Facile one-pot synthesis of novel dicyanoanilines fused to dithiane ring via a pseudo-four-component reaction

Abaee, M. Saeed; Ehteshami, Fatemeh; Forghani, Soodabeh; Mojtahedi, Mohammad M.; Hadizadeh, Atefeh

doi:10.1007/s13738-017-1065-5

Cited by 6 publications

(4 citation statements)

References 23 publications

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“…Abaee and co-workers 31 reported the synthesis of a collection of dicyanoanilines fused to a dithiane ring via a facile and efficient reaction among aldehydes 91a–j , 1,3-dithia-5-one ( 92 ), two equivalents of malononitrile ( 93 ) and triethylamine as catalyst. The proposed mechanism is depicted in Scheme 12.…”

Section: Pseudo-four Component Reactionsmentioning

confidence: 99%

Pseudo-multicomponent reactions

et al. 2023

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Section: Pseudo-four Component Reactionsmentioning

confidence: 99%

Pseudo-multicomponent reactions

et al. 2023

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“…Ortho-aminocarbonitriles, comprising an important skeleton in organic synthesis, are a significant class of organic compounds [1,2]. Their derivatives are essential intermediates in various heterocyclic syntheses [3][4][5][6], exhibiting important optical properties [7,8] useful in artificial photosynthetic systems [9]. Such moieties, known as acceptor-donor-acceptor (A-D-A) systems [10], are key intermediates of various bioactive compounds [11].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, X-ray crystal structure, DFT, Hirshfeld surfaces, energy frameworks, and molecular docking analysis of a bicyclic ortho-aminocarbonitrile derivative

et al. 2022

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2-Amino-4-(2, 5-dimethoxyphenyl)-4a,5,6,7-tetrahydronaphthalene-1,3,3(4H)-tricarbonitrile has been synthesized and characterized by conventional spectroscopic techniques (FT-IR and 1H NMR) and the three-dimensional structure elucidated by single crystal X-ray diffraction studies (SC-XRD). It exists in monoclinic crystal system with space group P21/c and lattice parameters: a = 14.641(13) Å, b = 8.653(4) Å, c = 16.609(10) Å, β = 116.34(3)°, and Z = 4. In the crystal packing, molecules are connected through N-H···O and N-H···N intermolecular and intramolecular C-H···O interactions. The N1-H11···N2 interaction results in the formation of a dimer corresponding to R22(12) graph-set motif. The molecular structure has been theoretically optimized by using density functional theory (DFT) with the basis set B3LYP/6-311G (d,p). The optimized bond geometry shows consistency with the SC-XRD data. Besides this, the molecular electrostatic potential (MEP), Mulliken charges, and frontier molecular orbital analysis have been described. The dnorm, shape index, curvedness, crystal voids, 2D fingerprint (FP) plots, and 3D energy frameworks using Hirshfeld surface (HS) studies have also been computed and investigated. The molecular docking studies for 2-amino-4-(2, 5-dimethoxyphenyl)-4a,5,6,7-tetrahydronaphthalene-1,3,3(4H)-tricarbonitrile with DNA gyrase/lanosterol 14α-demethylase suggest that the compound may act as an active antimicrobial drug.

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“…[21] They have also demonstrated wide pharmaceutical, [22] biological, [23] and catalytic properties. [24] The use of ultrasonic chemistry in organic synthesis is well documented, [25,26] and we have several reports employing this technique in our ongoing synthetic programs, [27,28] Recently, we also communicated the synthesis of dicyanoanilines fused to various heterocyclic [29][30][31] and homocyclic [32] structures. On this track, we now present a convenient procedure for the synthesis of novel ferrocenyl substituted dicyanoanilines.…”

Section: Introductionmentioning

confidence: 99%

A divergent procedure for multicomponent synthesis of novel ferrocenyl derivatives of dicyanoanilines and cyanopyridines

Mojtahedi

Hosseinkhany

Abaee

2020

Applied Organom Chemis

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A divergent procedure was developed for multicomponent reaction of ferrocenecarboxaldehyde with malononitrile and various cyclic ketones. Ultrasonic irradiation of 1.0:1.0:2.0 ethanolic mixtures of the reactants produced dicyanoanilines 4 chemoselectively in high yields, while equimolar mixtures of the same reactants in refluxing EtOH solely resulted in four-component formation of cyanopyridines 5. Both series of products are obtained directly by spontaneous precipitation in the reaction mixtures avoiding cumbersome and expensive chromatographic separations.

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Facile one-pot synthesis of novel dicyanoanilines fused to dithiane ring via a pseudo-four-component reaction

Cited by 6 publications

References 23 publications

Pseudo-multicomponent reactions

Pseudo-multicomponent reactions

Synthesis, X-ray crystal structure, DFT, Hirshfeld surfaces, energy frameworks, and molecular docking analysis of a bicyclic ortho-aminocarbonitrile derivative

A divergent procedure for multicomponent synthesis of novel ferrocenyl derivatives of dicyanoanilines and cyanopyridines

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