Facile four-component domino reactions for the synthesis of highly functionalized tetrahydroquinolones

Muthusaravanan, Sivasubramanian; Bala, Balasubramanian Devi; Perumal, S.

doi:10.1016/j.tetlet.2013.07.091

Cited by 16 publications

(5 citation statements)

References 30 publications

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“…H 2 SO 4 , p ‐TSA, organocatalysts such as L ‐proline and iodine gave inferior results under standard conditions even after longer reaction times (Scheme 10). [121] …”

Section: Synthesis Of 14‐dihydropyridine Derivativesmentioning

confidence: 99%

“…Functionalized tetrahydroquinolones through one pot domino approach. [121] multicomponent reactions. [122,123] In 2016, Zhaleh et al used chitosan as a re-usable biocatalyst for the synthesis of different 1,4-dihydropyridine derivatives in good yields.…”

Section: Using Metal Catalystmentioning

confidence: 99%

“…H 2 SO 4 , p-TSA, organocatalysts such as L-proline and iodine gave inferior results under standard conditions even after longer reaction times (Scheme 10). [121] Organo-catalysts proved to be an important metal-free catalyst for the synthesis of heterocyclic compounds through Scheme 5. 1,4-dihydropyridines synthesis using zirconia catalyst.…”

Section: Using Metal Catalystmentioning

confidence: 99%

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Application of Cyclohexane‐1,3‐diones in the Synthesis of Six‐Membered Nitrogen‐Containing Heterocycles

Sharma¹,

Kumar

et al. 2022

ChemistrySelect

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Cyclohexane‐1,3‐dione and its derivatives are imperative precursors in synthetic organic chemistry as they are useful intermediates for the synthesis of a wide range of biologically active natural products, heterocycles and pharmaceuticals. Recently, cyclohexane‐1,3‐diones have been used for the synthesis of varied array of six‐membered nitrogen‐containing heterocycles in the presence of aldehydes, acetoacetic esters, malononitrile, chalcones, coumarins, acetophenones, amino acids, amines, etc. under catalytic and non‐catalytic conditions. Newest studies on the importance of these heterocycles motivated us to compile all the recently developed processes which include the fabrication of six‐membered nitrogen heterocycles. This article is mainly focused on the efficient synthesis of six‐membered N‐heterocycles i. e. 1,4‐dihydropyridine, acridine‐1,8‐diones, benzoacridinones, quinolones and pyridine derivatives from cyclohexane‐1,3‐diones as one of the substrates, published for the last ten years.

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“…H 2 SO 4 , p ‐TSA, organocatalysts such as L ‐proline and iodine gave inferior results under standard conditions even after longer reaction times (Scheme 10). [121] …”

Section: Synthesis Of 14‐dihydropyridine Derivativesmentioning

confidence: 99%

Section: Using Metal Catalystmentioning

confidence: 99%

Section: Using Metal Catalystmentioning

confidence: 99%

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Application of Cyclohexane‐1,3‐diones in the Synthesis of Six‐Membered Nitrogen‐Containing Heterocycles

Sharma¹,

Kumar

et al. 2022

ChemistrySelect

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“…The 1 H NMR analysis on the crude product confirmed that the reaction yielded only single diastereoisomers (Scheme 4). [11] In the synthesis of heterocycles using tertiary enaminones, the work from Perumal et al [12] revealed that replacing the enal component with aryl aldehydes 12 and cyclic 1,3-diketones 13 allowed the one-pot synthesis of 1,4-DHPs 14 via a four-component reaction. The secondary enaminone 6 resulting from transamination and the enone 15 from Knoevenagel condensation were believed to be key intermediates in this reaction (Scheme 5).…”

Section: Reactions Based On Transaminationmentioning

confidence: 99%

Domino Reactions Based on Combinatorial Bond Transformations in Electron-Deficient Tertiary Enamines

Wan

Gao

2016

The Chemical Record

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Electron-deficient enamines such as enaminones and enaminoesters are moieties showing widespread application in organic synthesis. Among the various available electron-deficient enamines, the N,N-disubstituted amino-functionalized ones (tertiary enamines) represent a class of special enamines with distinct properties and important applications. Based on our longstanding interest in exploring novel synthetic methods using electron-deficient tertiary enamines, we present herein the research advances in organic synthesis via domino reactions making use of the combinatorial C-N, C=C, C-H, and other bond transformations of electron-deficient tertiary enamines.

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“…However, it is much more efficient if one can form several bonds in one sequence without isolating the intermediates, changing the reaction conditions, or adding reagents (Tietze & Beifuss, 1993). This type of reaction, commonly termed a domino reaction (Muthusaravanan et al, 2013;Kadzimirsz et al, 2008;Criado et al, 2013) would allow a substantial reduction of waste compared to stepwise reactions. The amount of solvents, reagents, adsorbents, and energy would also be dramatically decreased.…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure of (4-chlorophenyl)[2-(10-hydroxyphenanthren-9-yl)phenanthro[9,10-b]furan-3-yl]methanone

Sajitha

Sithambaresan²,

Jacob

et al. 2014

Acta Cryst E

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In the title compound, C37H21ClO3, the dihedral angle between the two phenanthrene moieties is 57.79 (5)°. The furan and one of the phenanthrene groups are fused in an almost coplanar arrangement [dihedral angle = 5.14 (8)°] and the furan unit makes dihedral angles of 70.27 (11) and 57.58 (8)° with the planes of the phenyl and the second phenanthrene group, respectively. In the crystal, neighbouring molecules are connectedviatwo intermolecular hydrogen-bonding interactions (O—H...O and C—H...O) towards the carbonyl O atom with donor–acceptor distances of 2.824 (2) and 3.277 (3) Å, creating an inversion dimer. A non-classical C—H...Cl interaction [3.564 (2) Å] and three C—H...π interactions, with C...π distances of 3.709 (3), 3.745 (2) and 3.628 (3) Å, connect the molecules, forming a three-dimensional supramolecular architecture in the solid state.

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Facile four-component domino reactions for the synthesis of highly functionalized tetrahydroquinolones

Cited by 16 publications

References 30 publications

Application of Cyclohexane‐1,3‐diones in the Synthesis of Six‐Membered Nitrogen‐Containing Heterocycles

Application of Cyclohexane‐1,3‐diones in the Synthesis of Six‐Membered Nitrogen‐Containing Heterocycles

Domino Reactions Based on Combinatorial Bond Transformations in Electron-Deficient Tertiary Enamines

Crystal structure of (4-chlorophenyl)[2-(10-hydroxyphenanthren-9-yl)phenanthro[9,10-b]furan-3-yl]methanone

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