Synthesis of alkynyl/alkenyl-substituted pyridine derivatives via heterocyclization and Pd-mediated Sonogashira/Heck coupling process in one-pot: a new MCR strategy

Mohan, Reddy Bodireddy; Reddy, N. C. Gangi; Kumar, Santosh

doi:10.1039/c4ra01053a

Cited by 15 publications

(1 citation statement)

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“…Pyridine derivatives are an important class of N-heterocycles due to their ubiquitous nature in natural products, − active pharmaceuticals, − agrochemicals, , ligands for various metal-catalyzed organic transformations − and materials with photo- or electrochemical properties. − Traditional methods for the synthesis of pyridines involve condensation of amines and carbonyl compounds, metal-catalyzed cycloaddition reactions, and cycloisomerization. − Multicomponent reactions, cross-coupling reactions − and ring-closing metathesis , have all been utilized to access multisubstituted pyridines.…”

Section: Introductionmentioning

confidence: 99%

One-Pot Sequential Hydroamination Protocol for N-Heterocycle Synthesis: One Method To Access Five Different Classes of Tri-Substituted Pyridines

Verma

Schafer

2023

J. Org. Chem.

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Tri-substituted pyridines are important scaffolds that can be found in a plethora of commercially available drugs. A one-pot general method for the selective synthesis of less explored/challenging patterns of tri-substituted pyridines is described. Hydroamination of alkynes with commercially available N-triphenylsilylamine generates N-silylenamines. These in situ generated N-silylenamines, upon reaction with α,β-unsaturated carbonyl compounds and subsequent oxidation, furnish 25 examples of selectively substituted 2,4,5-, 2,3,4-, 3,4,5-, 2,3,5-, and 2,3,6-trisubstituted pyridines in up to 78% yield. The reaction features high functional group compatibility providing an expeditious and general approach for the assembly of selectively substituted tri-substituted pyridine derivatives. The robustness and practicality of the reaction have been demonstrated in a gram-scale reaction.

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Section: Introductionmentioning

confidence: 99%

One-Pot Sequential Hydroamination Protocol for N-Heterocycle Synthesis: One Method To Access Five Different Classes of Tri-Substituted Pyridines

Verma

Schafer

2023

J. Org. Chem.

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Fe₃O₄@TiO₂@O₂PO₂(CH₂)NHSO₃H as a novel nanomagnetic catalyst: Application to the preparation of 2‐amino‐4,6‐diphenylnicotinonitriles via anomeric‐based oxidation

Zolfigol

Yarie

2016

Applied Organom Chemis

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A new, green and reusable nanomagnetic heterogeneous catalyst, namely Fe 3 O 4 @TiO 2 @O 2 PO 2 (CH 2 )NHSO 3 H, was synthesized and fully characterized using suitable techniques such as infrared spectroscopy, X-ray diffraction, scanning and transmission electron microscopies, thermogravimetry, vibrating sample magnetometry and energy-dispersive X-ray spectroscopy. The applicability of the constructed heterogeneous core-shell catalyst as a promoter was successfully explored for the synthesis of 2-amino-4,6-diphenylnicotinonitrile derivatives upon the reaction of a good range of aromatic aldehydes, acetophenone derivatives, malononitrile and ammonium acetate. The desired products were obtained with good to high yields in short reaction times under solvent-free conditions. The suggested mechanism offers an anomeric-based oxidation route to the products in the final step of the synthetic pathway. KEYWORDS 2-amino-4,6-diphenylnicotinonitriles, anomeric-based oxidation, Fe 3 O 4 @TiO 2 @O 2 PO 2 (CH 2 )NHSO 3 H, nanomagnetic heterogeneous catalyst, solvent-free and benign conditions

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ChemInform Abstract: Synthesis of Alkynyl/Alkenyl‐Substituted Pyridine Derivatives via Heterocyclization and Pd‐Mediated Sonogashira/Heck Coupling Process in One‐Pot: A New MCR Strategy.

2014

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Synthesis of alkynyl/alkenyl-substituted pyridine derivatives via heterocyclization and Pd-mediated Sonogashira/Heck coupling process in one-pot: a new MCR strategy

Abstract: The present MCR strategy opens new avenues in the development of i) a diversity-oriented new cyanopyridine based compound library and ii) new chemical entities other than the present reported molecules.

Cited by 15 publications

References 45 publications

One-Pot Sequential Hydroamination Protocol for N-Heterocycle Synthesis: One Method To Access Five Different Classes of Tri-Substituted Pyridines

One-Pot Sequential Hydroamination Protocol for N-Heterocycle Synthesis: One Method To Access Five Different Classes of Tri-Substituted Pyridines

Fe₃O₄@TiO₂@O₂PO₂(CH₂)NHSO₃H as a novel nanomagnetic catalyst: Application to the preparation of 2‐amino‐4,6‐diphenylnicotinonitriles via anomeric‐based oxidation

ChemInform Abstract: Synthesis of Alkynyl/Alkenyl‐Substituted Pyridine Derivatives via Heterocyclization and Pd‐Mediated Sonogashira/Heck Coupling Process in One‐Pot: A New MCR Strategy.

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Synthesis of alkynyl/alkenyl-substituted pyridine derivatives via heterocyclization and Pd-mediated Sonogashira/Heck coupling process in one-pot: a new MCR strategy

Abstract: The present MCR strategy opens new avenues in the development of i) a diversity-oriented new cyanopyridine based compound library and ii) new chemical entities other than the present reported molecules.

Cited by 15 publications

References 45 publications

One-Pot Sequential Hydroamination Protocol for N-Heterocycle Synthesis: One Method To Access Five Different Classes of Tri-Substituted Pyridines

One-Pot Sequential Hydroamination Protocol for N-Heterocycle Synthesis: One Method To Access Five Different Classes of Tri-Substituted Pyridines

Fe3O4@TiO2@O2PO2(CH2)NHSO3H as a novel nanomagnetic catalyst: Application to the preparation of 2‐amino‐4,6‐diphenylnicotinonitriles via anomeric‐based oxidation

ChemInform Abstract: Synthesis of Alkynyl/Alkenyl‐Substituted Pyridine Derivatives via Heterocyclization and Pd‐Mediated Sonogashira/Heck Coupling Process in One‐Pot: A New MCR Strategy.

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Fe₃O₄@TiO₂@O₂PO₂(CH₂)NHSO₃H as a novel nanomagnetic catalyst: Application to the preparation of 2‐amino‐4,6‐diphenylnicotinonitriles via anomeric‐based oxidation