204930-39-2

Upstream product

• 95-77-2 3,4-dichlorophenol 
• 88-10-8 N,N-diethylcarbamyl chloride 

Downstream Products

• 204930-40-5 Diethyl-carbamic acid 3,4-dichloro-2-methyl-phenyl ester 
• 51571-16-5 5,6-dichloro-2-hydroxybenzaldehyde 

Relevant academic research and scientific papers

1,5-O → N Carbamoyl Snieckus-Fries-Type Rearrangement

The reaction of o-lithiated O-aryl N,N-diethylcarbamates with (hetero)aromatic nitriles gives rise to functionalized salicylidene urea derivatives in high yields through a new 1,5-O → N carbamoyl migration. This Snieckus-Fries-type rearrangement nicely complements previously known O → C and O → O related shifts. In addition, when dimethylmalononitrile is used as the electrophilic partner, the carbamoyl shift is preferred over the expected transnitrilation reaction.

ARYL HETEROCYCLIC COMPOUNDS AS KV1.3 POTASSIUM SHAKER CHANNEL BLOCKERS

A compound of Formula (I), or a pharmaceutically-acceptable salt thereof, is described, wherein the substituents are as defined herein. Pharmaceutical compositions comprising the same and method of using the same are also described.

ARYLMETHYLENE HETEROCYCLIC COMPOUNDS AS KV1.3 POTASSIUM SHAKER CHANNEL BLOCKERS

A compound of Formula (I) or a pharmaceutically acceptable salt thereof is described, wherein the substituents are as defined herein. Pharmaceutical compositions comprising the same and method of using the same are also described.

ARYLMETHYLENE AROMATIC COMPOUNDS AS KV1.3 POTASSIUM SHAKER CHANNEL BLOCKERS

A compound of Formula (I), or a pharmaceutically acceptable salt thereof, is described, wherein the substituents are as defined herein. Pharmaceutical compositions comprising the same and method of using the same are also described.

ARYL HETEROBICYCLIC COMPOUNDS AS KV1.3 POTASSIUM SHAKER CHANNEL BLOCKERS

A compound of Formula (I), or a pharmaceutically acceptable salt thereof, is described, where the substituents are as defined herein. Pharmaceutical compositions including the same and method of using the same are also described.

ARYL HETEROBICYCLIC COMPOUNDS AS KV1.3 POTASSIUM SHAKER CHANNEL BLOCKERS

A compound of Formula (I), or a pharmaceutically acceptable salt thereof, is described, where the substituents are as defined herein. Pharmaceutical compositions including the same and method of using the same are also described.

MLL1 INHIBITORS AND ANTI-CANCER AGENTS

The present invention provides a compound of Formula (I): or an enantiomer, an enantiomeric mixture, or a pharmaceutically acceptable salt thereof; wherein the variables are as defined herein. The present invention further provides pharmaceutical composit

Experimental and computational study of the 1,5-o → n carbamoyl snieckus-fries-type rearrangement

The reactions of o-lithiated O-aryl N,N-diethylcarbamates with different C-N multiple bond electrophiles have been thoroughly studied. A 1,5-O → N carbamoyl shift, a new variation of the anionic Fries-type rearrangement, takes place when nitriles, imines, or alkylcarbodiimides are employed. In these cases, the carbamoyl group plays a dual role as a directing group, building up a variety of functional groups through the 1,5-O → N carbamoyl migration. On the other hand, the use of iso(thio)cyanates and arylcarbodiimides led to non-rearranged o-functionalized Oarylcarbamates. This reactivity was further computationally explored, and the governing factor could be traced back to the relative basicity of the alternative products (migrated vs nonmigrated substrates). This exploration also provided interesting insights about the degree of complexation of the lithium cations onto these substrates. A new access to useful 2-hydroxybenzophenone derivatives has also been developed.

ortho-Lithiation Reactions of O-(3,n-Dihalophenyl) N,N-Diethylcarbamates: Synthesis of Dihalosalicylamides and 2,3,n-Trihalophenol Derivatives

New dihalosalicylamides and trihalophenol derivatives have been synthesized from easily available O-(3,n-dihalophenyl) N,N-diethylcarbamates by using a directed ortho-metalation (DoM) strategy. The o-lithiation reactions with sBuLi take place regioselectively at the doubly activated C-2 position, which demonstrates the ability of O-carbamates as directed metalating groups. In addition, highly functionalized arylnitriles were accessed from organolithium intermediates by using a tandem transnitrilation/SNAr reaction sequence.

Transition metal catalysed cross-coupling between benzylic halides and aryl nucleophiles. Synthesis of some toxicologically interesting tetrachlorobenzyltoluenes

The aryl-benzyl cross-coupling in the presence of copper-, nickel- and palladium-catalysts has been investigated with a number of chlorine- and methyl-substituted arylmetal compounds ArM (M = MgBr, ZnCl) and (substituted) benzylic halides ArCH2X. The results have been applied in the selective synthesis of some toxicologically interesting tetrachlorobenzyltoluenes.