111359-68-3

Upstream product

• 58601-32-4 6-methoxy-2-naphthoyl chloride 
• 3900-45-6 6-methoxy-2-acetylnaphthalene 
• 201230-82-2 carbon monoxide 
• 5111-65-9 2-Bromo-6-methoxynaphthalene 
• 129113-00-4 2-ethynyl-6-methoxynaphthalene 
• 2471-70-7 2-methoxy-6-naphthoic acid 

Downstream Products

• 13101-88-7 6-methoxy-2-naphthylamine 

Relevant academic research and scientific papers

TBAI-catalyzed oxidative synthesis of benzamides from acetophenones and carbinols

An interesting and convenient procedure for the oxidative transformation of acetophenones and carbinols to primary benzamides has been developed. By using tetra-n-butylammonium iodide (TBAI) as the catalyst and tert-butyl hydroperoxide (TBHP) as the oxidant, the desired benzamides were isolated in moderate to good yields in aqueous solution. Notably, not only acetophenones but also propiophenones can be applied as substrates as well. Hence, we believe that this new procedure is not just a catalytic version of the iodine-based method. the Partner Organisations 2014.

Novel and direct transformation of methyl ketones or carbinols to primary amides by employing aqueous ammonia

Figur Presented A novel and direct transformation of aryl, heteroaryl, vinyl, or ethynyl methyl ketones or carbinols to corresponding primary amides has been developed. An iodine-NH3·H2O system was proven to be efficient for this reaction and afforded the expected products with good yields in aqueous media. A tandem Lieben-Haller-Bauer reaction mechanism was involved in this type of reaction and is proposed for the first time.

Palladium-catalyzed synthesis of primary benzamides from aryl bromides via a cyanation and hydration sequence

An interesting and effective procedure for the synthesis of benzamides from aryl bromides has been developed. In the presence of a palladium catalyst, various primary benzamides have been produced in moderate to excellent yields in a one-pot one-step manner.

Naphthalenyl derivatives for hitting P-gp/MRP1/BCRP transporters

Substituted naphthalenyl derivatives bearing oxazole, or thiazole or furyl heteronuclei have been carried out as bioisosters of aryl-oxazoles and -thiazoles derivatives previously reported in order to investigate the role of the hindrance on the activity towards P-gp/BCRP/and MRP1 transporters. In addition, the role of naphthalenyl group to modulate P-gp intrinsic activity of these compounds was ascertained. The results demonstrated that all naphthalenyl derivatives displayed comparable P-gp activity with respect to lead compounds previously characterized in our SAR studies but were less active towards BCRP and MRP1 pumps. In terms of intrinsic activity, the replacement of aryl with naphthalenyl moiety led to P-gp inhibitors, unambiguous or ambiguous substrates on the base of the heteronucleus and the substituent on the naphthalenyl fragment. Indeed, oxazole derivatives were: inhibitors (R = H, F, OH), unambiguous substrates (R = OCH3), or ambiguous substrate (R = Br); thiazole derivatives were: unambiguous substrates (R = OCH3, Br), or ambiguous substrates (R = H, F). Finally furyl derivatives were ambiguous substrates.

Visible Light-Induced Iodine-Catalyzed Transformation of Terminal Alkynes to Primary Amides via C≡C Bond Cleavage under Aqueous Conditions

The visible light-induced iodine-catalyzed oxidative cleavage of the C≡C bond for transforming terminal alkynes into primary amides in the presence of ammonia under aqueous conditions is described. This metal-free protocol which ensued via initial hydroamination of the acetylene bond followed by liberation of diiodomethane (CH2I2) was found to be applicable to aromatic, heteroaromatic and aliphatic alkynes.

Palladium-catalyzed approach to primary amides using nongaseous precursors

A simple protocol is reported for the preparation of primary aryl amides under Pd-catalyzed carbonylation chemistry applying a two-chamber system with crystalline and nontransition metal based sources of carbon monoxide and ammonia. The method is suitable for the synthesis of a number of primary amides with good functional group tolerance. Incorporation of 13CO into the primary amide group was also found to be effective making this approach useful for accessing carbon isotope labeled derivatives.

Method of inhibiting leukotriene biosynthesis by oral administration of p-aminophenols or derivatives thereof

A method is provided for inhibiting leukotriene biosynthesis and thus treating asthma, psoriasis or inflammation by oral administration of p-aminophenols having the structure STR1 wherein m is 0 to 5; X is CH or N; R1 and R2 may be the same or different and are H, lower alkyl, aryl, hydroxy, hydroxyalkyleneoxy, alkylthio, alkoxy, alkanoyloxy, aryloxy, halo, carboxy, alkoxycarbonyl or amido; R3 is H, lower alkyl, alkanoyl or aroyl; and R4 is H, lower alkyl, benzoyl or alkanoyl, and including acid-addition salts thereof, with the proviso that when R4 is benzoyl, R2 is other than H.

Quinoline compounds and compositions thereof

p-Aminophenols are provided having the structure STR1 wherein m is 0 to 5; X is CH or N; R1 and R2 may be the same or different and are H, lower alkyl, aryl, hydroxy, hydroxyalkyleneoxy, alkylthio, alkoxy, alkanoyloxy, aryloxy, halo, carboxy, alkoxycarbonyl or amido; R3 is H, lower alkyl, alkanoyl or aroyl; and R4 is H, lower alkyl or alkanoyl, and including acid-addition salts thereof, with the proviso that when X is CH, m is 0 and R1 is H, and when R4 is H, R2 is other than alkoxy, H or hydroxy, and when R4 is benzoyl, R2 is other than H. These compounds together with the compounds defined in the above proviso are useful as inhibitors of leukotriene production and as such are useful as antiallergy, anti-inflammatory and anti-psoriatic agents.