132-90-1

Upstream product

• 151475-49-9 N-propenyl-3-butylisoquinolin-1(2H)-one 
• 10283-95-1 N-allylbenzamide 
• 859629-10-0 3-(1-amino-pentyl)-phthalide 
• 855619-99-7 3-butyl-4-hydroxy-3,4-dihydro-2H-isoquinolin-1-one 
• 146470-69-1 (+/-)-3-butyl-3,4-dihydroisoquinolin-1-(2H)-one 
• 55-21-0 benzamide 
• 693-02-7 hex-1-yne 
• 1821-34-7 N-chlorobenzamide 
• 1180487-14-2 (E)-2-(hex-1-ynyl)benzaldehyde O-acetyl-oxime 
• 7664-93-9 sulfuric acid 
• 139583-84-9 N-propenyl-2-methylbenzamide 
• 98-88-4 benzoyl chloride 
• 129118-11-2 N-methoxy-N-methyl-n-pentanamide 
• 57139-25-0 N-methoxy-2-methylbenzamide 

Downstream Products

• 86-80-6 dimethisoquin 

Relevant academic research and scientific papers

Direct access to cobaltacycles via C-H activation: N-chloroamide- enabled room-temperature synthesis of heterocycles

Cobaltacycle synthesis via C-H activation has been achieved for the first time, providing key mechanistic insight into cobalt catalytic chemistry. NChloroamides are used as a directing synthon for cobalt-catalyzed roomtemperature C-H activation and construction of heterocycles. Alkynes as coupling partners allow convenient access to isoquinolones, a class of synthetically and pharmaceutically important compounds. The broad substrate scope enables a diverse range of substitution patterns to be incorporated into the heterocyclic scaffold.

Gold- or Silver-Catalyzed Syntheses of Pyrones and Pyridine Derivatives: Mechanistic and Synthetic Aspects

3-Oxo-5-alkynoic acid esters, on treatment with a carbophilic catalyst, undergo 6-endo-dig cyclization reactions to furnish either 2-pyrones or 4-pyrones in high yields. The regiochemical course can be dialed in by the proper choice of the alcohol part of the ester and the π-acid. This transformation is compatible with a variety of acid-sensitive groups as witnessed by a number of exigent applications to the total synthesis of natural products, including pseudopyronine A, hispidine, phellinin A, the radininol family, neurymenolide, violapyrone, wailupemycin and an unnamed brominated 4-pyrone of marine origin. Although the reaction proceeds well in neutral medium, the rate is largely increased when HOAc is used as solvent or co-solvent, which is thought to favor the protodeauration of the reactive alkenyl-gold intermediates as the likely rate-determining step of the catalytic cycle. Such intermediates are prone to undergo diauration as an off-cycle event that sequesters the catalyst; this notion is consistent with literature data and supported by the isolation of the gem-diaurated complexes 12 and 15. Furthermore, silver catalysis allowed access to be gained to 2-alkoxypyridine and 2-alkoxyisoquinoline derivatives starting from readily available imidate precursors.

A dramatic substituent effect in silver(I)-catalyzed regioselective cyclization of ortho-alkynylaryl aldehyde oxime derivatives

A dramatic substituent effect was found in the silver(I)-catalyzed cyclization reaction of ortho-alkynylaryl aldehyde oxime derivatives. When R is an alkyl group, the Ag(I)-catalyzed reaction in dimethylacetamide at 110°C (conditions A) affords isoquinoli

A direct anionic cyclization of 2-alkynylbenzonitrile to 3- substituted-1(2H)-isoquinolones and 3-benzylideneisoindol-2ones initiated by methoxide addition

Treatment of 2-(2-alkylethynyl)benzonitrile with sodium methoxide in refluxing methanol for 12 h gave 3-alkyl-1(2H)- isoquinolone in modest yield. Under the same reaction conditions, methanolysis of 2-(2-arylethynyl)benzonitrile lead to the formation of 3

Biphenylmethyl-substituted pyridones

Biphenylmethyl-substituted pyridones are prepared by reaction of pyridones with appropriate biphenylmethyl compounds. The biphenylmethyl-substituted pyridones can be employed as active compounds in medicaments, in particular for the treatment of arter

Sulfonylbenzyl-substituted benzo- and pyridopyridones

Sulfonylbenzyl-substituted benzo- and pyridopyridones are prepared by reacting corresponding benzo- and pyridopyridones with sulphonylbenzyl compounds. The sulphonylbenzyl-substituted benzo- and pyridopyridones can be employed as active compounds in medicaments, in particular for the treatment of arterial hyper tension and atherosclerosis.

