16078-38-9

Upstream product

• 29724-68-3 1-benzoyl-1,2-dihydroquinoline 
• 767-92-0 decahydroquinoline 
• 635-46-1 1,2,3,4-tetrahydroisoquinoline 
• 98-88-4 benzoyl chloride 
• 330467-78-2 1-(2-bromobenzoyl)-1,2,3,4-tetrahydroquinoline 
• 292638-85-8 acrylic acid methyl ester 
• 333349-63-6 1-(2-iodobenzoyl)-1,2,3,4-tetrahydroquinoline 
• 60-29-7 diethyl ether 
• 93-89-0 benzoic acid ethyl ester 
• 65-85-0 benzoic acid 
• 4169-19-1 1-acetyl-1,2,3,4-tetrahydroquinoline 
• 123206-77-9 N-<3-(o-bromophenyl)propyl>methoxylamine 

Downstream Products

• 21863-32-1 N-benzyltetrahydroquinoline 
• 99293-89-7 N-benzoyl-1,2-dihydroquinolin-4(3H)-one 
• 24206-41-5 (4-hydroxy-3,4-dihydroquinolin-1(2H)-yl)(phenyl)methanone 
• 73153-66-9 N-(4-(methylthio)phenyl)benzamide 
• 347339-21-3 N-(4-(4-chlorophenoxy)phenyl)benzamide 
• 16466-44-7 N-ethyl-N-phenylbenzamide 
• 93-98-1 N-phenyl benzoyl amide 
• 582-78-5 N-(4-methylphenyl)benzamide 

Relevant academic research and scientific papers

An efficient procedure for chemoselective amidation from carboxylic acid and amine (ammonium salt) under mild conditions

Presented here is an efficient one-pot and catalyst-free procedure for the synthesis of amides starting from carboxylic acids and amine/ammonium salts using 2,2-dichloro-1,3-diisopropylimidazolidine-4,5-dione as the coupling agent. Reactions can proceed smoothly even with those bearing thermosensitive group(s) at ambient temperature, and the corresponding products of primary, secondary and tertiary amides can be afforded in moderate to excellent yields of up to 96%.

Direct Amidation of Esters by Ball Milling**

The direct mechanochemical amidation of esters by ball milling is described. The operationally simple procedure requires an ester, an amine, and substoichiometric KOtBu and was used to prepare a large and diverse library of 78 amide structures with modest to excellent efficiency. Heteroaromatic and heterocyclic components are specifically shown to be amenable to this mechanochemical protocol. This direct synthesis platform has been applied to the synthesis of active pharmaceutical ingredients (APIs) and agrochemicals as well as the gram-scale synthesis of an active pharmaceutical, all in the absence of a reaction solvent.

Intensified Microwave-Assisted N-Acylation Procedure - Synthesis and Activity Evaluation of TRPC3 Channel Agonists with a 1,3-Dihydro-2H-benzo[d]imidazol-2-one Core

Upon controlled microwave heating and using cyanuric chloride as a coupling reagent, an efficient amidation procedure for the synthesis of 1,3-dihydro-2H-benzo[d]imidazol-2-one-based agonists of TRPC3/6 ion channels has been developed. Compared to the few conventional protocols, a drastic reduction in processing time from ca. 2 days down to 10 minutes was achieved accompanied by significantly improved product yields. The robustness of the method was confirmed by 18 additional examples including aromatic, aliphatic, and heterocyclic amines and acids. The obtained agonists were screened for biological activity at 1 μM concentration and few structure-activity relations have been established.

AlMe3-promoted formation of amides from acids and amines

In the presence of AlMe3, amines can be directly coupled with acids through dimethylaluminum amide intermediates to form the corresponding amides. A wide range of amines and acids including less nucleophilic amines, bulky amines, unprotected se

Development of radical addition-cyclization-elimination reaction of oxime ether and its application to formal synthesis of (±)-martinelline

Radical addition-cyclization-elimination (RACE) reaction of oxime ether carrying unsaturated ester provides a novel method for the construction of pyrroloquinoline. Treatment of oxime ethers with Bu3SnH and AIBN gave N-norpyrroloquinoline as a major product, which was also obtained by the radical reaction of the corresponding hydrazone and imine. The radical reaction of aldehyde and ketone carrying unsaturated ester proceeded stereoselectively to give cis-furoquinolines and cis-hydroxyesters. The RACE reactions by using each of Bu3SnNMe2, Bu3SnD, and/or D2O were also examined in order to propose a reaction pathway to N-norpyrroloquinoline. Furthermore, the synthetic utility of RACE reaction is demonstrated by preparation of a key intermediate for the synthesis of (±)-martinelline.

Displacements at the Nitrogen of Lithioalkoxylamides by Organometallic Reagents

The conversions of N-(o-bromobenzyl)methoxylamine to N-acetylbenzoazetine (1), of N-methoxylamine to N-acetyltetrahydroquinoline (2), and N-methoxylamine to N-acetylbenzazapine (3) illustrate the use of this displacement reaction to form nitrogencontaining rings in an exocyclic reaction mode.An X-ray structural determination is reported for 1.The formations of anilides by amination of aromatic organolithium reagents with lithium methoxylamide is also reported.Lithium reagents are found to be more effective than Grignard, copper, or zinc reagents in these displacement, and the yields decrease as the size of the substituents around nitrogen increases.The endocyclic restriction test is used to show that this displacement on nitrogen cannot occur within the endocyclic confines of a seven-membered ring.A SN2 reaction pathway in a lithium complex is considered to be supported by these results.

Microbiological Transformations, Part 6. Microbiological Transformations of Acyl Derivatives of Indoline, 1,2,3,4-Tetrahydroquinoline, 1,2,3,4-Tetrahydroisoquinoline and 2,3,4,5-Tetrahydro-1H-1-benzazepine with the Fungus Cunninghamella elegans

Incubation of N-benzoyl and N-(p-toluoyl)indoline with Cunninghamella elegans resulted in reductive cleavage with the formation of indoline and the corresponding benzyl alcohol.N-Acetylindoline underwent normal benzylic hydroxylation ond open chain analogues of N-(p-toluoyl)indolines were hydroxylated at the aryl methyl group by C. elegans.The fungus effected benzylic oxidation at the 4-position on N-benzoyl-1,2,3-tetrahydroquinoline and in N-benzoyl-1,2,3,4-tetrahydroisoquinoline derivatives.N-(p-Toluoyl)-1,2,3,4-tetrahydroquinoline and N-(p-ethylbenzoyl)-1,2,3,4-tetrahydroisoquinoline were, however, hydroxylated at the alternative 4'-benzylic position.Incubation of N-(p-toluoyl)-2,3,4,5-tetrahydro-1H-1-benzazepine with C. elegans gave 5-hydroxy-N-(p-toluoyl)-2,3,4,5-tetrahydro-1H-1-benzazepine

Bicyclo nitrogenheterocyclic substituted sulfofluoresceins, fluoresceins and xanthenes

There are described novel dye compounds which are represented by the formula STR1 wherein A is STR2 X is H, alkyl, aryl such as phenyl or naphthyl, or substituted aryl; W is H or alkyl; R is H or alkyl; Z and Y are each H or monovalent radicals; l and p are each 1 or 2 and m and n are each integers of from 2-6.