5-(2,4,6-trinitrophenyl)furfural

Ivonin, S. P.; Anishchenko, A. A.; Voevudskii, M. V.; Dmitrikova, L. V.

doi:10.1007/bf02251557

Cited by 4 publications

(3 citation statements)

References 3 publications

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“…However, to date, this reaction has only been performed with the vinylogous azaenamine furan-2-carbaldehyde dimethylhydrazone [53] and not with the formaldehyde hydrazone itself (Scheme 16).…”

Section: Reactions Of Formaldehyde Dialkylhydrazones With Some Other mentioning

confidence: 99%

Aldehyde N,N‐Dialkylhydrazones as Neutral Acyl Anion Equivalents: Umpolung of the Imine Reactivity

et al. 2007

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The isoelectronic replacement of the α‐carbon of enamines by nitrogen leads to the corresponding hydrazones, and thus, they can be termed “aza‐enamines”. Hence, aldehyde N,N‐dialkylhydrazones enable analogous electrophilic substitutions at the imine carbon that corresponds to the β‐carbon of enamines. In addition, after hydrolysis of the product hydrazones to the parent ketones or aldehydes, these reactions constitute an umpolung of the classical carbonyl reactivity and overall a nucleophilic acylation or formylation. This review covers the aza‐enamine chemistry from its very beginning in the late 1960s up to this year. In the first part, reactions of aromatic, aliphatic, and heterocyclic aldehyde N,N‐dialkylhydrazones with highly reactive substrates such as the Vilsmeier and Mannich reagents, sulfonyl isocyanates, perfluoroacetic anhydride, and inorganic electrophiles such as halogens and phosphorus tribromide are described. The hydrazones of α,β‐unsaturated aldehydes react as vinylogous aza‐enamines at the terminal carbon providing unsaturated aldehydes. As electron‐rich dienes and dienophiles, they also form Diels–Alder adducts and thus interesting N‐heterocycles. The second part covers carbon–carbon bond formations of the sterically less‐demanding formaldehyde N,N‐dialkylhydrazones with synthetically very useful electrophiles such as various Michael acceptors and carbonyl compounds. Formaldehyde SAMP‐hydrazone and related derivatives generally give excellent asymmetric inductions. Finally, first organocatalytic versions of the aza‐enamine chemistry are presented. In summary, the rich chemistry of aldehyde N,N‐dialkylhydrazones as neutral acyl anion, formyl anion, and cyanide equivalents is demonstrated. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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Section: Reactions Of Formaldehyde Dialkylhydrazones With Some Other mentioning

confidence: 99%

Aldehyde N,N‐Dialkylhydrazones as Neutral Acyl Anion Equivalents: Umpolung of the Imine Reactivity

et al. 2007

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“…2-Furaldehyde dimethylhydrazone (2FDH; also known as furfural N,N-dimethylhydrazone, 2-furancarbaldehyde dimethylhydrazone, furan-2-carbaldehyde dimethylhydrazone or 2-furaldehyde 2,2-dimethylhydrazone) is a dimethylamino substituted hydrazone where the C atom is linked to a 2-furyl moiety. It can be synthesized from furfural and unsym-dimethylhydrazone [7], being mainly used in the chemical synthesis of furaldehyde derivatives [8] and many biologically active molecules relevant to the pharmaceutical industry, including trinitrophenyl, furylquinones and hydroquinones [9,10].…”

Section: Introductionmentioning

confidence: 99%

Structure and UV-induced photochemistry of 2-furaldehyde dimethylhydrazone isolated in rare gas matrices

Araujo-Andrade

Giuliano

Gómez‐Zavaglia

et al. 2012

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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“…We attribute a certain degree of regioselectivity to the fact that the highly electron-donating (dialkylhydrazono)methyl group is efficiently conjugated with the ring, thus activating it to a sufficient degree to enable phosphorylation [9] and trinitrophenylation [10] (i.e., electrophilic substitutions with low-reactivity electrophiles). …”

Section: Introductionmentioning

confidence: 99%

Mutual Influence of (Dimethylhydrazono)methyl Groups and α‐Hydroxy Ketone Moieties in Hetaryl Analogues of Unsymmetric Benzoins

et al. 2004

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5-(2,4,6-trinitrophenyl)furfural

Cited by 4 publications

References 3 publications

Aldehyde N,N‐Dialkylhydrazones as Neutral Acyl Anion Equivalents: Umpolung of the Imine Reactivity

Aldehyde N,N‐Dialkylhydrazones as Neutral Acyl Anion Equivalents: Umpolung of the Imine Reactivity

Structure and UV-induced photochemistry of 2-furaldehyde dimethylhydrazone isolated in rare gas matrices

Mutual Influence of (Dimethylhydrazono)methyl Groups and α‐Hydroxy Ketone Moieties in Hetaryl Analogues of Unsymmetric Benzoins

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