34161-90-5

Upstream product

• 675578-51-5 N-(p-toluenesulfonyl)-2-amino-3-hydroxymethylnaphthalene 
• 5959-52-4 2-Amino-3-naphthoic acid 
• 941-55-9 4-toluenesulfonyl azide 
• 66-99-9 β-naphthaldehyde 
• 141281-58-5 3-Amino-2-(hydroxymethyl)naphthalene 
• 98-59-9 p-toluenesulfonyl chloride 
• 60178-65-6 3-((4-methylphenyl)sulfonamido)-2-naphthoic acid 
• 675578-50-4 N-p-toluenesulfonyl-2-aminonaphthalene-3-carboxylic acid methyl ester 
• 21597-54-6 Methyl 3-amino-2-naphthoate 

Downstream Products

• 675578-52-6 N-allyl-N-(p-toluenesulfonyl)-2-amino-3-formylnaphthalene 
• 402822-79-1 N-allyl-N-(p-toluenesulfonyl)-2-amino-3-ethenylnaphthalene 
• 1242061-63-7 C₃₁H₃₀N₂O₂S 
• 1448809-07-1 2-(iodomethylene)-1-tosyl-1H-benzo[f]indol-3(2H)-one 
• 1448808-97-6 1-(2-(tosylamino)naphthalen-3-yl)prop-2-yn-1-ol 
• 1439383-93-3 1-tosyl-1H-naphtho[2,3-b]azepin-3(2H)-one 
• 1439384-26-5 N-(3-formylnaphthalen-2-yl)-4-methyl-N-(prop-2-yn-1-yl)benzenesulfonamide 

Relevant academic research and scientific papers

Visible-Light-Driven Neutral Nitrogen Radical Mediated Intermolecular Styrene Difunctionalization

A neutral nitrogen radical-mediation strategy, wherein the existing N-H moiety of substrates serves as a neutral nitrogen radical precursor to enable room-temperature intermolecular radical difunctionalization of styrenes under photoredox catalysis, is reported. The reaction shows high functional group tolerance and substrate scope with respect to both components, giving the corresponding products with generally good yields. Preliminary control experiments and DFT calculations are performed to explain the reaction mechanism.

Phosphine-Catalyzed Reaction between 2-Aminobenzaldehydes and Dialkyl Acetylenedicarboxylates: Synthesis of 1,2-Dihydroquinoline Derivatives and Toward the Development of an Olefination Reaction

A series of 1,2-dihydroquinolines were synthesized in good to excellent yields by reacting 2-aminobenzaldehyde derivatives and dialkyl acetylenedicarboxylates with catalytic amounts of phosphine. This reaction was rendered catalytic by the selective in situ phosphine oxide reduction with the use of phenylsilane. Furthermore, with the same starting materials and with an additional role of the reducing agent, a new olefination reaction was discovered. Hydrogen/deuterium (H/D) exchange experiments revealed the possible mechanism of this reaction.

Amphoteric 2-(sulfonylamino)benzaldehydes, secondary amines and isocyanides in the multicomponent synthesis of elusive N-alkyl-2,3-diaminoindoles

A novel interrupted Ugi reaction between ortho-sulfonylaminated aryl aldehydes, secondary amines, and isocyanides affords in good to high yields N-alkyl-2,3-diaminoindoles, providing access to a so far unexplored area of the indole chemical space. With only one single chemical operation, this novel reaction affords a broad gamma of substituted 2,3-diaminoindoles with five points of diversity. The success of this novel multicomponent transformation lies in presence of the amphoteric sulfonylamino group, which sequentially acts as a Br?nsted acids and as a nucleophile the lack of need for additional catalysts and the high atom economy, with the loss of only one molecule of water, renders this approach a very effective one.

Iridium-Catalyzed ortho-C(sp2)-H Amidation of Benzaldehydes with Organic Azides

An iridium-catalyzed ortho-C(sp2)-H amidation reaction of benzaldehydes with organic azides has been developed. A catalytic amount of 3,5-di(trifluoromethyl)aniline was used to promote the Ir-catalyzed directed C-H amination reaction through a transient aldimine intermediate. This reaction tolerates a broad scope of benzaldehyde substrates and works well with a range of aryl- and alkylsulfonyl azides.

1-(2′-Anilinyl)prop-2-yn-1-ol rearrangement for oxindole synthesis

A synthetic method that relies on NIS (N-iodosuccinimide)-mediated cycloisomerization reactions of 1-(2′-anilinyl)prop-2-yn-1-ols to gem-3-(diiodomethyl)indolin-2-ones and 2-(iodomethylene)indolin-3-ones has been developed. The reactions were shown to be chemoselective, with secondary and tertiary alcoholic substrates exclusively giving the 3- and 2-oxindole products, respectively. In the case of the latter, the transformation features an unprecedented double 1,2-OH and 1,2-alkyl migration relay. Density functional theory (DFT) calculations based on proposed iodoaminocyclization species provide insight into this unique divergence in product selectivity. Copyright

Nucleophilic cycloaromatization of ynamide-terminated enediynes

Introduction of a nitrogen atom at one of the acetylenic termini of 10-, 11-, 12-, and 13-membered benzannulated cyclic enediynes results in a complete suppression of the conventional radical Bergman reaction in favor of a polar cycloaromatization. The latter reaction is catalyzed by acids and proceeds via initial protonation of an ynamide fragment. The resulting ketenimmonium cation then cyclizes to produce naphthyl cation, which rapidly reacts with nucleophiles or undergoes Friedel-Crafts addition to aromatic compounds. In alcohols, addition of the nucleophilic solvent across the activated triple bond competes with the cyclization reaction. The ratio of cyclized to solvolysis products decreases with the increase in ring size.

A novel synthesis of substituted quinolines using ring-closing metathesis (RCM): Its application to the synthesis of key intermediates for anti-malarial agents

A method for synthesizing substituted quinolines using ruthenium-catalyzed ring-closing metathesis as a key step has been developed. Substituted 1,2-dihydroquinolines, 4-silyloxy-1,2-dihydroquinoline and 4-methoxy-1,2- dihydroquinoline, were successfully synthesized in excellent yields via ene-ene metathesis and silyl or alkyl enol ether-ene metathesis, respectively. The synthetic intermediates of the antimalarial agents quinine, chloroquine, and PPMP-quinine hybrid were efficiently synthesized by this methodology.

Synthesis of substituted 1,2-dihydroquinolines and quinolines using ene-ene metathesis and ene-enol ether metathesis

We describe a novel and convenient method for quinoline synthesis using ring-closing olefin metathesis (RCM), ene-ene metathesis, and ene-enol ether metathesis. We also report the first example of enol silyl ether-ene metathesis to produce cyclic enol silyl ether. Using this method, versatile substituted quinoline derivatives were readily prepared in excellent yield from anthranilic acid derivatives.