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Water and organic synthesis: A focus on the in-water and on-water border. Reversal of the in-water breslow hydrophobic enhancement of the normal endo -effect on crossing to on-water conditions for huisgen cycloadditions with increasingly insoluble organic liquid and solid 2pi-dipolarophiles

Measurements of the endo/exo product ratios for Huisgen cycloadditions with a series of vinyl ketones, alkyl acrylates, and substituted styrenes as dipolarophiles with phthalazinium and pyridazinium dicyanomethanide 1,3-dipoles in acetonitrile and water show that as the reactions change from in-water (large hydrophobic enhancement of endo-products) to on-water, the hydrophobic enhancement of the endo-products is reduced and partially reversed (relative to acetonitrile). An expected increase of the endo-effect with increasing hydrophobic character of the dipolarophile is overcome by decreasing water solubility causing changeover to on-water conditions. On-water reactions do not show increased cycloaddition endo-effects (relative to organic solvents) as do in-water reactions.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N91 – PubChem

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Synthesis, spectral characterization and antimicrobial studies of new hybrid heterocyclic compounds bearing 1H-benzimidazol-2-yl thiomethyl motif

To understand the biological importance of heterocyclic cores, novel 1H-benzimidazol-2-yl thiomethyl incorporated hybrid compounds, 2-(benzimidazol-2-ylthiomethyl)-5-Aryl-1,3,4-oxadizoles and 1-(2-(1H-benzo[d]imidazol-2-ylthio)acetyl)pyridazine/phthalazinediones were designed using molecular hybridization technique, synthesized and characterized. The compounds were screened for in vitro antimicrobial activity using the serial dilution technique and were found to exhibit weak antitubercular activity, excellent to moderate antibacterial and better antifungal activities against some tested organisms in comparison to the standard drugs. Thus, some of the title compounds demonstrated antimicrobial activity.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N123 – PubChem

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External Heavy Atom Effect on Intersystem Crossing of Radical Pair in Solvent Cage. Photoreactions of Phthalazine

External heavy atom effects have been studied for the photoreaction of phthalazine in 2-propanol.Addition of bromine containing compounds alters the product distribution in the dual photoreactions occured simultaneously.The results can be interpreted in terms of enhancement of the intersystem crossing from the triplet radical pair to the singlet radical pair, including the spin inversion within the solvent cage.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N200 – PubChem

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NOUVEAUX DERIVES PYRIDAZINIQUES ET PHTALAZINIQUES DOUES D’ACTIVITE PHYSIOLOGIQUE

This paper reports eleven new pyridazines and phthalazines derivatives. Products 5-11 have been obtained starting from 3-chloro-6-hydrazino-pyridazine (4), by means of various reactions. Products 14-16 belong to the class of phthalazinium-ylids. The biological tests have shown the antimicrobial activity of products 14, 15 and 16. For the other products biological tests are still under way.

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Reference£º
Phthalazine – Wikipedia,
Phthalazine | C8H6N99 – PubChem

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N-Chlorination-induced, oxidative ring contraction of 1,4-dimethoxyphthalazines

A rarely explored oxidative ring contraction of electron-rich 1,2-diazine is described. Upon treatment with an electrophilic chlorinating reagent (TCICA), 1,4-dimethoxyphthalazines undergo an N-chlorination-induced ring contraction that is accompanied by the loss of one nitrogen atom. The scope of this unusual reactivity was examined with a range of 1,4-dimethoxyphthalazine derivatives. In addition, a mechanism proceeding via a bicyclic species was proposed on the basis of an isolated reaction intermediate and DFT calculations.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N198 – PubChem

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One pot synthesis of pyrazolo phthalazine dione derivatives under microwave irradiation

In this method, we have reported the catalytic ability of boric acid as a green, eco-friendly catalyst for one-pot four component condensation reaction of phthalic anhydride, Monohydrate hydrazine, Malononitrile and substituted aromatic aldehyde was reported. The major synthetic protocol is the use of inexpensive, nontoxic, avoiding the use of harmful organic solvent, short reaction time, mild condition reaction, simple procedure, excellent yield and environmentally benign.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N239 – PubChem

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SULFUR CONTAINING DIHYDROPHTHALAZINE ANTAGONISTS OF EXCITATORY AMINO ACID RECEPTORS

Substituted dihydrophthalazine sulfur containing compositions are provided which are active as non-NMDA ionotropic excitatory amino acid (EAA) receptor antagonists. The compositions are useful for treating disorders associated with excessive activation of the non-NMDA subtype of the ionotropic EAA receptor. The compounds further are useful as testing agents to identify and characterize other compounds for the treatment of these disorders. The compounds are useful therapeutically as sedatives or for the treatment of neurosychopharmacological disorders such as stroke, ischemia and epilepsy. The compositions may be provided in combination with a suitable carrier for oral or parenteral administration. The compounds may be administered orally or parenterally for the treatment of a variety of disorders associated with non-NMDA EEA receptor function.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N13 – PubChem

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Reactivity of Highly Lewis-Acidic Diborane(4) toward C?N and N=N Bonds: Uncatalyzed Addition and N=N Bond-Cleavage Reactions

The diboration of the C?N bond in organic nitriles, and the N=N bond in azobenzene and pyridazine, by the highly Lewis-acidic tetra(o-tolyl)diborane(4) are reported. In the reactions with nitriles, azobenzene, and pyridazine, the addition of diborane(4) to the C?N and N=N bonds was observed. Conversely, the N=N bond in phthalazine was cleaved by an addition/rearomatization sequence.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N225 – PubChem

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Classification of scaffold-hopping approaches

The general goal of drug discovery is to identify novel compounds that are active against a preselected biological target with acceptable pharmacological properties defined by marketed drugs. Scaffold hopping has been widely applied by medicinal chemists to discover equipotent compounds with novel backbones that have improved properties. In this article we classify scaffold hopping into four major categories, namely heterocycle replacements, ring opening or closure, peptidomimetics and topology-based hopping. We review the structural diversity of original and final scaffolds with respect to each category. We discuss the advantages and limitations of small, medium and large-step scaffold hopping. Finally, we summarize software that is frequently used to facilitate different kinds of scaffold-hopping methods.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N427 – PubChem

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Preparation of Perfluoroalkyl Azaarenes with a Perfluoroalkyllithium-Boron Trifluoride System

In the presence of Borontrifluoride, perfluoroalkyllithiums generated in situ from the reaction of n-perfluoroalkyl iodides with methyllithium-lithium bromide smoothly added to a carbon-nitrogen double bond of bicyclic azaarenes and diazines to give the corresponding perfluoroalkylated dihydro heterocycles, which often underwent spontaneous aromatization in air.Perfluoroalkylation occured preferentially at the carbon next to nitrogen in azaarenes even when the carbon atom was occupied by an alkyl substituent.Only one exception observed was the reaction of acridine where a perfluoroalkyl group was introduced at 9 position.

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Reference£º
Phthalazine – Wikipedia,
Phthalazine | C8H6N455 – PubChem