Pyridazinium ylides II. New carbanion disubstituted ylides

Mangalagiu, Ionel I.; Petrovanu, M.

doi:10.1016/s0040-4020(97)00111-7

Cited by 9 publications

(3 citation statements)

References 7 publications

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“…According to the literature indications [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20] the chemistry of cycloiminium ylides is widely discussed. In previous research work we have studied the synthesis, structure, and reactivity of some 1,2-diazinium ylides [12][13][14] (derived from pyridazine and phthalazine) as well as of 1,3-diazinium ylides [15][16][17] (derived from 4-methylpyrimidine).…”

Section: Introductionmentioning

confidence: 99%

“…In previous research work we have studied the synthesis, structure, and reactivity of some 1,2-diazinium ylides [12][13][14] (derived from pyridazine and phthalazine) as well as of 1,3-diazinium ylides [15][16][17] (derived from 4-methylpyrimidine). Our main target was to study the chemistry of diazinium ylides and to find correlations between structure-stability-reactivityproperties [biological, 18 acido-basic, 19 electrical (semiconducting properties 20 ) etc.].…”

Section: Introductionmentioning

confidence: 99%

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4-(4-Chloro-phenyl)-pyrimidinium ylides. 1. Structure, stability, reactivity

Moldoveanu¹,

Mangalagiu²,

Caprosu³

et al. 2004

Arkivoc

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In this paper we present a theoretical and experimental study concerning the structure, stability, and reactivity of 4-(4-chlorophenyl)pyrimidinium ylides. 4-(4-Chlorophenyl)-pyrimidinium ylides are relatively stable compounds, their stability varying with the nature of the ylide carbanion substituent. The stronger the electron-withdrawing effect of these substituents, the more the anionic charge is delocalized, and therefore the higher their stability. The experimental and quantum chemical calculations confirm this hypothesis and are in accordance with each other. The electronic absorption spectra of 4-(4-chlorophenyl)-pyrimidinium 4-X-benzoyl methylides can be assigned to an intramolecular charge transfer band. The quantum chemical calculations show the possibility to use pyrimidinium ylides as nucleophilic reagents as well as 1,3-dipoles in reaction with appropriate reagents. The influence of microwave irradiation for the synthesis of azinium salts was also studied. The reaction of 4-(4-chlorophenyl)pyrimidine with an organic haloalkane shows a remarkable rate acceleration under microwave irradiation and allows a general and facile synthesis of azinium salts. A comparative study of microwave and classical conditions (use of solvents) has been done.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

4-(4-Chloro-phenyl)-pyrimidinium ylides. 1. Structure, stability, reactivity

Moldoveanu¹,

Mangalagiu²,

Caprosu³

et al. 2004

Arkivoc

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“…Because of the industry demand, there is a constantly increasing interest for synthesis of new chemical entity with azaheterocyclic skeleton [1]. There are a large variety of synthesis pathway, these including conventional [2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17] chemistr y (organometalic, cycloimmonium ylides chemistry, etc) and nonconventional chemistry using microwave [18][19][20][21][22][23][24][25][26][27][28][29] and ultrasound tehnology [30][31][32][33][34][35][36]. As far for potential practical applications of azaheterocyclic derivatives, these spam pharmaceutical and medicinal chemistry (anticancer, antimicrobials, anti-inflammatory, antihypertensive, diuretics, antithrombics, anticoagulants, antidepressant, anxiolytics, anticonvulsant, analgesic) [37][38][39][40][41][42][43][44][45]…”

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Synthesis and Structure of a New Class of Fused Heterocycle with 8,9-Dihydro-pyridazino[1,2,4]triazine Skeleton

Humelnicu¹,

Vasilache²

2017

Rev. Chim.

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The synthesis and X-ray crystal structure of a new class of fused heterocycle with 8,9-dihydro-pyridazino[1,2,4]triazine type 2 is reported. The synthesis is facile and efficient and, the structure of compounds was proven by elemental and spectral analysis, the X-ray spectra including (for 2b). The compound crystallizes in the space group P21/N (monoclinic) with a = 9.0077(2) �, b = 10.20019(18) �, c = 14.0099(3) �, a= 90�, b = 89.768(2)�, g= 90�, V= 1287.22(5) and Z = 4. Accurate molecular parameters for the heterocyclic system were obtained from intensity data collected at 200(14) K. The molecule 8,9-dihydro-pyridazino[1,2,4]triazine type 2 is a noncoplanar bicyclic fused system, with an envelope shape onto the triazine moiety, the C12 carbon being out of plane. The methyl group from the C12 carbon it is almost perpendicular on the triazine plane. We also notice a rather powerful hydrogen bond between hydrogen atom from N1 and the oxygen from the C11=O1 carbonyl group.

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References

2000

Chemistry of Heterocyclic Compounds: A Series of Monographs

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Pyridazinium ylides II. New carbanion disubstituted ylides

Cited by 9 publications

References 7 publications

4-(4-Chloro-phenyl)-pyrimidinium ylides. 1. Structure, stability, reactivity

4-(4-Chloro-phenyl)-pyrimidinium ylides. 1. Structure, stability, reactivity

Synthesis and Structure of a New Class of Fused Heterocycle with 8,9-Dihydro-pyridazino[1,2,4]triazine Skeleton

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