353284-16-9

Upstream product

• 583-68-6 2-bromo-p-toluidine 
• 2258-42-6 formyl acetic anhydride 
• 68-12-2 N,N-dimethyl-formamide 
• 13194-71-3 2-bromo-4-methyl-aniline; hydrochloride 
• 77287-34-4 formamide 
• 109-94-4 formic acid ethyl ester 
• 64-18-6 formic acid 

Downstream Products

• 1295558-52-9 2-ethenyl-4-methylphenyl isocyanide 
• 1295558-77-8 5-methyl-2-phenylsulfanyl-3-phenylsulfanylmethyl-1H-indole 
• 101349-15-9 3,5-dimethyl-2-indolinone 
• 20150-83-8 6-methyl-1,2,3,4-tetrahydroquinolin-2-one 
• 27356-46-3 6-methyl-2-phenyl-quinoline 
• 118714-26-4 6-methyl-2-(p-tolyl)quinoline 
• 81090-31-5 2-bromo-4-methyl-N-methylaniline 
• 1395459-82-1 5-methyl-1H-1,3-benzazaphosphole 

Relevant academic research and scientific papers

An Environmentally Benign, Catalyst-Free N?C Bond Cleavage/Formation of Primary, Secondary, and Tertiary Unactivated Amides

Herein, we report an operationally simple, cheap, and catalyst-free method for the transamidation of a diverse range of unactivated amides furnishing the desired products in excellent yields. This protocol is environmentally friendly and operates under extremely mild conditions without using any promoter or additives. Significantly, this strategy has been implied in the chemoselective synthesis of a pharmaceutical molecule, paracetamol, on a gram-scale with excellent yield. We anticipate that this universally applicable strategy will be of great interest in drug discovery, biochemistry, and organic synthesis.

HCl-mediated transamidation of unactivated formamides using aromatic amines in aqueous media

We report transamidation protocol to synthesize a range of secondary and tertiary amides from weakly nucleophilic aromatic and hetero-aryl amines with low reactive formamide derivatives, utilizing hydrochloric acid as catalyst. This current acid mediated strategy is beneficial because it eliminates the need for a metal catalyst, promoter or additives in the reaction, simplifies isolation and purification. Notably, this approach conventionally used to synthesize molecules on gram scales with excellent yields and a high tolerance for functional groups.

Silver-Catalyzed Chemoselective [4+2] Annulation of Two Isocyanides: A General Route to Pyridone-Fused Carbo- and Heterocycles

A silver-catalyzed chemoselective [4+2] annulation of aryl and heteroaryl isocyanides with α-substituted isocyanoacetamides was developed for the facile and efficient synthesis of 2-aminoquinolones, naphthyridines, and phenanthrolines. A mechanism for this multistep domino reaction is proposed on the basis of a13C-labeling experiment, according to which an unprecedented chemoselective heterodimerization of two different isocyanides generates an α-amidoketenimine intermediate, which undergoes 1,3-amino migration to form an α-imidoylketene, followed by 6 π electrocyclization.

Rh2(II)-Catalyzed Ring Expansion of Cyclobutanol-Substituted Aryl Azides to Access Medium-Sized N-Heterocycles

A new reactivity pattern of Rh2(II)-N-arylnitrenes was discovered that facilitates the synthesis of medium-sized N-heterocycles from ortho-cyclobutanol-substituted aryl azides. The key ring-expansion step of the catalytic cycle is both chemosel

Coupling cyclizations with fragmentations for the preparation of heteroaromatics: Quinolines from o-alkenyl arylisocyanides and boronic acids

Stereoelectronic restrictions on homoallylic ring expansion in alkyne cascades can be overcome by using alkenes as synthetic equivalents of alkynes in reaction cascades that are terminated by C-C bond fragmentation. Implementation of this approach using Mn(iii)-mediated reaction of o-alkenyl isocyanides and boronic acids leads to efficient synthesis of substituted quinolines.

Syntheses of 2-unsubstituted 1h-1,3-benzazaphospholes from n-formyl-2-bromoanilides

The phosphonylation of 2-bromo-formylanilides 1 with triethyl phosphite in the presence of preformed Pd(0)(triethyl phosphite)n catalyst furnished 2-phosphono-formanilides 2 in good yields. Reduction with excess LiAlH4 provided mainl

Photoinduced intramolecular cyclization of o -ethenylaryl isocyanides with organic disulfides mediated by diphenyl ditelluride

Photoinduced reaction of o-ethenylaryl isocyanides with organic disulfides in the presence of diphenyl ditellurides affords the corresponding bisthiolated indole derivatives via a radical cyclization process. The cyclization can proceed at room temperature upon visible-light irradiation and exhibits good tolerance to functional groups. Several organic disulfides also can be employed for this cyclization, and the corresponding bisthiolated indole derivatives are obtained selectively. In addition, the photoinduced reaction of o-ethenylaryl isocyanides with bis(2-aminophenyl) disulfide affords tetracyclic compounds in one portion.