One-pot reductive N-vinylation and C(4)-phosphorylation of pyridines with alkyl propiolates and secondary phosphine chalcogenides

Гусарова, Н. К.; Volkov, Pavel А.; Иванова, Н. И.; Arbuzova, S. N.; Khrapova, Kseniya O.; Albanov, A. I.; Смирнов, В. И.; Bоrodinа, Tatyana N.; Трофимов, Б. А.

doi:10.1016/j.tetlet.2015.06.062

Cited by 19 publications

(6 citation statements)

References 42 publications

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“…2-Methylpyridine 1c with methyl propiolate 11a and diphenylphosphine sulfide 2e gave dihydropyridine 12g in a 47% yield, along with Eand Z-isomers of diphenyl (methylpropenoate)phosphine sulfide 13 (content in the reaction mixture ≈ 30%, identified by 31 P NMR) (Scheme 10) [45]. The side formation of vinylphosphine sulfide 13 was expected from the known data that secondary phosphine chalcogenides added to acyl-and cyanoacetylenes in the presence of the base [54].…”

Section: N-vinylated/c-phosphorylated Pyridines: Delayed S N H Phosphorylationmentioning

confidence: 88%

“…This was rationalized [37] by (i) the steric repulsion between pyridine hydrogen in position 6sixand aromatic substituent of the internal acetylene; (ii) the formation of a benzyl-like cationic intermediate; (iii) the generation of stable chalcones. Therefore, as shown above, in certain cases, the three-component reaction can be affected (delayed on the kinetic step) using terminal electron-deficient acetylenes [39,[45][46][47][48].…”

Section: N-vinylated/c-phosphorylated Pyridines: Delayed S N H Phosphorylationmentioning

confidence: 98%

“…The synthesis of N-vinylated/C(4)-phosphorylated 1,4-dihydropyridines 12a-r in a 47-90% yield from pyridines 1, alkyl propiolates 11 and secondary phosphine chalcogenides 2 was implemented as a one-pot three-component reaction at 20-52 • C for 3-20 h (Scheme 9) [45,47]. The reactions involving pyridine 1a and secondary phosphine sulfide 2f or selenide 2i proceeded at room temperature, though phosphine oxide 2a required slight heating (50-52 • C), likely due to its lower acidity.…”

Section: N-vinylated/c-phosphorylated Pyridines: Delayed S N H Phosphorylationmentioning

confidence: 99%

“…A short time ago [37][38][39][40], the nucleophilic substitution of hydrogen (S N H reaction) in non-activated pyridines and their fused derivatives by secondary phosphine chalcogenides (synthesized from red phosphorus [41][42][43][44]) in the presence of electron-deficient terminal and internal acetylenes was disclosed. These reactions involve the step of N-vinylation/ C-phosphorylation of pyridinoids, and are often retained at this step [45][46][47][48][49]. Afterwards, a series of this finding's follow-up works appeared.…”

Section: Introductionmentioning

confidence: 99%

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Electron-Deficient Acetylenes as Three-Modal Adjuvants in SNH Reaction of Pyridinoids with Phosphorus Nucleophiles

2021

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Publications covering a new easy metal-free functionalization of pyridinoids (pyridines, quinolines, isoquinolines, acridine) under the action of the system of electron-deficient acetylenes (acetylenecarboxylic acid esters, acylacetylenes)/P-nucleophiles (phosphine chalcogenides, H-phosphonates) are reviewed. Special attention is focused on a SNH reaction of the regioselective cross-coupling of pyridines with secondary phosphine chalcogenides triggered by acylacetylenes to give 4-chalcogenophosphorylpyridines. In these processes, acetylenes act as three-modal adjuvants (i) activating the pyridine ring towards P-nucleophiles, (ii) deprotonating the P-H bond and (iii) facilitating the nucleophilic addition of the P-centered anion to a heterocyclic moiety followed by the release of the selectively reduced acetylenes (E-alkenes).

