Iminophosphoranes: Useful Building Blocks for the Preparation of Nitrogen-Containing Heterocycles

Molina, P.; Vilaplana, M. J.

doi:10.1055/s-1994-25672

Cited by 325 publications

(143 citation statements)

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“…[5][6][7] In this paper the application of Suzuki -condensation ring closure tandem reaction is described for the synthesis of a novel thieno[3′,2′:4,5]pyrido [2,3-d]pyridazine ring system. Among starting material of our previous works also 5-azido-4-bromopyridazin-3(2H)-ones derivatives have been applied for synthesis route azide→iminophosphorane→Suzuki-aza-Wittig tandem reaction.…”

Section: Introductionmentioning

confidence: 99%

Tandem mass spectrometric study of annelation isomers of the novel thieno[3′,2′:4,5]pyrido[2,3-d]pyridazine ring system

Krajsovszky¹,

Tóth²,

Ludányi³

2014

Arkivoc

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In the present communication, we describe tandem combinations of Suzuki -condensation ring closure reactions to obtain a novel thieno[3′,2′:4,5]pyrido[2,3-d]pyridazine ring system. These compounds were studied by tandem mass spectrometry in detail and characteristic fragmentations were observed, which can be useful to confirm the presence of N-substituted pyridazine ring in synthesized compounds.

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Section: Introductionmentioning

confidence: 99%

Tandem mass spectrometric study of annelation isomers of the novel thieno[3′,2′:4,5]pyrido[2,3-d]pyridazine ring system

Krajsovszky¹,

Tóth²,

Ludányi³

2014

Arkivoc

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“…Phosphorus ylides are important reagents in synthetic organic chemistry [1][2][3][4][5][6], especially in the synthesis of naturally occurring products, compounds with biological and pharmacological activity [6]. The development of the modern chemistry of natural and physiologically active compounds would have been impossible without the phosphorus ylides [1][2][3][4][5][6].…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…The development of the modern chemistry of natural and physiologically active compounds would have been impossible without the phosphorus ylides [1][2][3][4][5][6]. They have found use in a wide variety of reactions of interest to synthetic chemists [1][2][3][4][5][6]. These compounds have attained great significance as widely used reagents for linking synthetic building blocks with the formation of carbon-carbon double bonds, and this has aroused much interest in the study of the synthesis, structure and properties of P-ylides and their derivatives [1][2][3][4][5][6].…”

Section: Introductionmentioning

confidence: 99%

“…They have found use in a wide variety of reactions of interest to synthetic chemists [1][2][3][4][5][6]. These compounds have attained great significance as widely used reagents for linking synthetic building blocks with the formation of carbon-carbon double bonds, and this has aroused much interest in the study of the synthesis, structure and properties of P-ylides and their derivatives [1][2][3][4][5][6]. Several methods have been developed for preparation of phosphorus ylides [1].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of stabilized phosphorus ylides from electron-poor alcohols and their applications in the preparation of 2,5-dihydrofuran derivatives

Salmanpour¹,

Ramazani²,

Ahmadi³

2012

Bull. Chem. Soc. Eth.

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ABSTRACT. Protonation of the highly reactive 1:1 intermediates, produced in the reaction between triphenylphosphine and dialkyl acetylenedicarboxylates, by alcohols (2-methanol thiophen, 3-methanol thiophen, 1,1,1,3,3,3-hexafluoro-2-propanol and [4-(trifluoromethyl)-phenyl]methanol) leads to vinyltriphenylphosphonium salts, which undergo Michael addition reaction with conjugate base to produce the corresponding stabilized phosphorus ylides. Wittig reaction of the stabilized phosphorus ylides with ninhydrin leads to the corresponding densely functionalized 2H-indeno[2,1-b]furans in fairly good yields.

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Surpassing Torquoelectronic Effects in Conrotatory Ring Closures: Origins of Stereocontrol in Intramolecular Ketenimine-Imine [2+2] Cycloadditions

et al. 1999

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Intramolecular ketenimine ± imine [22] cycloadditions leading to 1,2-dihydroazeto[2,1-b]quinazolines occur in a notably stereocontrolled manner along the newly formed C ± C single bond when prochiral ketenimine and imine fragments are combined. Computational studies support stepwise mechanisms for these reactions. In sharp contrast with other well-known [22] cycloadditions, the first step of the reaction determines its stereochemical outcome, thereby surpassing the low stereocontrol induced by torquoelectronic effects.

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Iminophosphoranes: Useful Building Blocks for the Preparation of Nitrogen-Containing Heterocycles

Cited by 325 publications

References 0 publications

Tandem mass spectrometric study of annelation isomers of the novel thieno[3′,2′:4,5]pyrido[2,3-d]pyridazine ring system

Tandem mass spectrometric study of annelation isomers of the novel thieno[3′,2′:4,5]pyrido[2,3-d]pyridazine ring system

Synthesis of stabilized phosphorus ylides from electron-poor alcohols and their applications in the preparation of 2,5-dihydrofuran derivatives

Surpassing Torquoelectronic Effects in Conrotatory Ring Closures: Origins of Stereocontrol in Intramolecular Ketenimine-Imine [2+2] Cycloadditions

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