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Interplay of thermochemistry and Structural Chemistry, the journal (volume 29, 2018, issues 3?4) and the discipline

The contents of issues 3 and 4 of Structural Chemistry from the calendar year 2018 are summarized in the present review. A brief thermochemical commentary and recommendations for future research have been added to the summary of each paper.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N345 – PubChem

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Synthesis of 5-Azaindolizine Derivatives by the Palladium-Catalyzed Intermolecular Formal [3+2] Cycloaddition of Alkylidenecyclopropanes with 1,2-Diazines

The palladium-catalyzed formal [3+2] cycloaddition reaction of alkylidenecyclopropanes with 1,2-diazines proceeded smoothly to give the corresponding 5-azaindolizine derivatives in good to allowable yields. For example, in the presence of 5 mol % of Pd(PPh3)4, the reaction of 1-propyl-hexylidenecyclopropane with phthalazine or with pyridazine proceeded at 120 C without solvent, and the corresponding 2-(1-butylpentyl)pyrrolo[2,1-a]phthalazine or 6-(1-butylpentyl)pyrrolo[1,2-b]pyridazine was obtained in 61% or 49% yield, respectively.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N413 – PubChem

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Contributions to syntheses of pyrrolo[2,1-a]phthalazines

Structural elucidation of the dihydro derivatives obtained as by-products in the classic salt method synthesis of pyrrolo[2,1-a]phthalazines and acetylenic dipolarophiles was achieved by X-ray diffraction analysis of a representative compound. In addition, new pyrrolo[2,1-a]phthalazines were obtained by a one-pot three-component reaction that avoids the formation of the dihydro derivative intermediates. Springer-Verlag 2011.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N95 – PubChem

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A new photochromic system based on a pyridazinopyrrolo[1,2-b]pyridazine with ultrafast thermal decoloration

The nucleophilic addition of the substituted pyridazines 2a-e to diacetylspirocyclopropene (1) in dry ether solution afforded the dihydroindolizines 3a-e, which undergo ring opening to the betaine 3?a-e after irradation with UV light. Condensation of the diacetyl groups of the dihydroindolizines (DHIs) 3a-e with hydrazine hydrate in a diethyl ether/ethanol mixture gave the new pyridazinopyrrolo[1,2-b]pyridazines 4a-e. Compounds 4a-e showed no photochromism at room temperature or after cooling with liquid nitrogen. However laser flash spectroscopy was successfully used for the determination of both the half-life and absorption maxima of the betaines 4?a-e.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N155 – PubChem

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Fragmentation Reactions of Molecular Dications of Aromatic Heterocyclic Fused-ring Compounds Containing More Than One Nitrogen Atom

Fragmentation reactions of both metastable and collisionally activated dications, formed by electron impact ionization of heterocyclic fused-ring aromatic compounds containing more than one nitrogen atom, were investigated.This work is an extension of similar work on analogous compounds containing just one nitrogen atom and on the related polycyclic aromatic hydrocarbons.The results obtained are interpreted in terms of mechanistic proposals concerning the competition between charge-separation and neutral-expulsion reactions, based on variations in diradical characterwith increasing molecular size and nitrogen content of these molecular dications.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N339 – PubChem

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Self-assembly of ID- And 3D-networks through non-coordination intermodular forces: Synthesis and crystal structures of copper(I) complexes based on pyridazine-type ligands

Reaction of [Cu2(H3CCN)2(mu-pydz) 3][PF6]2 (1) with an excess of pyridazine or phthalazine yielded the novel dinuclear complexes [Cu2(mu-pydz) 3(pydz)2][PF6]2 (2) and [Cu 2(mupydz)(mu-phtz)2(phtz)2][PF 6]2 (5), respectively. Depolymerisation of the coordination polymer ?1{[Cu(mu-pydz) 2][PF6]} (3) in dichloromethane by addition of an excess of benzo[c]cinnoline afforded the dinuclear copper(I) salt [Cu 2(mu-pydz)2(pydz)2(benzo[c]cinnoline) 2][PF6]2 (4). Furthermore, a new route for the preparation of bis(benzonitrile)tris(mu-phthalazine)dicopper(I) bis(trifluoromethanesulfonate), [Cu2(C6H 5CN)2(i-phtz)3][CF3SO 3]2 (7), was established from {[Cu(CF3SO 3)]2 ¡¤C6H5Me}, phthalazine and benzonitrile via the very air-sensitive intermediate [Cu2(CF 3SO3)2(mu-phtz)3] (6). Copper(I) compounds 2, 4, and 7 were completely characterised and the molecular structures confirmed in the solid state by single-crystal X-ray structure determination. The analysis of the packing of the molecules in crystals of 4 and 7 revealed a self-assembly of oneand three-dimensional frameworks, respectively, resulting from intermolecular pi-pi stacking interactions between pyridazine-type ligands.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N343 – PubChem