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Section: N-vinylated/c-phosphorylated Pyridines: Delayed S N H Phosphorylationmentioning

confidence: 88%

Section: N-vinylated/c-phosphorylated Pyridines: Delayed S N H Phosphorylationmentioning

confidence: 98%

Section: N-vinylated/c-phosphorylated Pyridines: Delayed S N H Phosphorylationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Electron-Deficient Acetylenes as Three-Modal Adjuvants in SNH Reaction of Pyridinoids with Phosphorus Nucleophiles

2021

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“…With a similar concept, they found that phosphorylated N ‐vinyl‐1,4‐dihydropyridines 315 could be prepared via a three‐component reaction of 2‐substituted pyridines 313 , alkyl propiolates and secondary phosphine chalcogenides (Scheme ) …”

Section: Direct Phosphorylation Of the Parent Heterocyclesmentioning

confidence: 99%

Recent Advances in the Construction of Phosphorus‐Substituted Heterocycles, 2009–2019

2020

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Scheme 20. Phosphonation of pyridinones.Scheme 21. CuI-catalyzed phosphoramidate formation.Scheme22. Phosphonation of coumarin and quinolinone.Scheme23. Silver(I)-catalyzed phosphonation of coumarins. Scheme 33. Electrochemical C(sp 2 )ÀHphosphonation of quinoxaline-2(1H)-ones. Scheme 39. Phosphorylation of quinoxaline-2(1 H)-ones. Scheme40. Autoxidative phosphorylation of quinoxalines. Scheme 41. DTBP-mediated formation of phosphonated benzothiazoles. Scheme42. Phosphonation of imidazole[2,1-b]thiazoles.Scheme 47. Copper(I)-catalyzedp hosphonationo fN-iminoisoquinolinium ylides. Scheme48. Aerobic phosphonationofC ( sp 3 ) À Hbonds. Scheme 49. Copper(II)/PBQ-catalyzed phosphorylation of 3,4-dihydro-1,4-benzoxazin-2-ones. Scheme 87. Asymmetric exo-selective [3+ +2] cycloaddition to afford phosphorus-substituted pyrrolidines. Scheme 95. Cascade condensation/cyclization to phosphonylated thienopyridines. Scheme 96. S N Ar'-involved cascade reactions to phosphonylated oxygenorn itrogen heterocycles.Scheme 97. Manganese(III)-mediated synthesis of 3-phosphonyldihydrofuransfrom b-ketophosphonates.Scheme98. Cyclization to phosphonated isochromenes.Scheme 121. Asymmetric [4+ +2] cycloaddition of b,g-unsaturated a-ketophosphonates.

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ChemInform Abstract: One‐Pot Reductive N‐Vinylation and C(4)‐Phosphorylation of Pyridines with Alkylpropiolates and Secondary Phosphine Chalcogenides.

et al. 2015

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One-Pot Reductive N-Vinylation and C(4)-Phosphorylation of Pyridines with Alkylpropiolates and Secondary Phosphine Chalcogenides. -The title reaction proceeds under mild conditions to form the corresponding products with high regioand stereoselectivity. -(GUSAROVA, N. K.; VOLKOV, P. A.; IVANOVA, N. I.; ARBUZOVA, S. N.; KHRAPOVA, K. O.; ALBANOV, A. I.; SMIRNOV, V. I.; BORODINA, T. N.; TROFIMOV*, B. A.; Tetrahedron Lett. 56 (2015) 33, 4804-4806, http://dx.

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One-pot reductive N-vinylation and C(4)-phosphorylation of pyridines with alkyl propiolates and secondary phosphine chalcogenides

Cited by 19 publications

References 42 publications

Electron-Deficient Acetylenes as Three-Modal Adjuvants in SNH Reaction of Pyridinoids with Phosphorus Nucleophiles

Electron-Deficient Acetylenes as Three-Modal Adjuvants in SNH Reaction of Pyridinoids with Phosphorus Nucleophiles

Recent Advances in the Construction of Phosphorus‐Substituted Heterocycles, 2009–2019

ChemInform Abstract: One‐Pot Reductive N‐Vinylation and C(4)‐Phosphorylation of Pyridines with Alkylpropiolates and Secondary Phosphine Chalcogenides.

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