O-Methylarenehydroxamates as Ortho-Lithiation Directing Groups. Ti(III)-Mediated Conversion of O-Methyl Hydroxamates to Primary Amides

Reaction of O-methyl benzohydroxamates 2a-c with sec-butyllithium in the presence of TMEDA at -40 deg C regiospecifically generates the highly reactive N,ortho-dilithiated species (e.g. 3).These dilithio species react avidly with a wide spectrum of electrophilic reagents, including alkyl halides, givind adducts which on reduction with TiCl3 are converted into ortho-substituted primary benzamides in excellent yields.Ortho lithiation of O-methyl benzohydroxamates is thus formally equivalent to ortho lithiation of primary benzamides themselves.The utility of these synthetic operations is enhanced by the well-known facility with wich the primary amide moiety can be transformed into other useful functional groups.The conversion of O-methyl hydroxamates to primary amides is shown to be general, as exemplified by transformation of 14a-f to 15a-f.O-Methyl-2-methylbenzohydroxamate (4a) undergoes regiospecific dilithiation on nitrogen and on the methyl group when treated with sec-butyllithium at -70 deg C.These dilithio species react with DMF or "Weinreb-type" amides to give condensation products wich cyclize to N-methoxyisoquinolin-1(2H)-ones under mildly acidic conditions.Removal of the N-methoxy moiety under conditions analogous to those used for O-methyl benzohydroxamate provides N-unsubstituted isoquinolin-1(2H)-ones with high overall efficiency.This process is exemplified by the synthesis of isoquinolin-1(2H)-one 9a, its 3-n-butyl congener 9b, and the tricyclic isoquinolin-1(2H)-ones 20a and 20b from O-methyl 2-methylbenzohydroxamate (4a).

Heteroatom-Directed Metalation. Lithiation of N-Propenylbenzamides and N-Propenyl-o-toluamides. Novel Routes to Ortho-Substituted Primary Benzamide Derivatives and N-Unsubstituted Isoquinolin-1(2H)-ones

Reaction of N-propenylbenzamides 4 and 9, obtained by LDA-induced isomerization of the corresponding N-allylbenzamides, 1, 8, and 14, with 2 equiv of sec-butyllithium or tert-butyllithium at low temperature regiospecifically generates the highly reactive N,ortho-dilithiated species (e.g., 5 and 17).These dilithio species react avidly with a wide spectrum of electophilic reagents, including alky halides, giving adducts which on hydrolysis with warm 50percent aqueous acetic acid are converted into ortho-substituted primary benzamides in excellent yields.Ortho-lithiation of N-propenylbenzamides is thus formally equivalent to ortho-lithiation of primary benzamides themselves.The utility of this important, previously unknown, synthetic operation is enhanced by the well-known facility with which the primary amide moiety can be transformed into other useful functional groups, as exemplified by the synthesis of 2-methoxy-6-methylbenzoic acid (12) and 2-methoxy-6-methylbenzonitrile (13) from N-propenyl-2-methoxybenzamide (9).N-Propenyl-o-toluamide (7) undergoes regiospecific dilithiation on nitrogen and on the methyl group under conditions analogous to those used for the N-propenylbenzamides.These dilithio species react with DMF or "Weinreb type" amides to give condensation products which cyclize to N-propenylisoquinolin-1(2H)-ones under mildly acidic conditions.Removal of the N-propenyl moiety under more strongly acidic conditions provides N-unsubstituted isoquinolin-1(2H)-ones with high overall efficiency.This process is exemplified by the synthesis of isoquinolin-1(2H)-one (23) and its 3-n-butyl congener 26 from N-propenyl-2-methylbenzamide (7).

Substituted 1-(2H)-isoquinolinones bearing acidic functional groups as angiotensin II antagonists

Substituted 1-(2H)-isoquinolinones of the structural formula: STR1 are angiotensin II antagonists which are useful in the treatment of hypertension and congestive heart failure.

Substituted 1-(2H)-Isoquinolinones

Substituted 1-(2H)-isoquinolinones of the structural formula: are angiotensin II antagonists which are useful in the treatment of hypertension and congestive heart failure.