49681-37-0

Upstream product

• 64-18-6 formic acid 
• 2217-40-5 1,2,3,4-tetrahydronaphthalen-1-amine 
• 77287-34-4 formamide 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 7677-24-9 trimethylsilyl cyanide 
• 529-33-9 1,2,3,4-Tetrahydro-1-naphthol 

Downstream Products

• 602262-90-8 1-isocyano-1,2,3,4-tetrahydronaphthalene 

Relevant academic research and scientific papers

Leuckart-Wallach Route Toward Isocyanides and Some Applications

Isocyanide-based multicomponent reactions (IMCR) are among the most important chemical reactions to efficiently generate molecular diversity and have found widespread use in industry and academia. Generally, isocyanides are synthesized in 1-2 steps starting from primary amines. Here, we provide experimental detail on an alternative approach toward formamides and, thus, isocyanides via the Leuckart-Wallach reaction in an improved variation. The resulting >50 synthesized and characterized formamides are useful starting materials for IMCR, as well as other chemistries. The advantage of using the Leuckart-Wallach pathway to formamides and isocyanides is the lower price, on average, of the starting materials, as well as their differential and complementary structural diversity, as compared to the primary amine pathway.

Metabolic Fate of the Isocyanide Moiety: Are Isocyanides Pharmacophore Groups Neglected by Medicinal Chemists?

Despite the isolation of hundreds of bioactive isocyanides from terrestrial fungi and bacteria as well as marine organisms, the isocyanide functionality has so far received little attention from a medicinal chemistry standpoint. The widespread tenet that isocyanides are chemically and metabolically unstable has restricted bioactivity studies to their antifouling properties and technical applications. In order to confirm or refute this idea, the hepatic metabolism of six model isocyanides was investigated. Aromatic and primary isocyanides turned out to be unstable and metabolically labile, but secondary and tertiary isocyanides resisted metabolization, showing, in some cases, cytochrome P450 inhibitory properties. The potential therefore exists for the secondary and tertiary isocyanides to qualify them as pharmacophore groups, in particular as war-heads for metalloenzyme inhibition because of their potent metal-coordinating properties.

Transamidation of primary amides with amines using hydroxylamine hydrochloride as an inorganic catalyst

Metal-free catalysis: A method for the transamidation of primary amides with primary or secondary amines provides access to secondary and tertiary amides, by utilizing catalytic quantities of hydroxylamine hydrochloride to activate the chemically robust primary amide group (see scheme). A mechanism of primary amide activation through a hydrogen-bonding complex is proposed. Copyright

A novel modification of the Ritter reaction using trimethylsilyl cyanide

A new modification of the Ritter reaction using trimethylsilyl cyanide (Me3SiCN) is described, which converts alcohols to their corresponding formamides in high yields using a convenient procedure. The reaction conditions and mechanism are discussed. In some cases, new formamides are synthesized which cannot be prepared by the classical Ritter reaction.

1-Benzoyl-3-(1,2,3,4-tetrahydro-4-oxo-1-naphthyl)-urea, a novel and useful intermediate for the preparation of animal growth promoting agents

This invention relates to 1-benzoyl (and 1-substituted benzoyl)-3-(1,2,3,4-tetrahydro-4-oxo-1-naphthyl)ureas, novel and useful intermediates for the preparation of 1,2,3,4-tetrahydro-4-oxo-1-naphthylurea and certain derivatives thereof. The above tetrahydro-4-oxo-1-naphthyl-urea and certain derivatives thereof are animal growth promoting agents. This invention further relates to methods of preparation of said 1-benzoyl (and 1-substituted benzoyl) 3-(1,2,3,4-tetrahydro-4-oxo-1-naphthyl)ureas.