Reissert Compounds Research Articles

ChemInform Abstract: Regioselectivity in the Alkylation of Ambident Anions of 1‐Acyl‐1,2‐dihydroquinaldonitriles (Quinoline Reissert Compounds).

AbstractAlkylation of N‐benzoyl‐4‐methyl‐1,2‐dihydroquinaldonitrile (I) with methyl iodide (II) produces the dimethyldihydroquinaldonitriles (III) and (IV).

Reaction of reissert anion with aldimines: A new approach to the imidazo[5,1‐α]isoquinoline ring system

AbstractThe carbanion derived from N‐alkoxycarbonyl Reissert compound readily undergoes addition‐cyclization reaction with aldimines to give imidazo[5,1‐a]isoquinolines. A detailed study of this new ring annelation chemistry is described.

Polymers from Reissert compounds. 3. Polyesters from reactions of dialdehydes with Reissert compounds derived from bis(isoquinolines)

Le traitement de la decamethylenedioxydiphenyldimethylene bis-isoquinoleine par le chlorure de benzoyle et le cyanure de trimethylsilyle donne le compose de Reissert correspondant. La reaction du dianion de ce compose avec le decamethylenedioxy-bis-benzaldehyde donne des polymeres comportant des motifs isoquinoleine, des motifs ethers et des groupes lateraux arylates

ChemInform Abstract: Studies on Pyrazolo(3,4‐d)pyrimidine Derivatives. Part 17. Reactions of 5‐Benzoyl‐4,5‐dihydro‐6‐methyl‐1‐phenyl‐1H‐pyrazolo(3,4‐d)pyrimidine‐4‐carbonitrile (The 6‐Methylpyrazolopyrimidine Reissert Compound).

AbstractAcidic hydrolysis of the title compound (I) gives the ring‐cleaved pyrazole (II) and the pyrazolyloxazole (III), whereas alkaline hydrolysis of (I) forms the pyrazolopyrimidine (IV).

Réaction du fluoroborate de 2-benzoyl-1,2-dihydro isoquinaldonitrile avec les esters α,β-éthyléniques. II. Cas des esters oléfiniques gem-disubstitués. Stéréochimie des produits de condensation–réarrangement, dérivés du 4,5-dihydro-3H-pyrrole

The previously suggested mechanism of the condensation–rearrangement reaction of a Reissert compound hydrofluoroborate salt with reactive olefins was reexamined in the case of methyl methacrylate, itaconate, citraconate, and mesaconate. Addition of triethylamine to the reaction medium leads to the isolation of a presumed intermediate 8. Spectrometric (proton magnetic resonance) data of the compounds 8 allow us to specify their stereochemistry and in two cases to point out an isomerization equilibrium. Keywords: Reissert compound fluoroborate salt, [4 + 2] cycloaddition, stereochemistry.

Regioselectivity in the alkylation of ambident anions of 1-acyl-1,2-dihydroquinaldonitriles (quinoline Reissert compounds)

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTRegioselectivity in the alkylation of ambident anions of 1-acyl-1,2-dihydroquinaldonitriles (quinoline Reissert compounds)Harry W. Gibson and Bardia GuilaniCite this: J. Org. Chem. 1990, 55, 13, 4226–4229Publication Date (Print):June 1, 1990Publication History Published online1 May 2002Published inissue 1 June 1990https://doi.org/10.1021/jo00300a056RIGHTS & PERMISSIONSArticle Views98Altmetric-Citations7LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (581 KB) Get e-Alerts Get e-Alerts

ChemInform Abstract: Reissert Compound Formation by Use of Solid‐Liquid Phase‐Transfer Catalysis.

AbstractThe reported method is effective with both five‐ and six‐membered ring N‐heterocycles except benzothiazole giving only low yields of Reissert compounds.

ChemInform Abstract: Reissert Compound Formation with Fused Five‐Membered Ring Heterocycles.

AbstractA variety of new Reissert compounds such as (IV), derived from benzoxazole and benzothiazole, is prepared by use of trimethylsilyl cyanide (II) as a source of cyanide in a single‐phase system.

ChemInform Abstract: Reissert Compound Studies. Part 61. Preparation and Reactions of Quinazoline Di‐Reissert Compounds.

AbstractNine title compounds of type (IV) are prepared and their reactions are compared with those of corresponding mono‐Reissert compounds.

ChemInform Abstract: Benzologous Reissert Compound Formation from 2‐Methylindazole.

Abstract2‐Methylindazole (I) is treated with trimethylsilyl cyanide (II) and benzoyl chloride (IIIa) or the chloroformates (IIIb) and (IIIc) to produce the acyldihydroindazolecarbonitriles (IV).

Studies on pyrazolo(3,4-d)pyrimidine derivatives. XVII. Reactions of 5-benzoyl-4,5-dihydro-6-methyl-1-phenyl-1H-pyrazolo(3,4-d)pyrimidine-4-carbonitrile (The 6-methylpyrazolopyrimidine Reissert compound).

