Chemistry of hydrazides. X. The reduction of cyclic and acyclic hydrazides with diborane

Feuer, Henry; Brown, Frank

doi:10.1021/jo00830a045

Cited by 52 publications

(25 citation statements)

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“…The reduction by active metals (Aeberli and Houlihan 1969) or boron compounds (Feuer and Brown 1970), hydrogenation on platinum group metals (Stetter and Findeisen 1965), and application of hydrazine hydrate on Raney nickel (Robinson and Brown 1961) should be mentioned as the most widely used methods. A number of chiral compounds, for example, c-amino alcohols, or some other bifunctional compounds (Tufariello 1979;Kozikowski and Chen 1981;Kozikowski and Adamczyk 1983) have been obtained via N-O bond breaking in chiral isoxazolines and isoxazolidines.…”

Section: Resultsmentioning

confidence: 99%

“…The convenient way of synthesis of the starting compounds in diasteriomerically pure forms had been developed by us earlier (Sviridova et al 2008;Tavtorkin et al 2009). All aforementioned reductive methods were tested for the preparation of polyamines; however, the satisfactory results were obtained only for the borane-tetrahydrofuran complex (Feuer and Brown 1970;Enders et al 1998Enders et al , 1999. This reagent not only reduced N-acetyl group, but also splitted N-N bond in a heterocycle, giving rise to polyamines in the form of boron-containing complexes.…”

Section: Resultsmentioning

confidence: 99%

“…The idea of the socalled semisynthetic approach (Weisell et al 2010) implies further modification of functional groups of natural compounds not affecting carbon skeletons (usually sugars), but in such cases it is difficult to obtain enantiomers that do not exist in nature. A number of methods for the synthesis of diamines (Robinson and Brown 1961;Stetter and Findeisen 1965;Aeberli and Houlihan 1969;Feuer and Brown 1970) have been reported. However, the general approach to the synthesis of chiral amino compounds with three or more functional groups has been still undeveloped.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of hydroxydiamines and triamines via reductive cleavage of N–N bond in substituted pyrazolidines

et al. 2012

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Aliphatic polyamines, being a versatile class of organic compounds, are widely used in many fields of medicine and organic chemistry. However, the general approach to the synthesis of chiral aliphatic polyamines has been still undeveloped. Here, we describe a new method for the synthesis of chiral trifunctional amino compounds, namely hydroxydiamines and triamines. The initial compounds, namely substituted hydroxy- or aminopyrazolidines and pyrazolines, are readily available using convenient stereoselective methods developed earlier by us. The proposed method allows synthesizing of chiral diaminoalcohols and triamines, which are the analogs of a well-known anti-TB drug, namely ethambutol, and cannot be obtained alternatively. The key step of the synthesis is N-N bond cleavage in substituted hydroxy- or aminopyrazolidines and pyrazolines with borane-tetrahydrofuran complex; other known methods for N-N bond cleavage turned out to be ineffective. The main advantage of the proposed method is the retention of a certain configuration of stereocenters in the course of the reaction. Six new chiral diasteomerically pure substituted hydroxydiamines and triamines and the enantiomerically pure triamine with four chiral centers were synthesized and characterized using NMR, IR and mass spectroscopy, as well as elemental analysis.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis of hydroxydiamines and triamines via reductive cleavage of N–N bond in substituted pyrazolidines

et al. 2012

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“…[45] This method has been reliable in application to our N-acylhydrazine (hydrazide) radical adducts, but it requires a large excess of borane and long reaction times in refluxing THF. For those targets which do not present functional group incompatibility with these conditions, borane reduction is effective.…”

Section: N-n Cleavage With Boranementioning

confidence: 99%

Chiral N‐Acylhydrazones: Versatile Imino Acceptors for Asymmetric Amine Synthesis

Friestad

2005

Eur J Org Chem

122

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Addition to C=N bonds with acyclic stereocontrol offers excellent potential for development of new carbon-carbon bond construction approaches to chiral amines. This review features the design and implementation of novel chiral Nacylhydrazones as versatile imino acceptors for addition of radicals and nucleophiles. The initial design was inspired by the goal of asymmetric radical addition to chiral C=N radical acceptors. The chiral N-acylhydrazones are prepared from commercially available materials by amination of 4-alkyl-2-oxazolidinones with NH 2 + equivalents to afford N-(amino) oxazolidinones, followed by condensation with aldehydes or ketones. These chiral N-acylhydrazones undergo addition reactions with various partners, including radicals, allylsilanes, allylindiums, silyl enol ethers, and hydride donors. The MICROREVIEWS: This feature introduces the readers to the authors' research through a concise overview of the selected topic. Reference to important work from others in the field is included.

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“…1 Among various methods for the synthesis of amines, hydrazines often appear as key intermediates. [2][3][4][5][6][7][8][9][10][11][12] Remarkable examples are the addition of alkylzinc reagent to arylazo tosylates, 12 electrophilic addition of -diazoesters with ketones, 13 the addition of carbon nucleophiles to azodicarboxylates 14 and acylhydrazonium salts, 15 the anionic 8,16 or radical 17 additions to the C=N bond of hydrazones, the cross-coupling of ketones with hydrazones, 18 the addition of N-aminolactams to Michael acceptors, 10,19 the aza-Michael addition of hydrazines to electrophilic alkenes, 20 the radical cyclization of N-allyl--perchlorohydrazides, 21 and the 1,3-dipolar cycloaddition of azomethine imines to dipolarophiles. 22 These examples clearly show the significance of N,N bond cleavage in organic synthesis.…”

Section: Introductionmentioning

confidence: 99%

Reduction of hydrazines to amines with low-valent titanium reagent

Ren¹,

Zhang²,

Hu³

et al. 2013

Arkivoc

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The N,N bond cleavage in hydrazines to amines via low-valent titanium reagent prepared in situ by treatment of TiCl4 with Mg powder in THF or CH2Cl2-Et2O is described. The reaction proceeds smoothly under mild conditions to afford amines in good to excellent yields with diverse functional group tolerance such as chloride, methoxyl, benzyloxyl, ester, acyl, as well as C,C double bonds and benzyl-nitrogen bonds.

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Chemistry of hydrazides. X. The reduction of cyclic and acyclic hydrazides with diborane

Cited by 52 publications

References 0 publications

Synthesis of hydroxydiamines and triamines via reductive cleavage of N–N bond in substituted pyrazolidines

Synthesis of hydroxydiamines and triamines via reductive cleavage of N–N bond in substituted pyrazolidines

Chiral N‐Acylhydrazones: Versatile Imino Acceptors for Asymmetric Amine Synthesis

Reduction of hydrazines to amines with low-valent titanium reagent

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