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Synthesis and Anticonvulsant Activity Evaluation of Phthalazine and Heterocyclic Derivatives

Four series of derivatives, 6-substituted-1,2,4-triazolo[3,4-a] phthalazine derivatives and 6-substituted tetrazolo[5,1-a]phthalazine derivatives have been synthesized. The structures of compounds are confirmed by 1H NMR, 13C NMR, IR and HRMS. The anticonvulsant effects of the compounds are evaluated with maximal electroshock test by intraperitoneally injected in mice. The experimental results show that N-(4-bromophenyl)tetrazolo[5,1-a]phthalazin-6-amine (7a) was the most potent compound, with a median effective dose of 5.89 mg¡¤kg-1. Its anticonvulsant effect is better than the reference drug, carbamazepine.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N506 – PubChem

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Synthesis, biological, anti-inflammatory activities and quantum chemical calculation of some [4-(2, 4, 6-trimethylphenyl)-1(2H)-oxo-phthalazin-2yl] acetic acid hydrazide derivatives

The phthalazine carbohydrazide 2 was prepared and incorporated into the corresponding 1,2,4-triazole and carbamate derivatives. Phthalazine carboxylic acid hydrazide 2 was treated with isatine and cyclo-hexanone to give the corresponding hydrazone derivatives 16, 19 in good yields. Furthermore, alpha-amino acid derivative conjugated with 1-oxophthalazine moiety 35 was synthesized by the reaction of the corresponding aizde 28, via the azide-coupling method, with glycine methyl ester. The peptide ester 35 was converted into their corresponding amide 36 by treating with methanolic ammonia. Moreover, 35 was boiled with hydrazine hydrate to afford the corresponding hydrazide 37. Finally, the dipeptide 38 was prepared by coupling of 35 with L-alanine methyl ester. Some of these compounds were screened in vitro for their antimicrobial activity. The energy gap between the highest occupied molecular orbital and lowest unoccupied molecular orbital has been calculated using the theoretical computations to reflect the chemical reactivity and kinetic stability of compounds.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N140 – PubChem

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Combining Bidentate Lewis Acid Catalysis and Photochemistry: Formal Insertion of o-Xylene into an Enamine Double Bond

A bidentate Lewis acid catalyzed domino inverse-electron-demand Diels-Alder reaction combined with a photoinduced ring opening formally inserts o-xylene moieties into enamine double bonds. After reduction, phenethylamines were obtained in good yields. The scope of the reaction was determined by variation of all three starting compounds: phthalazines, aldehydes, and amines.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N24 – PubChem

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Visible-Light-Induced Copper-Catalyzed Decarboxylative Coupling of Redox-Active Esters with N-Heteroarenes

Herein we report a protocol for visible-light-induced copper-catalyzed decarboxylative coupling reactions between N-heteroarenes and redox-active esters. Various N-hydroxyphthalimide esters reacted with isoquinoline, quinoline, pyridine, pyrimidine, quinazoline, phthalazine, phenanthridine, and pyridazine to give the corresponding products in modest to excellent yields. The reactions proceed under mild conditions and have a broad scope and high functional group tolerance. Mechanistic studies revealed that the catalytic behavior of CuI photocatalyst generated in situ was consistent with that of preformed [Cu(dmp)(xantphos)]BF4.

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Phthalazine – Wikipedia,
Phthalazine | C8H6N271 – PubChem