Reaction Of Diimine Research Articles

Polycyclic derivatives of hexacoordinated phosphorus atom with transannular N→P bond

Reaction of diimine I containing phenol groups with ethylenechlorophosphite II was established to undergo a stereoselective cascade cyclization giving rise to tetracyclic derivative III of the hexacoordinated phosphorus atom with intramolecular transannular N→P bond. The structure of compound III was proved by the IR, Н and Р NMR spectroscopy, mass spectrometry, X-ray diffraction method, and the composition was established by the elemental analysis data. The IR spectrum of the product III contains absorption bands at 1629 (С=N) and 2500–2680 cm (broadened complex band, NH2). The chemical shift of the phosphorus atom δP –115.84 ppm is characteristic of the phosphorus hexacoordinated derivatives. Due to salt structure, the Н NMR spectrum of compound III contains poorly resolved signals permitting only group analysis of the protons on the basis of chemical shifts without considering its fine structure. By the elemental analysis data compound III has the overrated percentage of chlorine. This suggests that the compound contains a solvent, methylene chloride. This conclusion was confirmed by the X-ray diffraction data. The product III actually crystallized as a complex with methylene chloride molecule as one diastereoisomer. Configurations of asymmetrical centers on the carbon and phosphorus atoms are opposite. The transannular N→P bond length is 2.006(6) A. The intermolecular bonding of similar type was earlier observed in the series of hexacoordinated phosphorus derivatives [1–5]. DOI: 10.1134/S1070363210020325

ChemInform Abstract: Studies on the Reaction of Diimines with Thiourea: Synthesis and Solvent‐Induced cis/trans‐Isomerization of 1,3,5‐Triazinane‐2‐thiones.

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Studies on the Reaction of Diimines with Thiourea: Synthesis and Solvent-Induced cis/trans-Isomerization of 1,3,5-Triazinane-2-thiones

The reaction of N,N'-bis(arylmethylidene)arylmethane diimines with thiourea under reflux in methanol was studied. The reaction gave a diastereomeric mixture of 4,6-disubstituted 1,3,5-triazinane-2-thiones in good yields. Two diastereoisomers of 4,6-diphenyl-1,3,5-triazinane-2-thione were detected in a solution of CDCl 3 by NMR analysis. According to the NMR studies, the cis-diastereoisomer undergoes a solvent-induced cis/trans-isomerization process, producing the trans-diastereoisomer in DMSO. The stereochemistry of the trans-diastereoisomer was determined by X-ray crystallographic analysis.

ChemInform Abstract: Reaction of Diimines and Azines with Diphenylcyclopropenone.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Reaction of diimines and azines with diphenylcyclopropenone

1-Cyclohexyl-2-cyclohexylaminomethylene-4,5-diphenyl-1,2-dihydropyrrol-3-one 4a and 1-aryl-2-arylaminomethylene-4,5-diphenyl-1,2-dihydropyrrol-3-ones 4b,c as the E-form are synthesized by the reaction between N,N′-dicyclohexylethane-1,2-diylidenediamine 2a and N,N′-diarylethane-1,2-diylidenediamines 2b,c with diphenylcyclopropenone 1 through a formal [2 + 3] cycloaddition reaction. The structure assignment of 4a is confirmed on the basis of an X-ray crystal-structure determination. Similarly, diaryl azines 8a–c react with 1 through a formal [2 + 3] cycloaddition reaction to give the non-isolable product Δ4-pyrrolin-3-ones 10a–c which undergo oxidative rearrangement to afford ultimately the indenone derivatives 9a–c.

ChemInform Abstract: Reaction of Diimines and Benzyne.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Reaction of diimines and benzyne

The reaction between benzyne and the Schiff bases 1a,b and 15a,b leads to the 1,4-bis(2‵-substituted acridin-10-yl)benzene 4a,b, the N-phenylarylamines 10a,b and the 10-(4‵-formylphenyl)-substituted acridines 11a,b (from 1a,b) and the 2-substituted acridine-10-carboxyaldehyde 18a,b (from 15a,b). Cyclohexyl (4-cyclohexyliminomethylbenzylidine)amine 1c reacts with benzyne by an ene-reaction to give cyclohexenyl[(4-cyclohexyliminomethylphenyl)benzylidine]amine 14.

Interesting products derived from the reactions of 2,3-diamino-2,3-dimethylbutane

The diimine, N,N'-dibenzylidene-2,3-diamino-2,3-dimethylbutane (10), was successfully synthesized from 2,3-diamino-2,3-dimethylbutane (3) by reaction with excess benzaldehyde. The reaction of diimine (10) with permanganate/PTC at pH=4.1 did not give the corresponding dinitrone (11) but unexpectedly gave 3-benzoyl-4,4,5,5-tetramethyl-2-phenylimidazoline (13) in 45% yield. The imidazoline (13) was independently prepared by benzoylation of 4,4,5,5-tetramethyl-2-phenylimizoline (9) which had been synthesized from diamine (3) and methyl benzimidate. The cyclic α-dinitrone, 2,3-dihydro-2,2,3,3,5,6-hexamethylpyrazine 1,4-dioxide (4), synthesized from N,N'-dihydroxy-2,3-diamino-2,3-dimethylbutane (2) and 2,3-butanedione, underwent ozonolysis to yield the corresponding vicinal dinitro compound, 2,3-dimethyl-2,3-dinitrobutane (1), quantitatively

Reaction of Diimines with Carbonyl Compounds. Synthesis of Dihydropyrimidines

Reaction of Diimines with Carbonyl Compounds. Synthesis of Dihydropyrimidines

Reaction of Diimines with Acetylenedicarboxylic Acid Esters. Synthesis of 2-Oxo-1,2-dihydropyridines

Reaction of Diimines with Acetylenedicarboxylic Acid Esters. Synthesis of 2-Oxo-1,2-dihydropyridines

Pericyclic reactions of diimine

Pericyclic reactions of diimine

Pericyclic reactions of diimine

Pericyclic reactions of diimine