Synthesis Of Isoquinoline Derivatives Research Articles

Utility of Activated Nitriles in the Synthesis of Isoquinoline Derivatives

γ-Cyano-γ-(4-pyridyl) pimelonitrile (2) has been prepared by cyanoethylation of 4-pyridyl-acetonitrile (1). Hydrolysis of (2) using dil. HCl afford γ- amido-γ-(4-pyridyl) pimelic acid (3) which cyclized to the corresponding 3-(4-pyridyl)-2, 6-piperidindione-3-propionic acid (4) by continuos heating in hydrochloric acid solution. Ring closure of (4) takes place in the presence of conc. sulphuric acid to give spiroisoquinoline derivative (5). Spiroisoquinoline derivatives (8) - (11) have been also prepared. Structure of all the products have been established by elemental and spectral analyses.

Synthesis of isoquinoline derivatives by Diels-Alder reactions of 2(1H)-pyridones having an electron-withdrawing group with methoxy-1,3-butadienes.

Diels-Alder (DA) reactions of 2(1H)-pyridones having an electron-withdrawing group at the 4-position with 2,3-dimethoxy- and 2-methoxy-1,3-butadienes gave isoquinoline derivatives. Furthermore, an isoquinoline alkaloid (6,7-dimethoxy-2-methyl-1(2H)-isoquinolone) was synthesized by elimination of hydrogen cyanide and dehydrogenation of the DA-adduct having a cyano group at the 4a-position.

ChemInform Abstract: A New Easy One‐Step Synthesis of Isoquinoline Derivatives from Substituted Phenylacetic Acid.

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Inverse-electron-demand diels-alder reactions of condensed pyridazines, part 2. Synthesis of isoquinoline derivatives from pyrido[3,4- d]pyridazines.

Employment of pyrido[3,4- d]pyridazine derivatives 1, 2, 3 as aza-dienes in inverse-electron-demand Diels-Alder reactions with 1-pyrrolidino-1-cyclopentene or its six-membered homologue, respectively, was found to provide an easy access to the isoquinolines 5, 7, 9, 11, 13, 15 after aromatisation of intermediate mixtures of regioisomeric dihydroisoquinoline derivatives.

Synthesis of isoquinoline derivatives by a tandem aza-Wittig/electrocyclization strategy and preparation of the unknown 1,9-diazaphenalene ring by a consecutive electrocyclic ring closure/Claisen rearrangement/intramolecular amination process

Treatment of iminophosphrane 3, derived from ethyl α-azido-2-(allyloxy) cinnamate, with aromatic isocyanates in toluene at 150 o C leads to the corresponding isoquinoline derivatives 5 by a tandem electrocyclic ring closure/Claisen rearrangement of the intermediate carbodiimide. Fremy's salt promoted oxidation of compounds 5 yields the 5,8-isoquinolinequinone allides 6, which by heating undergo cyclization to 2H-pyrano [2,3-f] isoquinolines isocyanates to give the corresponding carbodiimides, which by thermal treatment at 150 o C undergo a consecutive electrocyclic ring closure/Claisen rearrangement/intramolecular amination process to give 1,9-diazaphenalene derivatives

ChemInform Abstract: Preparation and Thermal Ring Closure of β‐Arylvinylcarbodiimides: Synthesis of Isoquinoline Derivatives.

ChemInform Abstract: Preparation and Thermal Ring Closure of β‐Arylvinylcarbodiimides: Synthesis of Isoquinoline Derivatives.

Preparation and thermal ring-closure of β-aryl vinyl carbodi-imides: synthesis of isoquinoline derivatives

Reaction of the iminophosphoranes (7)–(9), derived from α-azidocinnamates and tri-phenylphosphine, with aromatic isocyanates gives either 1-arylaminoisoquinoline-3-carboxylates (10)–(12) or the corresponding carbodi-imides (14)–(18) which by thermal treatment at 230 °C are converted into 1-(N-aryl-N-imidazolylamino)isoquinoline-3-carboxylates (19)–(20). The iminophosphoranes (7) and (8) also react with aroyl chlorides to give the oxazolone derivatives (23)–(26).

Diels-Alder Reaction of 1-Methyl-4-substituted 2(1H)-Pyridones with Alkyl-1,3-butadiene. A Novel Synthesis of Isoquinoline Derivatives

Diels-Alder Reaction of 1-Methyl-4-substituted 2(1H)-Pyridones with Alkyl-1,3-butadiene. A Novel Synthesis of Isoquinoline Derivatives

A Novel Synthesis of Isoquinoline Derivatives

A Novel Synthesis of Isoquinoline Derivatives

Studies on the Syntheses of Heterocyclic Compounds. CCCXXI. Synthesis of Isoquinoline Derivatives having Twenty-four Membered Ring System by Ullmann Reaction

Studies on the Syntheses of Heterocyclic Compounds. CCCXXI. Synthesis of Isoquinoline Derivatives having Twenty-four Membered Ring System by Ullmann Reaction

Studies on tetrahydroisoquinolines (THI). I. Bronchodilator activity and structure-activity relationship.

For many years the synthesis of isoquinoline derivatives has been carried out in our Organic Chemistry Research Laboratory. In the process of pharmacological screening tests, 1-(3, 4-dihydroxybenzyl)-6, 7-dihydroxy-1, 2, 3, 4-tetrahydroisoquinoline was found to have significant bronchodilating as well as hypotensive actions, as briefly communicated in the previous report (1). This compound ha d been synthesized by Pyman in 1909 (2) and its hypotensive action was reported by Laidlaw in the following year (3). While our work was in progress, Holtz and his co-workers (4) demonstrated the formaton of this compound as a condensation product of dopamine and its enzymatically deaminated product, 3, 4-dihydroxyphenyl-acetaldehyde. They also reported its hypotensive and bronchodilating activities, which were interpreted as a β-sympathomimetic action of this compound. In reference to these studies 1-aralkyl derivatives of tetrahydroisoquinoline (THI) were synthesized and tested their bronchodilating activities. Among the compounds tested, 1-(3, 4, 5-trimthoxybenzyl)-6, 7-dihydroxy-1, 2, 3, 4-tetrahydroisoquinoline (IX) was observed to be the most active bronchodilator hitherto described in the literature. The relationship between the chemical structure and the bronchodilating activity was investigated in this paper.

Isoquinoline誘導体の合成 (第2報)

Isoquinoline誘導体の合成 (第2報)

Synthesis of isoquinoline derivatives. I. Synthesis of 1,1'-biisoquinoline derivatives

Synthesis of isoquinoline derivatives. I. Synthesis of 1,1'-biisoquinoline derivatives

697. Pyrylium salts obtained by diacylation of olefins. Part III. Diacylation of cyclic olefins and a novel synthesis of isoquinoline derivatives

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273. Experiments on the synthesis of isoquinoline derivatives. Part III. A synthesis of corydaldine

273. Experiments on the synthesis of isoquinoline derivatives. Part III. A synthesis of corydaldine

372. Experiments on the synthesis of isoquinoline derivatives. Part II

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CCLXXIX.—Experiments on the synthesis of isoquinoline derivatives. Part I

CCLXXIX.—Experiments on the synthesis of isoquinoline derivatives. Part I