Copper(I)-induced addition of amines to unactivated nitriles: The first general one-step synthesis of alkyl amidines.

Rousselet, Guilhem; Capdevielle, Patrice; Maumy, Michel

doi:10.1016/0040-4039(93)85054-z

Cited by 126 publications

(64 citation statements)

References 7 publications

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“…No reaction occurred in the absence of thiophilic reagents up to a temperature of 1108. An attempt to transform the carbonitriles 15, 17, and 26 to amidines by aminolysis of the corresponding nitrilium salts, generated under conditions of the Pinner reaction [43] or in the presence of a Lewis acid [44] [45], and further to imidazoles also failed, as did the formation of an imidazole ring from the amides 21 or 24.…”

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confidence: 99%

Synthesis of Fusion‐Isomeric Imidazopyridines and Their Evaluation as Inhibitors of syn‐ and anti‐Protonating Glycosidases

Mohal

Vasella

2005

Helvetica Chimica Acta

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The galacto-and gluco-configured imidazopyridines 4 and 5 were synthesised as potential inhibitors of synprotonating b-glycosidases. Methyl a-d-lyxopyranoside (9) was transformed into the 3,4-anhydro-b-l-riboside 16, which, upon treatment with Et 2 AlCN, gave the nitrile 17 (76 ± 85%). Reaction of 17 with the dimethyl aluminate of aminoacetaldehyde dimethyl acetal led directly to the branched chain lyxo-configured imidazole 27 (53%) that was hydrolysed to an equilibrating mixture of 4 and 28 ± 30. Oxido reduction of 27 provided the arabino-configured imidazole 42 (ca. 48% from 27). Hydrolysis of 42 led to the mixture 5/45 (63 ± 90%). antiProtonating b-galactosidases and b-glucosidases (families 1 and 2) were only weakly inhibited by 4/28 ± 30 and 5/ 45, respectively. Also the syn-protonating cellulase (Cel7A) was weakly inhibited by the monosaccharide mimics 5/45, suggesting either that monosaccharide mimics are too small to inhibit Cel7A, or that fusion isomeric tetrahydroimidazo[1,2-a]pyridines are not a suitable scaffold for the inhibition of syn-protonating glycosidases.Introduction. ± Selective inhibitors of anti-and syn-protonating glycosidases [1] will be useful to specify the (relative) position of the catalytic acid; they also have the potential of being highly selective. Of particular interest are complementary inhibitors of syn-and anti-protonating glycosidases possessing a common scaffold, as this would facilitate a comparative interpretation of the inhibitory activity. However, there are as yet no inhibitors selective for syn-protonating (a-or b-) glycosidases.The anti-and syn-protonating glycosidases differ by the trajectory of the proton transfer from the catalytic acid AH to the glycosidic oxygen (I and II) and the tetrahydroimidazo[1,2-a]pyridines of type 1 are strong (about nanomolar) inhibitors of

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confidence: 99%

Synthesis of Fusion‐Isomeric Imidazopyridines and Their Evaluation as Inhibitors of syn‐ and anti‐Protonating Glycosidases

Mohal

Vasella

2005

Helvetica Chimica Acta

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“…Um procedimento experimental capaz de obter exclusivamente amidinas monossubstituídas é o emprego de uma razão molar 1;1,2 (amina/CuCl). Quando utilizaram piridina como solvente a reação não ocorreu 41 (Esquema 6).…”

Section: Esquema 3 Estrutura Da Distamicina Dos Santos Et Alunclassified

Principais métodos de síntese de amidinas

Santos¹,

Bernardino²,

Souza³

2006

Quím. Nova

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Recebido em 8/6/05; aceito em 6/1/06; publicado na web em 6/7/06 SYNTHETIC APPROACHES TO AMIDINES. The amidine functional group is found in a wide range of natural products and is biologically active against several pathogens. In addition, amidines have long been regarded as useful intermediates in the synthesis of heterocyclic compounds. Consequently, a great number of methods have been developed for the preparation of amidines. Pinner's method is the most commonly used. Conventional methods include: -the addition of metal amides or amines to nitriles, the addition of amines to imido esters and the condensation of amides with amines in the presence of halogenating reagents. In this report, the main methods for synthesis of amidines will be described.

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“…19 Stoichiometric copper(I) chloride induced addition of various amines to nitriles provided amidines in excellent yields (Scheme 7).…”

Section: Methodsmentioning

confidence: 99%

Functionality of amidines and amidrazones

Aly¹,

El‐Din²

2008

Arkivoc

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Copper(I)-induced addition of amines to unactivated nitriles: The first general one-step synthesis of alkyl amidines.

Cited by 126 publications

References 7 publications

Synthesis of Fusion‐Isomeric Imidazopyridines and Their Evaluation as Inhibitors of syn‐ and anti‐Protonating Glycosidases

Synthesis of Fusion‐Isomeric Imidazopyridines and Their Evaluation as Inhibitors of syn‐ and anti‐Protonating Glycosidases

Principais métodos de síntese de amidinas

Functionality of amidines and amidrazones

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