Tandem reactions of 6-phenylethynylpyrimidine-5-carbaldehydes with alcohols: regioselective synthesis of 5-alkoxy-(7Z)-7-benzylidene-5,7-dihydrofuro[3,4-d]pyrimidines and 5-alkoxy-7-phenyl-5H-pyrano[4,3-d]pyrimidines

Čikotienė, Inga; Bukšnaitienė, Rita; Rudys, Simonas; Morkunas, Marius; Motiejaitis, Dainius

doi:10.1016/j.tet.2009.10.108

Cited by 14 publications

(2 citation statements)

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“…Cikotiene et al . have established a novel and productive procedure for the synthesis of pyrano[4,3‐ d ]pyrimidine 117 backbones through silver catalysis [66] . 4‐Dialkylamino‐6‐phenylethynyl pyrimidine‐5‐carbaldehydes 116 and alcohols 71 were the starting substrates employed (Scheme 66).…”

Section: Six Membered Heterocycles With One Heteroatommentioning

confidence: 99%

An Overview of Ag‐catalyzed Synthesis of Six‐membered Heterocycles

et al. 2020

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Heterocyclic chemistry is an immensely expanding field in organic synthesis owing to its potency in various disciplines like natural products chemistry, pharmaceuticals, drug discovery and industry. Silver catalysis has gained much attraction in recent years mainly in the scenario of heterocyclic synthesis. Among heterocycles, the six membered heterocycles are the most popular and widely applied in various fields. This review discusses on the investigations on various silver‐catalyzed synthesis of six‐membered heterocycles and covers literatures up to 2020.

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Section: Six Membered Heterocycles With One Heteroatommentioning

confidence: 99%

An Overview of Ag‐catalyzed Synthesis of Six‐membered Heterocycles

et al. 2020

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“…Several metal ions, such as Pd(II), Cu(I), Ag(I), Au(I), and In(III) salts, have been used as catalysts for the synthesis of isochromenes and analogues following this approach. An enantioselective version of this reaction, catalyzed by chiral gold acyclic diaminocarbene (ADC) complexes has also been reported .…”

Section: Introductionmentioning

confidence: 99%

Mild Regiospecific Synthesis of 1-Alkoxy-isochromenes Catalyzed by Well-Defined [Silver(I)(Pyridine-Containing Ligand)] Complexes

et al. 2014

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The synthesis of 3-substituted-1-alkoxyisochromenes starting from 2-alkynylbenzaldehydes and different alcohols is reported. The reaction is catalyzed by a silver(I) complex with an original macrocyclic pyridine-containing ligand. The approach is characterized by absolute regioselectivity, mild reaction conditions, good to excellent reaction yields, cleanness of the reaction, and reduced purification steps. The reaction mechanism was investigated by in-depth (1)H NMR experiments and an aimed "trapping" experiment.

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Study on the Reactions of Acetylenic Aldehydes with Dimethyl Phosphite in Basic Media: Phosphonate‐Phosphate Rearrangement versus 5‐exo‐dig Cyclization Reactions

Čikotienė

Bukšnaitienė

2012

Adv Synth Catal

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Tandem reactions of various acetylenic aldehydes with dimethyl phosphite in basic media were investigated. It was shown that in the case of a non-activated triple bond of the starting materials, the well-known Pudovik reaction followed by a subsequent phosphonate-phosphate rearrangement took place. On the other hand when the triple bond of the starting materials is activated by electron-withdrawing heterocycles, a smooth and regioselective tandem 5-exo-dig cyclization reactions becomes possible.

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Tandem reactions of 6-phenylethynylpyrimidine-5-carbaldehydes with alcohols: regioselective synthesis of 5-alkoxy-(7Z)-7-benzylidene-5,7-dihydrofuro[3,4-d]pyrimidines and 5-alkoxy-7-phenyl-5H-pyrano[4,3-d]pyrimidines

Cited by 14 publications

References 16 publications

An Overview of Ag‐catalyzed Synthesis of Six‐membered Heterocycles

An Overview of Ag‐catalyzed Synthesis of Six‐membered Heterocycles

Mild Regiospecific Synthesis of 1-Alkoxy-isochromenes Catalyzed by Well-Defined [Silver(I)(Pyridine-Containing Ligand)] Complexes

Study on the Reactions of Acetylenic Aldehydes with Dimethyl Phosphite in Basic Media: Phosphonate‐Phosphate Rearrangement versus 5‐exo‐dig Cyclization Reactions

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