Ph<sub>3</sub>P promoted one-pot synthesis of dialkyl 2-(2-oxopyridin-1(2<i>H</i>)-yl)but-2-enedioates from a reaction of 2-hydroxypyridine and dialkyl acetylenedicarboxylates

Yavari, Issa; Alborzi, Alireza; Mohtat, Bita

doi:10.3184/030823407x228821

Cited by 15 publications

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“…Yavari and co-workers prepared 2-(2-oxopyridin-1(2 H )-yl)but-2-enedioates through triphenylphosphine-catalyzed addition of 2-hydroxypyridine to dialkyl acetylenedicarboxylates in refluxing chloroform (Scheme ). High yields and moderate regioselectivities were accomplished.…”

Section: Nucleophilic Phosphine Catalysis Of Acetylenesmentioning

confidence: 99%

Phosphine Organocatalysis

et al. 2018

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The hallmark of nucleophilic phosphine catalysis is the initial nucleophilic addition of a phosphine to an electrophilic starting material, producing a reactive zwitterionic intermediate, generally under mild conditions. In this Review, we classify nucleophilic phosphine catalysis reactions in terms of their electrophilic components. In the majority of cases, these electrophiles possess carbon–carbon multiple bonds: alkenes (section 2), allenes (section 3), alkynes (section 4), and Morita–Baylis–Hillman (MBH) alcohol derivatives (MBHADs; section 5). Within each of these sections, the reactions are compiled based on the nature of the second starting material—nucleophiles, dinucleophiles, electrophiles, and electrophile–nucleophiles. Nucleophilic phosphine catalysis reactions that occur via the initial addition to starting materials that do not possess carbon–carbon multiple bonds are collated in section 6. Although not catalytic in the phosphine, the formation of ylides through the nucleophilic addition of phosphines to carbon–carbon multiple bond–containing compounds is intimately related to the catalysis and is discussed in section 7. Finally, section 8 compiles miscellaneous topics, including annulations of the Hüisgen zwitterion, phosphine-mediated reductions, iminophosphorane organocatalysis, and catalytic variants of classical phosphine oxide–generating reactions.

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Section: Nucleophilic Phosphine Catalysis Of Acetylenesmentioning

confidence: 99%

Phosphine Organocatalysis

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“…These are comparable, and in some cases better than those reported for the synthesis of pyrrole derivatives. [6][7][8][9][10][11][12] The procedure described here provides an acceptable method for the preparation of polysubstituted 1H-pyrroles.…”

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Solvent-Free Synthesis of 1,2,3,4-Tetrasubstituted Pyrroles from Enaminones and β-Nitrostyrenes

Yavari

Ghazvini

Aminkhani

2011

Journal of Chemical Research

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A simple synthesis of 1,2,3,4-tetrasubstituted pyrrole derivatives from the reaction of enaminones with β-nitrostyrenes, under solvent-free conditions, is described.Pyrrole and its derivatives are an important class of heterocycles and many naturally occurring pyrroles exhibit bioactivity 1,2 and are used as anti-inflammatory, anti-tumor and immunosuppressive agents. 3,4 Moreover, some pyrroles have found applications in polymer technology. 5 A large number of methods have been developed for synthesis of pyrroles, which include Knorr, Paal-Knorr, and Hantzsch syntheses. 6-10 Enaminones are also employed in several new preparations of pyrrole derivatives. 11,12 As a part of our current studies on the development of new routes in heterocyclic synthesis, 12-16 we now report a convenient and catalyst-free synthesis of 1,2,3,4-tetrasubstituted pyrrole derivatives from the reaction of enaminones with β-nitrostyrenes, under solvent-free conditions (Scheme 1).The reaction of enaminones (1) and β-nitrostyrenes (2) proceeds at room temperature to produce tetrasubstituted pyrroles 3 in moderate to good yields (Scheme 1). The structures of compounds 3 were deduced from their IR, 1 H NMR, and 13 C NMR spectroscopic data. The mass spectra of these compounds displayed molecular ion peaks at appropriate m/z values. The 1 H NMR spectrum of 3a in CDCl 3 showed four singlets for methyl (δ = 2.04 and 2.45 ppm), methylene (δ = 5.08 ppm), and methine (δ = 6.56 ppm) protons, together with a multiplet (δ = 7.10-7.44 ppm) for the phenyl protons. The 13 C NMR spectrum of 3a showed 16 signals in agreement with the proposed structure. Partial assignments of these resonances are given in experimental section. * Correspondent.

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“…One of the classic applications in the chemistry of isocyanides is heterocyclic synthesis. 3,4 As part of our current studies on the development of new routes in heterocyclic synthesis, [5][6][7][8][9] we now report the results of our studies involving the reaction of the zwitterionic intermediates derived from alkyl isocyanides 1 and acetylenic esters 2 with 3-methyl-5,5-diaryl-2-thioxoimidazolidin-4-ones 3, which constitutes a synthesis of dialkyl 2-[(alkylimino) (3methyl-4-oxo-5,5-diaryl-2-thioxoimidazolidin-1-yl) methyl]but-2-enedioates 4 in good yields (Scheme 1).…”

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A One-Pot Synthesis of Functionalised 1-Azadienes Containing 2-Thioxoimidazolidin-4-Ones

Yavari

Ghanbari

Azizian

et al. 2011

Journal of Chemical Research

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Ph₃P promoted one-pot synthesis of dialkyl 2-(2-oxopyridin-1(2H)-yl)but-2-enedioates from a reaction of 2-hydroxypyridine and dialkyl acetylenedicarboxylates

Abstract: 2-Hydroxypyridine undergoes a smooth reaction with dialkyl acetylenedicarboxylates in the presence of triphenylphosphine (15 mol%) to produce the E/Z isomers of dialkyl 2-(2-oxopyridin-1(2H)-yl)but-2-enedioates in high yields.

Cited by 15 publications

References 26 publications

Phosphine Organocatalysis

Phosphine Organocatalysis

Solvent-Free Synthesis of 1,2,3,4-Tetrasubstituted Pyrroles from Enaminones and β-Nitrostyrenes

A One-Pot Synthesis of Functionalised 1-Azadienes Containing 2-Thioxoimidazolidin-4-Ones

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Ph3P promoted one-pot synthesis of dialkyl 2-(2-oxopyridin-1(2H)-yl)but-2-enedioates from a reaction of 2-hydroxypyridine and dialkyl acetylenedicarboxylates

Abstract: 2-Hydroxypyridine undergoes a smooth reaction with dialkyl acetylenedicarboxylates in the presence of triphenylphosphine (15 mol%) to produce the E/Z isomers of dialkyl 2-(2-oxopyridin-1(2H)-yl)but-2-enedioates in high yields.

Cited by 15 publications

References 26 publications

Phosphine Organocatalysis

Phosphine Organocatalysis

Solvent-Free Synthesis of 1,2,3,4-Tetrasubstituted Pyrroles from Enaminones and β-Nitrostyrenes

A One-Pot Synthesis of Functionalised 1-Azadienes Containing 2-Thioxoimidazolidin-4-Ones

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Ph₃P promoted one-pot synthesis of dialkyl 2-(2-oxopyridin-1(2H)-yl)but-2-enedioates from a reaction of 2-hydroxypyridine and dialkyl acetylenedicarboxylates