2-nitrophenyl)propoxy]carbonyl group (NPPOC), a large number of modified 2-(2-nitrophenyl)propanol derivatives substituted at the phenyl ring (see 23-34 and 57-76) as well as at the side-chain (see 85-92 and 95-98) were synthesized to improve the photoreactivity of this new type of photolabile entity. The phenyl moiety was also exchanged by the naphthalenyl group (see 102, 103, 105, 108, 110, 113, and 114), the thienyl substituent (see 115, 117, 118, and 120), and the benzothienyl substituent (see 121). The 2-(2-nitroaryl- and heteroaryl) propanols were converted with diphosgene into the corresponding carbonochloridates, which reacted subsequently with thymidine to the thymidine 5′-(protected carbonates) 123-178 as the main reaction products. In several cases, the corresponding 3′-carbonates and 3′,5′ -dicarbonates 179-212 were also isolated and characterized. Photolysis studies under standardized conditions (see Table) indicated that the rate of photocleavage varies in a broad range depending on the substituents. So far, the thymidine 5′-[2-(5-halo-2-nitrophenyl)propyl carbonates] 127-129, 5′-[2-(nitro[1,1′-biphenyl]3-yl)propyl carbonates] 136-139, 5′-{2-[2-nitro-5-(thianthren-1-yl)phenyl]propyl carbonate} (140), 5′-[2-(5-naphthalenyl-2-nitrophenyl)propyl carbonates] 141 and 142, and 5′-[2-(2-nitro-5-thienylphenyl)propyl carbonates] 143 and 144 showed the best properties regarding fast and uniform deprotection. Since the nucleobases of 213-215 do not influence the photocleavage features, in general, the new type of photolabile building blocks allows in form of their 3′ -phosphoramidites the photolithographic formation of high-quality biochips.

Ruthenium-Catalyzed Dehydrogenative N-Heterocyclization: Indoles from 2-Aminophenethyl Alcohols and 2-Nitrophenethyl Alcohols

Indole derivatives 3 were readily obtained from 2-aminophenethyl alcohols 1 in the presence of 2 mol percent (based on 1) of RuCl2(PPh3)3 under reflux in toluene.Indole (3a) was afforded from 2-aminophenethyl alcohol (1a) quantitatively.Other indoles (3) were also obtained in 73-99percent isolated yields from the corresponding 1, which were easily prepared by condensation between the corresponding 2-nitrotoluenes and aldehydes followed by reduction.During the reaction, a stoichiometric amount of hydrogen was spontaneously evolved into the gas phase.With a heterogeneous and homogeneous binary catalyst system, indoles were afforded in one pot from 2-nitrophenethyl alcohols 2 under a hydrogen atmosphere.

FLUORIDE ION INDUCED REACTIONS OF ORGANOSILANES WITH ELECTROPHILES

Benzyl- 4-picolyl- and phenylallyl(trimethyl)silanes react with electrophiles in the presence of KF/18-crown-6 or silica-TBAF under mild conditions.