One-pot synthesis of isoquinoline and related compounds via Cu-mediated tandem cross-coupling and cyclization

Dhara, Shubhendu; Singha, Raju; Nuree, Yasin; Ray, Jayanta K.

doi:10.1016/j.tetlet.2013.11.088

Cited by 24 publications

(8 citation statements)

References 17 publications

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“…When the reaction was performed in the absence of ammonia, the dimer 2aa of phenyl acetylene ( 2 a ) was obtained as the major product and unreacted compound 1 a was recovered in 80% from the reaction mixture (Scheme a, (i)). On the other hand, the reaction of 1 a with aqueous ammonia in the presence of CuI (20 mol %) and Zn(OTf) 2 (20 mol %) in DMSO resulted in (2‐bromo‐1‐methyl‐1 H ‐indol‐3‐yl)methanimine ( 4 a ) in 30% yield (Scheme (ii)). Reports of Cu‐catalyzed direct amination of aryl/heteroaryl bromides under similar conditions have been documented previously,, however, in our case the formation of 2‐amino‐1‐methyl‐1 H ‐indole‐3‐carbaldehyde ( 5 a ) was not observed.…”

Section: Resultssupporting

confidence: 82%

Copper-Catalyzed Tandem Imine Formation, Sonogashira Coupling and Intramolecular Hydroamination: A Facile Synthesis of 3-Aryl-γ−carbolines

et al. 2017

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A one‐pot, atom‐economical multicomponent reaction of 2‐bromoindole‐3‐carbaldehydes, alkynes and ammonia was developed in the presence of copper catalyst for the synthesis of a series of 3‐aryl‐γ−carboline derivatives in good to high yields. The developed reaction involved formation of imine followed by copper‐catalyzed directed Sonogashira coupling and intramolecular hydroamination sequence of reactions. This multicomponent approach features mild reaction conditions and good functional group tolerance to access variety of 3‐aryl γ‐carbolines.

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Section: Resultssupporting

confidence: 82%

Copper-Catalyzed Tandem Imine Formation, Sonogashira Coupling and Intramolecular Hydroamination: A Facile Synthesis of 3-Aryl-γ−carbolines

et al. 2017

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“…37 Ligand L2 was synthesized by a copper(I)-mediated cyclization reaction from 2-bromobenzaldehyde and ethynylbenzene. 38 Ligands L3 and L4 were purchased from Alfa Aesar and used as received. Ligands L5−L7 were synthesized by Stille coupling reactions from 1bromonaphthalene, 2-bromonaphthalene, and 9-bromophenanthrene, respectively.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…The diimine ligand 2-(pyridin-2-yl)quinoline (N^N ligand) and C^N ligands L1 and L8 – L10 were synthesized by a Friedländer condensation reaction according to or by modification of the literature procedure. − 3-Aminonaphthalene-2-carboxaldehyde was prepared according to the reported method . Ligand L2 was synthesized by a copper(I)-mediated cyclization reaction from 2-bromobenzaldehyde and ethynylbenzene . Ligands L3 and L4 were purchased from Alfa Aesar and used as received.…”

Section: Experimental Sectionmentioning

confidence: 99%

Effects of Varying the Benzannulation Site and π Conjugation of the Cyclometalating Ligand on the Photophysics and Reverse Saturable Absorption of Monocationic Iridium(III) Complexes

et al. 2018

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A series of monocationic iridium(III) complexes, [Ir(C^N) 2 (pqu)] + PF 6 − [pqu = 2-(pyridin-2-yl)quinoline, C^N = 2-phenylquinoline (1), 3-phenylisoquinoline (2), 1-phenylisoquinoline (3), benzo[h]quinoline (4), 2-(pyridin-2-yl)naphthalene (5), 1-(pyridin-2-yl)naphthalene ( 6), 2-(phenanthren-9-yl)pyridine ( 7), 2-phenylbenzo[g]quinoline (8), 2-(napht ha l e n -2 -y l )q u i n o l i n e ( 9 ) , a n d 2 -( n a p h t h a l e n -2yl)benzo[g]quinoline (10)], were synthesized in this work. These complexes bear C^N ligands with varied degrees of π conjugation and sites of benzannulation, allowing for elucidation of the effects of the benzannulation site at the C^N ligand on the photophysics of the complexes. Ultraviolet−visible (UV−vis) absorption and emission of the complexes were systematically investigated via spectroscopic techniques and time-dependent density functional theory calculations. Their triplet excited-state absorption and reverse saturable absorption (RSA) were studied by nanosecond transient absorption (TA) spectroscopy and nonlinear transmission techniques. The fusion of phenyl ring(s) to the phenyl ring or the 4 and 5 positions of the pyridyl ring of the C^N ligand resulted in red-shifted UV−vis absorption and emission spectra in complexes 2, 5−7, 9, and 10 compared to those of the parent complex 0, while their triplet lifetimes and emission quantum yields were significantly reduced. In contrast, the fusion of one phenyl ring to the other sites of the pyridyl group of the C^N ligand showed an insignificant impact on the energies of the lowest singlet (S 1 ) and triplet (T 1 ) excited states in complexes 1, 3, and 4 but noticeably affected their TA spectral features. The fusion of the naphthyl group to the 5 and 6 and positions at the pyridyl ring did not influence the S 1 energy of complex 8 but altered the nature of the T 1 states in 8 and 10 by switching them to the benzo[g]quinoline-localized 3 π,π* state, which resulted in completely different emission and TA spectra in these two complexes. The site-dependent variations of the ground-and excited-state absorption induced strong but varied RSA from these complexes for 4.1-ns laser pulses at 532 nm, with the RSA strength decreasing in the trend of 3 > 7 ≈ 4 ≈ 9 ≈ 6 > 8 ≈ 1 ≈ 2 ≈ 5 > 10.

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“…41 Another interesting one pot method for the synthesis of biologically active nitrogen heterocycles like isoquinoline and pyridine was developed by Ray et al employing 1,10-phenanthroline as the ligand. 54 Here the reaction between terminal alkyne and substituted aromatic o-bromoaldehyde afforded isoquinoline derivatives as the product while the reaction between terminal alkynes and non aromatic b-bromoaldehyde gave pyridines and dihydro isoquinoline derivatives (Scheme 33).…”

Section: Applicationsmentioning

confidence: 99%

Recent advances and perspectives in copper-catalyzed Sonogashira coupling reactions

2014

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One-pot synthesis of isoquinoline and related compounds via Cu-mediated tandem cross-coupling and cyclization

Cited by 24 publications

References 17 publications

Copper-Catalyzed Tandem Imine Formation, Sonogashira Coupling and Intramolecular Hydroamination: A Facile Synthesis of 3-Aryl-γ−carbolines

Copper-Catalyzed Tandem Imine Formation, Sonogashira Coupling and Intramolecular Hydroamination: A Facile Synthesis of 3-Aryl-γ−carbolines

Effects of Varying the Benzannulation Site and π Conjugation of the Cyclometalating Ligand on the Photophysics and Reverse Saturable Absorption of Monocationic Iridium(III) Complexes

Recent advances and perspectives in copper-catalyzed Sonogashira coupling reactions

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