Synthesis of the parent compound and N-substituted derivatives of 1H-benz[de]isoquinoline and benz[de]isoquinolinium-1-ide

Sha, C.K.; Wang, Deh-Chi

doi:10.1016/s0040-4020(01)90477-6

Cited by 13 publications

(8 citation statements)

References 9 publications

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“…The dehydrochlorination of 7 with a mild base (e.g., diisopropylethylamine, triethylamine) affords the unstable 2-azaphenalene 8b , characterized by in situ 1 H NMR and EI mass spectroscopy. Compound 8b easily isomerizes to the reactive azomethine ylide 9 in the presence of excess base, the latter characterized by trapping with N -phenylmaleimide as found in a different study . Compound 8b is very easily oxidized by air to the yellow-green radical 2 , which decomposes much more slowly in the presence of excess air to give several polar products and baseline material.…”

Section: Resultsmentioning

confidence: 74%

Synthesis, Characterization, and Coordination Chemistry of the 2-Azaphenalenyl Radical

et al. 2003

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The 2-azaphenalenyl radical 2 has been synthesized and characterized by ESR spectroscopy. Variable-temperature ESR measurements were carried out on both the phenalenyl (1) and the 2-azaphenalenyl (2) radicals. The phenalenyl radical 1 has the known propensity to dimerize at temperatures below 20 degrees C, but unexpectedly less so than originally reported. The first experimental measurement of bond dissociation enthalpy for the dimerization of the phenalenyl radical 1 was obtained in CCl(4) (11.34 +/- 0.11 kcal/mol) and toluene (9.8 +/- 0.7 kcal/mol). The 2-azaphenalenyl radical 2 does not show a propensity to dimerize over the measurable temperature range (220-330 K), but does so in the presence of Cu(hfac)(2) (hfac = hexafluoroacetylacetonate). The latter complex was characterized by X-ray crystallography.

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Section: Resultsmentioning

confidence: 74%

Synthesis, Characterization, and Coordination Chemistry of the 2-Azaphenalenyl Radical

et al. 2003

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“…The bromomethyl group was oxidised with 2-nitropropane. 122 1,4-Naphthodialdehyde was prepared from 1,4-bis(bromomethyl)naphthalene by the Sommelet reaction. 123 Isomeric 1,3-, 1,5-, 1,6-, 1,7-, 2,6-and 2,7-dialdehydes as well as 1,3,5-, 1,3,6-, 1,3,7-and 1,4,6-trialdehydes of the naphthalene series were synthesised according to the KroÈ hnke method.…”

Section: Syntheses Based On Halomethylnaphthalenesmentioning

confidence: 99%

“…For other naphthaldehydes, analogous reactions were documented. 58,185 Naphthaldehydes gave condensation products with compounds containing the active methylene group, viz., diethyl malonate ester, 122,186 malononitrile, 186 ± 188 esters of cyanoacetic 186 and other carboxylic acids, 89 benzyl cyanides, 52,187 g-picoline, 98 barbituric acid, 189 trinitrotoluene, 60 etc.…”

Section: Reactionsmentioning

confidence: 99%

“…These reactions afford alkenes, which are generally used for subsequent cyclisations, including the synthesis of natural compounds, 196 biologically active substances 133 and synthetic precursors of fullerene. 197 The syntheses of 6,7-bis(dimethylamino)phenalenone (183), 186 naphtho[1,8-b,c]pyran (184) 78 (a modification of this synthesis was described in the study 198 ), 1-methylbenzo[d,e]quinoline (185) 160 and benzo[d,e]isoquinoline (186) 122 provide only a few examples of such transformations. An analogous approach was used for the synthesis of linear and angular naphthofurans and benzocoumarins.…”

Section: Reactionsmentioning

confidence: 99%

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Naphthaldehydes

Пожарский¹

2003

Russ. Chem. Rev.

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Data on methods for the preparation of naphthalde-Data on methods for the preparation of naphthaldehydes, their physicochemical properties, structural characteristics hydes, their physicochemical properties, structural characteristics and reactivities are generalised. Particular attention is given to and reactivities are generalised. Particular attention is given to procedures for formylation of naphthalenes and procedures for formylation of naphthalenes and peri peri-interactions -interactions involving the aldehyde group in the involving the aldehyde group in the a a-position. The bibliography -position. The bibliography includes 201 references includes 201 references. .

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“…1a. The isomers includes 1azaphenalene 3 6 and 9b-azaphenalene (cycl [3.3.3]azine) 4 7 , which have been synthesized, and N-substituted-2-azaphenalenyl (benzo[de]isoquinolinium-1-ide) 5 8,9 and 9a-azaphenalenyl 6, which serve as highly reactive azomethine ylides intermediates ( Fig. 1b and Supplementary Fig.…”

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confidence: 99%

Isolation and characterisation of a stable 2-azaphenalenyl azomethine ylide

et al. 2019

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Although azomethine ylides have been fully exploited as versatile reactive intermediates in dipolar cycloaddition reactions to construct a variety of heterocyclic compounds involving a nitrogen atom, little is known about their structural and electronic properties. Here a method is developed for the preparation, isolation and characterization of a stable 2-azaphenalenyl based azomethine ylide. N-Phenyl-5,8-di-t-butyl-2-azaphenalenyl cannot be isolated because it undergoes rapid dimerization by CC bond formation at the 1 and 3 positions. In contrast, sterically bulkier N-2,6-di(isopropyl)phenyl-5,8-di-t-butyl-2-azaphenalenyl can be generated and isolated as deep green crystals under deoxygenated conditions. X-ray crystal analysis of this stable azomethine ylide reveals that its azaphenalenyl skeleton has very small bond alternation and structural deformation. The results of spectroscopic and electrochemical theoretical studies indicate that N-2,6-di(isopropyl)phenyl-5,8-di-t-butyl-2-azaphenalenyl has electronic features that are similar to those of phenalenyl anion and it possesses an extremely high HOMO energy.

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Synthesis of the parent compound and N-substituted derivatives of 1H-benz[de]isoquinoline and benz[de]isoquinolinium-1-ide

Cited by 13 publications

References 9 publications

Synthesis, Characterization, and Coordination Chemistry of the 2-Azaphenalenyl Radical

Synthesis, Characterization, and Coordination Chemistry of the 2-Azaphenalenyl Radical

Naphthaldehydes

Isolation and characterisation of a stable 2-azaphenalenyl azomethine ylide

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