Acid hydrolysis of the 6-methylpyrazolopyrimidine Reissert compound (6) gave the ring-opened product (12) and the oxazole (13). Alkaline hydrolysis of 6 afforded the 6-methylpyrazolopyrimidine (7) and benzoic acid (15). The anion (1) of 6 mainly underwent both aromatization and rearrangement, resulting in the formation of the 6-methylpyrazolopyrimidinecarbonitrile (20) and the 4-benzoyl-6-methylpyrazolopyrimidine (21) together with by-products such as 7, the dimer (22), the benzoate (23a), and O-benzoylbenzoin (24a). The anion I added to the carbonyl carbon of aromatic aldehydes (8a-c), giving the benzoates (23a-c) together with 7, the O-benzoylaroins (24a-c), and the O-benzoylcyanohydrins (27a, c).

ChemInform Abstract: Reissert Compound Studies. Part 110. Heterogeneous Synthesis of Reissert Compounds Utilizing Potassium Cyanide Adsorbed on Amberlite XAD Resins.

ChemInform Abstract: Reissert Compound Studies. Part 110. Heterogeneous Synthesis of Reissert Compounds Utilizing Potassium Cyanide Adsorbed on Amberlite XAD Resins.

ChemInform Abstract: Novel Tricyclic Heterocycles (Benzopyrrocolines) Arising via Carbanion Attack on a Nitrile Function.

AbstractAlkylation of the isoquinoline Reissert compounds (I) leads directly to the benzopyrrocoline derivatives (III) and (IV); the NMR spectra reveal a solvent‐dependent tautomeric equilibrium between both forms.

ChemInform Abstract: Purines. Part 8. Reactions of 1‐Benzoyl‐1,6‐dihydro‐9‐phenyl‐9H‐purine‐6‐carbonitrile (9‐Phenylpurine Reissert Compound) with Acid, Bases, and Electrophiles.

AbstractAcidic hydrolysis of the title compound (I) leads to the formation of the ring fission products (II) and (III), whereas alkaline hydrolysis of (I) yields 9‐phenyl‐9H‐purine (IV) and benzoic acid (V).

Reissert Compound Studies. LXI. Preparation and Reactions of Quinazoline Di‐Reissert Compounds

AbstractVarious di‐Reissert compounds and analogs were prepared from quinazoline by use of trimethylsilyl cyanide together with a catalytic amount of anhydrous aluminum chloride. Reactions of these quinazoline di‐Reissert compounds are reported.

ChemInform Abstract: Syntheses of the Benzylisoquinoline Alkaloids Isosevanine and Berbithine

The benzylisoquinoline alkaloids isosevanine (1) and berbithine (2) have been synthesized by alkylation of the Reissert compound (5), derived from 6,7-methylenedioxyisoquinoline, with the appropriate benzyl chlorides (6) and (7) respectively followed by hy drogenolysis of the protecting group.

ChemInform Abstract: Preparation of Oxazolo(4,3‐a)phthalazin‐3‐ones by Use of Reissert Compounds.

AbstractThe Reissert nitrile (I) (prepared in 80% yield from phthalazine, Me3SiCN, and Ph‐CO‐Cl in the presence of AlCl3) is transformed to its conjugate base and then condensed with aldehydes (II) to give, after hydrolysis, the methanols (IV).

Benzologous Reissert Compound Formation from 2-Methylindazole

Abstract 2-Methylindazole undergoes 1, 4-addition on treatment under Reissert conditions. Methylation of the product in strong base leads to 2, 3-dimethylindazole.

ChemInform Abstract: Organic Sonochemistry. Synthesis, and Use of Reissert Compounds Under PTC‐Ultrasound.

AbstractThe isoquinoline Reissert compound (I) reacts with the benzyl chlorides (II) in the presence of a phase transfer catalyst under ultrasonication to form the substitution products (III) which are hydrolyzed to yield the isoquinolines (IV).

Novel tricyclic heterocycles (benzopyrrocolines) arising via carbanion attack on a nitrile function

AbstractA new reaction of 2‐n‐alkanoyl‐1,2‐dihydroisoquinaldonitriles 1 (isoquinoline Reissert compounds) has been discovered. As previously reported reaction of the conjugate bases of Reissert compounds with alkyl halides yields the corresponding 1‐alkyl derivatives 2. However, compounds 2, R = n‐alkyl, with only a catalytic amount of bases form the enolate ion, which attacks the neighboring nitrile functionality to produce directly in the same reaction vessel excellent yields of benzopyrrocoline derivatives 5‐10. The nmr spectrum reveals a solvent dependent tautomeric equilibrium between ketoeneamine (a) and ketoimine (b) forms. Unlike compounds 2 the double bonds of the pyridine ring of compounds 7 and 8 were readily reduced with hydrogen. Thus, n‐alkanoyl Reissert compounds afford a convenient route to the corresponding benzopyrroco‐lines.