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Carbon-13 and Proton NMR Spectra of 1(2H)-Isoquinolinone, 1(2H)-Phthalazinone, 4(3H)-Quinazolinone and their Substituted Derivatives

The 13C NMR chemical shifts, one-bond and some long-range 13C-1H coupling constants and the 1H NMR chemical shifts for isoquinolinone, phthalazinone, quinazolinone and their derivatives containing CH3, COOH, COOCH3 and CH2COOH substituents in the hetero-ring are reported.The NMR data are in agreement with the lactam structure for all compounds studied; no evidence for the detectable presence of other tautomers was obtained.

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Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

 

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A direct metal-free C2-H functionalization of quinoline N-oxides: A highly selective amination and alkylation strategy towards 2-substituted quinolines

An efficient one-pot methodology for C2-selective amination and alkylation of quinoline N-oxides towards 2-substituted quinolines was developed, via the reaction of various quinoline N-oxides with ammonia, a large variety of primary and secondary amines, as well as active methylene compounds in the presence of diethyl H-phosphonate and K2CO3 under metal free conditions at room temperature.

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The chemistry of an isolable azomethine ylide

The 4-isoxazoline 3 undergoes ring contraction to the acylaziridine 5 which is converted to the azoraethine ylide 4. The small influence of solvent polarity on the rate constant of the conversion 3 ? 4 suggests a mechanism via a trimethylene type species for the rate-determining step. Whereas 4 is the first azomethine ylide which can be isolated without being stabilized by aromatic resonance, the ylides 20-22 dimerize to piperazine derivatives. 1,3-Dipolar cycloadditions of the azomethine ylides 4 and 20-22 are described.

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Tertiary amine oxidation using HOF-CH3CN: A novel synthesis of N-oxides

HOF·CH3CN, probably the best oxygen transfer agent organic chemistry has to offer, is easily made by bubbling diluted fluorine (10-15%) through aqueous acetonitrile solution. Used as formed without any isolation or purification, it reacts with various tertiary amines such as pyridine derivatives, polyaromatic nitrogen containing compounds and aliphatic and alicyclic ones to form the corresponding N-oxides. When two nitrogen atoms are present it is possible to make both the N-monoxides and the N,N-dioxides. The reaction times are short (a few minutes), conditions are very mild (0-25 C) and the yields range from good to excellent (70-95%).

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Unraveling the metabolic response of Brassica oleracea exposed to Xanthomonas campestris pv. campestris

BACKGROUND: Brassica crops together with cereals represent the basis of world supplies. Due to their importance, the production losses caused by Xanthomonas campestris pv. campestris (Xcc) infection represent a high economic impact. Understanding molecular and biochemical mechanisms of plants is essential to develop resistant crops with durable protection against diseases. In this regard, metabolomics has emerged as a valuable technology to provide an overview of the biological status of a plant exposed to a disease. This study investigated the dynamic changes in the metabolic profile of Brassica oleracea plants during an Xcc infection from leaves collected at five different days post infection using a mass spectrometry approach. RESULTS: Results showed that Xcc infection causes dynamic changes in the metabolome of B. oleracea. Moreover, induction/repression pattern of the metabolites implicated in the response follows a complex dynamics during infection progression, indicating a complex temporal response. Specific metabolic pathways such as alkaloids, coumarins or sphingolipids are postulated as promising key role candidates in the infection response. CONCLUSION: This work tries to decipher the changes produced on Brassica crops metabolome under Xcc infection and represents a step forward in the understanding of B. oleracea?Xcc interaction.

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Conjugated enynones: Preparation, properties and applications in organic synthesis

Published data on the preparation methods, properties and chemical transformations of linear- and cross-conjugated enynones are integrated. The molecular and crystal structures, spectral characteristics and non-linear optical properties of these compounds are considered. Data on the reduction of enynones to alcohols and on electrophilic, nucleophilic and pericyclic reactions involving them are described systematically. Primary attention is paid to the regioselectivity and mechanisms of transformations of conjugated enynones. Examples of their application in the targeted organic synthesis of carbo- and heterocyclic compounds are given.

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A general and efficient 2-amination of pyridines and quinolines

(Chemical Equation Presented) Pyridine N-oxides were converted to 2-aminopyridines in a one-pot fashion using Ts2O-t-BuNH2 followed by in situ deprotection with TFA. The amination proceeded in high yields, excellent 2-/4-selectivity, and with good functional group compatibility. 2-Amino (iso)quinolines were also obtained in the same manner. Combined with the simple oxidation of pyridines to pyridine N-oxides, this method provides a general and efficient way for amination of 2-unsubstituted pyridines.

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Palladium(II)-catalyzed C-C and C-O bond formation for the synthesis of C1-benzoyl isoquinolines from isoquinoline: N -oxides and nitroalkenes

C1-Benzoyl isoquinolines can be generated via a palladium(ii)-catalyzed C-C and C-O coupling of isoquinoline N-oxides with aromatic nitroalkenes. The reaction proceeds through remote C-H bond activation and subsequent intramolecular oxygen atom transfer (OAT). In this reaction, the N-O bond was designed as a directing group in the C-H bond activation as well as the source of an oxygen atom.

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The NiCl2-Li-Arene (cat.) Combination as Reducing System, Part 9: Catalytic Hydrogenation of Organic Compounds using the NiCl 2-Li-(Naphthalene or Polymer-Supported Naphthalene) (cat.) Combination

The reaction of lithium powder, a catalytic amount of naphthalene or polymer-supported naphthalene, and anhydrous nickel(II) chloride, in THF at room temperature, generates a finely divided and very reactive nickel(0) which has been efficiently applied to the catalytic hydrogenation of different organic compounds such as alkenes, alkynes, carbonyl compounds, imines, organic halides, aromatic compounds, hydrazines, azoxy compounds, and N-oxides.

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A novel method for the synthesis of 3-(2-quinolyl) chromones through a tandem [3+2] cycloaddition/ring-opening/O-arylation from ynones and quinoline N-oxides has been developed. This protocol proceeds under transition metal- and additive-free conditions and can be amplified to the gram level in 91% yield. 3-(1-Isoquinolyl) and 3-(2-pyridyl) chromones are also successfully synthesized using isoquinoline and pyridine N-oxides under basic conditions. Various heteroarene-contaning chromones were afforded in 30-98% yields, which are difficult to be obtained and are compounds of interest in pharmaceutical chemistry and chemical biology.

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