Titanium‐Catalyzed, One‐Pot Synthesis of 2‐Amino‐3‐cyano‐ pyridines

Dissanayake, Amila A.; Staples, Richard J.; Odom, Aaron L.

doi:10.1002/adsc.201301046

Cited by 33 publications

(9 citation statements)

References 42 publications

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“…The amino acid group can activate the nitrile group for Michael addition of the used nucleophile (IV). Also it can facilitate the cyclization process by nucleophilic addition of the OH group in intermediate V. 38 Finally, a proton exchange and tautomerization resulted in the production of the target molecule (VI).…”

Section: Magnetic Nanoparticle Supported L-cysteine (Lcmnp) Preparati...mentioning

confidence: 99%

l-Cysteine functionalized magnetic nanoparticles (LCMNP): a novel magnetically separable organocatalyst for one-pot synthesis of 2-amino-4H-chromene-3-carbonitriles in water

2015

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In this study, L-cysteine was chemically grafted to magnetic nanoparticles in order to prepare a reusable magnetic material incorporating an amino acid moiety. For this purpose, silica-coated magnetic nanoparticles (Fe3O4@SiO2) were reacted with trimethoxy(vinyl)silane to produce vinyl-functionalized magnetic nanoparticles (VMNP). Reaction of a VMNP substrate with L-cysteine in the presence of azobisisobutyronitrile (AIBN) resulted in the production of L-cysteine-functionalized magnetic nanoparticles (LCMNP). The LCMNP material was characterized using different microscopy and spectroscopy techniques such as FT-IR, XRD, TEM, SEM, EDX, VSM, and elemental analysis. Also, LCMNP was analyzed by thermogravimetric analysis (TGA) in order to determine its thermal behavior. The applicability of the LCMNP material was evaluated in a three-component coupling reaction between a nucleophile, salicylaldehyde and malononitrile as the catalyst for one-pot synthesis of 2-amino-4H-chromene-3-carbonitrile derivatives. The catalyst system showed high catalytic activity in this process and target products were obtained in high isolated yields in water as a green solvent. The LCMNP catalyst was reusable in this reaction at least 7 times with no significant decrease in its catalytic activity.

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Section: Magnetic Nanoparticle Supported L-cysteine (Lcmnp) Preparati...mentioning

confidence: 99%

l-Cysteine functionalized magnetic nanoparticles (LCMNP): a novel magnetically separable organocatalyst for one-pot synthesis of 2-amino-4H-chromene-3-carbonitriles in water

2015

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“…The catalyst’s ability to successfully produce modest yields of the 3CC products is significant. While there does appear to be a steric demand that limits the choice of amine to ortho-substituted anilines, this catalyst still provides a route to a versatile organic building block. − ,− These results suggest that further examination of surface-bound titanium species may provide the substrate scope, tolerance, and surface stability needed to achieve a reusable and selective titanium catalyst for multicomponent couplings.…”

Section: Discussionmentioning

confidence: 99%

Titanium-Catalyzed Hydroamination and Multicomponent Coupling with a Simple Silica-Supported Catalyst

Aldrich

Odom

2018

Organometallics

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Hydroamination and multicomponent coupling reactions catalyzed by homogeneous Ti(IV) complexes can produce valuable imines, amines, and other nitrogencontaining organic building blocks. Typically catalysts for this transformation are very sensitive to ancillary ligand design and often suffer from catalyst deactivation, necessitating use in a single reaction. Here, we have attempted to address these issues by moving toward a solid-supported Ti catalyst active for these reaction types. We present initial results to synthesize and probe the catalytic reactivity of silica-supported titanium amide precatalysts. With minimal treatment of commercially available fumed silica, Ti(NMe 2 ) 2 /SiO 2 200 can be isolated upon addition of Ti(NMe 2 ) 4 . This species gives high yields and high regioselectivity for hydroamination of a variety of alkynes with anilines. The solid-supported species is also an active catalyst for the formation of tautomers of unsymmetrical 1,3-diimines via three-component coupling of bulky anilines, alkynes, and isonitriles. Reusability and possible catalyst deactivation pathways are also discussed.

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“…28 , top). 122 Additionally, CAT16 -catalyzed hydroamination of alkynes with silylamines regioselectively forms reactive N -silylenamines ( IM50 ), which can undergo subsequent reaction with α,β-unsaturated carbonyls to yield tri-, tetra-, or pentasubstituted pyridines ( 63 ) upon oxidation ( Fig. 28 , bottom).…”

Section: -Membered Heterocyclesmentioning

confidence: 99%

Multicomponent syntheses of 5- and 6-membered aromatic heterocycles using group 4–8 transition metal catalysts

et al. 2021

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Titanium‐Catalyzed, One‐Pot Synthesis of 2‐Amino‐3‐cyano‐ pyridines

Cited by 33 publications

References 42 publications

l-Cysteine functionalized magnetic nanoparticles (LCMNP): a novel magnetically separable organocatalyst for one-pot synthesis of 2-amino-4H-chromene-3-carbonitriles in water

l-Cysteine functionalized magnetic nanoparticles (LCMNP): a novel magnetically separable organocatalyst for one-pot synthesis of 2-amino-4H-chromene-3-carbonitriles in water

Titanium-Catalyzed Hydroamination and Multicomponent Coupling with a Simple Silica-Supported Catalyst

Multicomponent syntheses of 5- and 6-membered aromatic heterocycles using group 4–8 transition metal catalysts

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