Isatoic Anhydride/4-Dimethylaminopyridine as a Reagent for<i>ortho</i>-Aminobenzoylation

Venuti, Michael C.

doi:10.1055/s-1982-29772

Cited by 30 publications

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“…Our synthetic approach started with the preparation of 2-amino-N-methyl-N-(prop-2-ynyl)benzamide 10a, which was in turn synthesised in a one-step reaction between commercially available isatoic anhydride and N-methylpropargylamine as reported 16 earlier. The reactions of 10a with aryl iodides 8 were carried out under very mild conditions by stirring the mixture at room temperature (27-32 • C) for 2 h in the presence of Pd(PPh 3 ) 2 Cl 2 (4.0 mol%), CuI (6.0 mol%), and triethylamine (7.0 equiv.)…”

Section: Resultsmentioning

confidence: 99%

An expedient and facile route for the general synthesis of 3-aryl substituted 1,2,3-triazolo[1,5-a][1,4]benzodiazepin-6-ones and 1,2,3-triazolo[1,5-a][1,5]benzodiazocin-7-ones

2010

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We describe herein a convenient approach for the general synthesis of novel tricyclic scaffolds incorporating a fusion of the 1,2,3-triazole ring with difficultly obtainable medium sized rings such as [1,4]benzodiazepin-5-ones and [1,5]benzodiazocin-6-ones through Sonogashira coupling of an aryl iodide with 2-amino-N-methyl-N-(prop-2-ynyl)benzamide or homologue followed by in situ diazotisation, azidation and cycloaddition reactions. The strategy also allows easy accessibility of the corresponding amide-reduced analogues. The operational simplicity and easy substrate availability make the process cost effective and practical.

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Section: Resultsmentioning

confidence: 99%

An expedient and facile route for the general synthesis of 3-aryl substituted 1,2,3-triazolo[1,5-a][1,4]benzodiazepin-6-ones and 1,2,3-triazolo[1,5-a][1,5]benzodiazocin-7-ones

2010

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“…Initial studies were directed at developing an experimentally simple and convenient two-step protocol for amide oxidations. It is well known that a secondary amine 13 can be converted in high isolated yield into an o -aminobenzamide derivative 14 using commercially available isatoic anhydride ( 12 ) (Scheme ). In certain cases involving less basic and/or hindered amines an alternative two-step procedure has been used ( vide infra ).…”

Section: Resultsmentioning

confidence: 99%

“…The crude product was purified by flash column chromatography (ethyl acetate/hexanes, 1/1−2/1). Compounds 14a − c and 14f have been previously prepared …”

Section: Methodsmentioning

confidence: 99%

Exploratory Synthetic Studies of the α-Methoxylation of Amides via Cuprous Ion-Promoted Decomposition of o-Diazobenzamides

et al. 1996

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A convenient nonelectrochemical amide oxidation method has been developed. The process involves a cuprous ion-promoted decomposition of o-diazobenzamides like 4, generated in situ from the corresponding o-aminobenzamides, to give N-acyliminium ion intermediate 9 via a 1,5-H-atom transfer, followed by metal-catalyzed oxidation of the resulting α-amidyl radical. The transformation produces α-methoxybenzamides 15 in good yields. An attempt was made to apply this oxidation method to a total synthesis of the alkaloid (−)-anisomycin (16). Scalemic o-aminobenzamide pyrrolidine derivatives 18a/18b underwent oxidation to give α-methoxylated amide substrates 19a/19b, respectively, in good yields. However, alkylation of the N-acyliminium intermediate 20 with (p-methoxybenzyl)magnesium chloride gave the undesired anti-compounds 22a/22b as the major products. The amide oxidation exhibits good regioselectivity with many unsymmetrical 2-substituted piperidine and pyrrolidine systems. In general, it appears that the larger the C-2 substituent, the greater the methylene/methine H-atom abstraction ratio. A mechanistic rationale for this selectivity is suggested based upon amide rotamer populations. An extension of this methodology can be used to conduct two sequential amide oxidations using readily prepared 2-amino-6-nitrobenzamides such as 68 and 69.

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“…Subsequently, Staiger et al [4] investigated the reaction of 3 with a wide variety of nucleophiles and developed the synthesis of esters, diesters, thioesters, amides and ureas. The addition of 4-dimethylaminopyridine (DMAP) as a catalyst can improve the efficiency of the o-aminobenzoylation [5], which can also be affected via active esters of anthranilic acid [6]. These reactions of isatoic anhydride are frequently carried out under conditions of base catalysis; in the absence of a base catalyst, the ring opening reaction affords different products such as the isatoic esters (8) from reaction with alcohols [7].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of a series of 1,x‐bis‐(4‐oxo‐3,4‐dihydro‐1,2,3‐benzotriazin‐3‐yl)alkanes

Hunter

Vaughan

2006

Journal of Heterocyclic Chem

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Reaction of isatoic anhydride with an alkanediamine in DMF solution under mild conditions affords excellent yields of the 1,x‐bis‐{(2‐aminobenzoyl‐)amino}alkanes (2a‐k), which have been characterized by IR and NMR spectroscopy, high resolution mass spectrometry and elemental analysis. Diazotization of the bis‐{(2‐aminobenzoyl‐)‐amino}alkanes in aqueous solution gives high yields of the 1,x‐bis‐(4‐oxo‐3,4‐dihydro‐1,2,3‐benzotriazin‐3‐yl)alkanes (1a‐k), whch have also been characterized by IR and NMR spectroscopy, high resolution mass spectrometry and elemental analysis. The alkanediamines employed are as follows: ethylene diamine, 1,3‐propanediamine, 1,2‐propanediamine, 2‐methyl‐1,2‐propanediamine, 2,2‐dimethyl‐1,3‐propanediamine, 2‐hydroxy‐1,3‐propanediamine, 1,4‐diaminobutane, 1,5‐diaminopentane, 1,3‐diaminopentane (DYTEK® EP diamine), 1,6‐diaminohexane and 1,7‐diaminoheptane. The alternative method of synthesis of the bis‐(4‐oxo‐3,4‐dihydro‐1,2,3‐benzotriazin‐3‐yl)alkanes (1) via the diazonium salt from methyl anthranilate was explored.

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Isatoic Anhydride/4-Dimethylaminopyridine as a Reagent forortho-Aminobenzoylation

Cited by 30 publications

References 0 publications

An expedient and facile route for the general synthesis of 3-aryl substituted 1,2,3-triazolo[1,5-a][1,4]benzodiazepin-6-ones and 1,2,3-triazolo[1,5-a][1,5]benzodiazocin-7-ones

An expedient and facile route for the general synthesis of 3-aryl substituted 1,2,3-triazolo[1,5-a][1,4]benzodiazepin-6-ones and 1,2,3-triazolo[1,5-a][1,5]benzodiazocin-7-ones

Exploratory Synthetic Studies of the α-Methoxylation of Amides via Cuprous Ion-Promoted Decomposition of o-Diazobenzamides

Synthesis and characterization of a series of 1,x‐bis‐(4‐oxo‐3,4‐dihydro‐1,2,3‐benzotriazin‐3‐yl)alkanes

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