80589-49-7

Upstream product

• 50685-26-2 4-(cyanomethyl)benzoic acid 
• 6232-88-8 4-bromomethylbenzoic Acid 
• 51628-12-7 4-iodophenylacetonitrile 

Downstream Products

• 80589-52-2 (4-Cyanomethyl-benzoylamino)-phenyl-acetic acid ethyl ester 
• 120352-92-3 4-Cyanomethyl-N,N-dimethyl-benzamide 
• 208921-80-6 4-(cyanomethyl)-N,N-diethylbenzamide 
• 52334-43-7 2-(4-cyanomethylphenyl)oxazolo[5,4-b]pyridine 
• 208921-83-9 4-Cyanomethyl-N,N-diethyl-thiobenzamide 
• 208921-82-8 4-Cyanomethyl-N,N-dimethyl-thiobenzamide 
• 200802-49-9 4-Cyanomethyl-N-(2-oxo-1,2-diphenyl-ethyl)-benzamide 
• 80589-54-4 ethyl N-(α-cyano-p-toluoyl)-4-chlorophenylglycinate 
• 80589-55-5 (4-Cyanomethyl-benzoylamino)-(2,4-dichloro-phenyl)-acetic acid ethyl ester 
• 80589-57-7 (4-Cyanomethyl-benzoylamino)-(3,4-dimethoxy-phenyl)-acetic acid ethyl ester 
• 80589-56-6 (4-Cyanomethyl-benzoylamino)-(4-methoxy-phenyl)-acetic acid ethyl ester 
• 80589-53-3 (4-Chloro-phenyl)-(4-cyanomethyl-benzoylamino)-acetic acid methyl ester 
• 80589-60-2 2-(4-Cyanomethyl-benzoylamino)-3-methyl-butyric acid ethyl ester 
• 80589-51-1 methyl N-(α-cyano-p-toluoyl)-4-phenylglycinate 

Relevant academic research and scientific papers

Metathesis-active ligands enable a catalytic functional group metathesis between aroyl chlorides and aryl iodides

Current methods for functional group interconversion have, for the most part, relied on relatively strong driving forces which often require highly reactive reagents to generate irreversibly a desired product in high yield and selectivity. These approaches generally prevent the use of the same catalytic strategy to perform the reverse reaction. Here we describe a catalytic functional group metathesis approach to interconvert, under CO-free conditions, two synthetically important classes of electrophiles that are often employed in the preparation of pharmaceuticals and agrochemicals—aroyl chlorides (ArCOCl) and aryl iodides (ArI). Our reaction design relies on the implementation of a key reversible ligand C–P bond cleavage event, which enables a non-innocent, metathesis-active phosphine ligand to mediate a rapid aryl group transfer between the two different electrophiles. Beyond enabling a practical and safer approach to the interconversion of ArCOCl and ArI, this type of ligand non-innocence provides a blueprint for the development of a broad range of functional group metathesis reactions employing synthetically relevant aryl electrophiles.

From Donor and Acceptor Substituted meta- and para-Xylenes to para-Quinodimethanes and Poly(meta-phenylenevinylene)s

Ortho-, meta- and para-xylenes 1, 13a, 13b and 13c, with donor and acceptor substituents at the α- and α′ positions, lead to a remarkable variety of intermediates and reaction products after deprotonation of the benzylic proton. Thus, the reaction of para-(cyanomethyl)dialkyl[(methylthio)phenylmethylene]ammonium tetrafluoroborates 13a and 13b with sodium hydride affords the para-quinodimethanes 14a and 14b. Poly(meta-phenylenevinylene) 14c can be obtained when starting from 13c. We report the synthesis of para-quinodimethanes 14a and 14b and poly(meta-phenylenevinylene) 14c and describe a successive approach towards meta-phenylenevinylenes of definite length 16b and 17b starting from 12d. Moreover, we compare the stability and reactivity of para-quinodimethane 14a and 14b with those of the ortho-quinodimethane 2 and we focus on the characterization of the resulting donor and acceptor substituted compounds.

Catecholamine surrogates useful as β3 agonists

Compounds of the formula STR1 or pharmaceutically acceptable salts thereof wherein: A is a bond, --(CH 2) n -- or --CH(B)--, where n is an integer of 1 to 3 and B is --CN, --CON(R 9)R 9'' or --CO 2 R 7 ;R 1 is lower alkyl, aryl or arylalkyl;R 2 is hydrogen, hydroxy, alkoxy, --CH 2 OH, cyano, --C(O)OR 7, --CO 2 H, --CONH 2, tetrazole, --CH 2 NH 2 or halogen; STR2 R 3 is hydrogen, alkyl, heterocycle or R 4 is hydrogen, alkyl or B;R 5, R 5'', R 8, R 8'' or R 8"" are independently hydrogen, alkoxy, lower alkyl, halogen, --OH, --CN, --(CH 2) n NR 6 COR 7, --CON(R 6)R 6'', --CON(R 6)OR 6'', --CO 2 R 6, --SR 7, --SOR 7, --SO 2 R 7, --N(R 6)SO 2 R 1, --N(R 6)R 6'', --NR 6 COR 7, --OCH 2 CON(R 6)R 6'', --OCH 2 CO 2 R 7 or aryl; orR 5 and R 5'' or R 8 and R 8'' may together with the carbon atoms to which they are attached form an aryl or heterocycle;R 6 and R 6'' are independently hydrogen or lower alkyl; andR 7 is lower alkyl;R 9 is hydrogen, lower alkyl, alkyl, cycloalkyl, arylalkyl, aryl, heteroaryl; or R 9 and R 9'' may together with the nitrogen atom to which they are attached form a heterocycle; with the proviso that when A is a bond or --(CH 2) n and R 3 is hydrogen or unsubstituted alkyl, then R 4 is B or substituted alkyl. These compounds are beta 3 adrenergic receptor agonists and are useful, therefore for example, in the treatment of diabetes, obesity and gastrointestinal diseases.

Anti-Inflammatory Agents: Part V - Synthesis of Some New 4-(4,5-Disubstituted-oxazol-2-yl)phenylacetic Acids and their Methyl Esters

A series of 4-(4-aryl/alkyl-5-alkoxyoxazol-2-yl)phenylacetic acids (4a-j) has been synthesised by the reaction of appropriately substituted glycinate hydrochlorides (1a-j) with α-cyano-p-toluoyl chloride followed by cyclization and hydrolysis of the resulting N-α-cyano-p-toluoylglycinates (2a-j).Esterification (CH2N2) of the oxazolylphenylacetic acids (4a-g) furnishes the corresponding methyl esters (5a-g).Several compounds in this series show moderate anti-inflammatory activity at one fifth of their LD50 dose in the carrageenin-induced rat paw oedema test.