The use of ω-iodoazides as primary protected electrophilic reagents. Alkylation of some carbanions derived from active methylene compounds and N,N-dimethylhydrazones

Khoukhi, M.; Vaultier, Michel; Carrié, R.

doi:10.1016/s0040-4039(86)80040-5

Cited by 41 publications

(23 citation statements)

References 10 publications

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“…The product of this reaction was not isolated due to its possible explosive character, but was directly subjected to the tosylation to yield 23 [ 31 ]. Finally, compound 24 was prepared by means of the Finkelstein reaction (which was already published [ 32 ]) in 96% yield.…”

Section: Resultsmentioning

confidence: 99%

A complete series of 6-deoxy-monosubstituted tetraalkylammonium derivatives of α-, β-, and γ-cyclodextrin with 1, 2, and 3 permanent positive charges

Popr¹,

Hybelbauerová²,

Jindřich³

2014

Beilstein J. Org. Chem.

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SummaryAn efficient synthetic route toward the preparation of a complete series of monosubstituted tetraalkylammonium cyclodextrin (CD) derivatives is presented. Monotosylation of native CDs (α-, β-, γ-) at position 6 gave the starting material. Reaction of monotosylate (mono-Ts-CD) with 45% aqueous trimethylamine gave CDs substituted with one cationic functional group in a single step. Derivatives equipped with a substituent containing two cationic sites separated by an ethylene or a propylene linker were prepared by reacting mono-Ts-CD with neat N,N,N’-trimethylethane-1,2-diamine or N,N,N’-trimethylpropane-1,3-diamine and subsequent methylation by CH3I in good yields. Finally, analogues bearing a moiety with three tetraalkylammonium sites were synthesized by reacting mono-Ts-CD with bis(3-aminopropyl)amine and subsequent methylation. The majority of the presented reactions are very straightforward with a simple work-up, which avoids the need of chromatographic separation. Thus, these reactions are suitable for the multigram-scale production of monosubstituted cationic CDs.

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Section: Resultsmentioning

confidence: 99%

A complete series of 6-deoxy-monosubstituted tetraalkylammonium derivatives of α-, β-, and γ-cyclodextrin with 1, 2, and 3 permanent positive charges

Popr¹,

Hybelbauerová²,

Jindřich³

2014

Beilstein J. Org. Chem.

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“…Accordingly, the treatment of ester 11 with LHMDS and addition of the three‐carbon‐atom iodo azide 12 delivered the expected product 13 in high yield. In contrast, in the analogous reaction of 11 with the two‐carbon‐atom iodo azide 14 , the desired azido ester 15 was not observed. Instead, the unexpected N ‐vinyl amide 16 was isolated in 85 % yield.…”

Section: Methodsmentioning

confidence: 87%

Unexpected Direct Synthesis of N‐Vinyl Amides through Vinyl Azide–Enolate [3+2] Cycloaddition

Choi,

Shirley,

Hume

et al. 2017

Angew Chem Int Ed

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The unexpected synthesis of industrially important N-vinyl amides directly from aldehydes and α,β-unsaturated N-vinyl amides from esters is reported. This reaction probably proceeds through an initial [3+2] azide-enolate cycloaddition involving a vinyl azide generated in situ. A survey of the reaction scope and preliminary mechanistic findings supported by quantum computational analysis are reported, with implications for the future development of atom-efficient amide synthesis. Intriguingly, this study suggests that (cautious) reevaluation of azidoethene as a synthetic reagent may be warranted.

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“…Ketoazide 70 was identified as a suitable target. The desired substrate was readily prepared by elaboration of trans-decalone 68 into the desired ketoazide using methodology developed by Vaultier and coworkers, 17 who have previously demonstrated that carbanions derived from N,N-dimethylhydrazones 18 can be alkylated with b-iodoazides (Scheme 8). The iodoazide 67, required for the subsequent alkylation step, was prepared in three steps: the azido alcohol 65 was formed by reaction of 2-chloroethanol (64) and NaN 3 in DMF.…”

Section: Methodsmentioning

confidence: 99%

The 2-(2-Azidoethyl)cycloalkanone Strategy for Bridged Amides and Medium-Sized Cyclic Amine Derivatives in the Aubé-Schmidt Reaction

Macleod¹,

Lang

Murphy

2010

Synlett

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The use of ω-iodoazides as primary protected electrophilic reagents. Alkylation of some carbanions derived from active methylene compounds and N,N-dimethylhydrazones

Cited by 41 publications

References 10 publications

A complete series of 6-deoxy-monosubstituted tetraalkylammonium derivatives of α-, β-, and γ-cyclodextrin with 1, 2, and 3 permanent positive charges

A complete series of 6-deoxy-monosubstituted tetraalkylammonium derivatives of α-, β-, and γ-cyclodextrin with 1, 2, and 3 permanent positive charges

Unexpected Direct Synthesis of N‐Vinyl Amides through Vinyl Azide–Enolate [3+2] Cycloaddition

The 2-(2-Azidoethyl)cycloalkanone Strategy for Bridged Amides and Medium-Sized Cyclic Amine Derivatives in the Aubé-Schmidt Reaction

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