A new route for the synthesis of 1,3,4-trisubstituted pyrazolo[4,3-c]quinolines via a multicomponent reaction

Alizadeh, Abdolali; Moafi, Leila; Ghanbaripour, Rashid; Abadi, Marziyeh Hossein; Zhu, Zhe; Kubicki, Maciej

doi:10.1016/j.tet.2015.03.062

Cited by 19 publications

(7 citation statements)

References 20 publications

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“…Amongst them, deviations on the bond distances and angles of the N-H and C-H groups were obvious due to the difference in the refining method, and the largest distance between analogous atoms in superimposed molecules was about 0.063 Å. Additionally, the C=O bond lengths were 1.226(2), 1.222(2), and 1.219(2) Å, respectively, due to the strong hydrogen bonds. A simple survey revealed that the related compounds [24][25][26] containing the 3-methoxy-2-thiophenamine fragment often had the intramolecular N-H· · · O hydrogen bond, forming a seven-membered ring. This is a benefit due to the amine and carbonyl groups that are on the same side as thiophene.…”

Section: Crystal Structural Descriptionsmentioning

confidence: 99%

Crystal Structure and Computational Study on Methyl-3-Aminothiophene-2-Carboxylate

et al. 2020

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Methyl-3-aminothiophene-2-carboxylate (matc) is a key intermediate in organic synthesis, medicine, dyes, and pesticides. Single crystal X-ray diffraction analysis reveals that matc crystallizes in the monoclinic crystal system P21/c space group. Three matc molecules in the symmetric unit are crystallographically different and further linked through the N–H⋯O and N–H⋯N hydrogen bond interactions along with weak C–H⋯S and C–H⋯Cg interactions, which is verified by the three-dimensional Hirshfeld surface, two-dimensional fingerprint plot, and reduced density gradient (RDG) analysis. The interaction energies within crystal packing are visualized through dispersion, electrostatic, and total energies using three-dimensional energy-framework analyses. The dispersion energy dominates in crystal packing. To better understand the properties of matc, electrostatic potential (ESP) and frontier molecular orbitals (FMO) were also calculated and discussed. Experimental and calculation results suggested that amino and carboxyl groups can participate in various inter- and intra-interactions.

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Section: Crystal Structural Descriptionsmentioning

confidence: 99%

Crystal Structure and Computational Study on Methyl-3-Aminothiophene-2-Carboxylate

et al. 2020

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“…As we know, 1,3dipolar cycloaddition reaction is an efficient method for the synthesis of pyrazole derivatives. [14] Herein, we started our investigations with the reaction of 4chloro-3-(3-oxo-3-phenylprop-1-en-1-yl)-2H-chromen-2-one 1 a and hydrazonoyl chloride 2 a, in the presence of Et 3 N as base and EtOH at room temperature. The reaction was monitored by TLC, within 8 hours starting materials were consumed completely and compound 3 a was formed.…”

Section: Resultsmentioning

confidence: 99%

Design and Synthesis of Coumarin‐Based Pyrazolopyridines as Biocompatible Fluorescence Dyes for Live‐Cell Imaging

et al. 2020

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An unprecedented strategy for the synthesis of highly fluorescent chromeno[4,3-b]pyrazolo[3,4-d]pyridin-4(3H)-ones via a 1,3-dipolar cycloaddition reaction/ring closure in the presence of NH 4 OAc/air oxidation in a one-pot procedure is described. The molecular structures were characterized by IR spectrophotometry, mass spectrometry, NMR spectroscopy, and single-crystal X-ray analysis. Furthermore, the photophysical properties of synthesized compounds were studied by absorption and fluorescence spectroscopy. All of the compounds exhibited almost similar spectra due to their resembling molecular structures. Therefore, one of the synthesized coumarin-based pyrazolopyridines was selected to evaluate its application as a live-cell imaging agent by an inverted phasecontrast microscope. The result reveals that synthesized chromeno[4,3-b]pyrazolo[3,4-d]pyridin-4(3H)-one has acceptable photostability, low cytotoxicity, satisfactory fluorescence efficiency (Φ f : 0.53), and excellent capability to penetrate into the intracellular space. Accordingly, it can be rendered as a promising dye in fluorescence bioimaging. Chemoselectivity, simple and available starting materials, operational simplicity, and good yields are other outstanding advantages of this reaction.

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“…From the mechanistic point of view, the reaction starts with the condensation of isatin with 1‐aryl‐2‐(1,1,1‐triphenyl‐λ5‐phosphanylidene)‐1‐ethanone, leading to an intermediate which will undergo a 1,3‐dipolar cycloaddition with the in situ formed nitrile imine, generated from the hydrazonoyl chloride in the presence of a base. Subsequent keto‐enol tautomerization and hydroxyl attachment at the C2 position of isatin, leading to intramolecular amide bond cleavage and recyclization, resulting in the final product with the loss of formic acid [274] . 2,3,4‐Trisubstituted quinoline derivatives were also prepared via multicomponent reaction (10 examples), by reacting N ‐unsubstituted isatin‐imines (generated in situ through the reaction of isatin with ammonia) and dialkylacetylenedicarboxylates in methanol, at room temperature (Scheme 134D).…”

Section: Non‐oxindole Derivativesmentioning

confidence: 99%

Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity

Brandão

Marques

Carreiro

et al. 2021

The Chemical Record

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Multicomponent reactions (MCRs) are a valuable tool in diversity‐oriented synthesis. Its application to privileged structures is gaining relevance in the fields of organic and medicinal chemistry. Isatin, due to its unique reactivity, can undergo different MCRs, affording multiple interesting scaffolds, namely oxindole‐derivatives (including spirooxindoles, bis‐oxindoles and 3,3‐disubstituted oxindoles) and even, under certain conditions, ring‐opening reactions occur that leads to other heterocyclic compounds. Over the past few years, new methodologies have been described for the application of this important and easily available starting material in MCRs. In this review, we explore these novelties, displaying them according to the structure of the final products obtained.

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A new route for the synthesis of 1,3,4-trisubstituted pyrazolo[4,3-c]quinolines via a multicomponent reaction

Cited by 19 publications

References 20 publications

Crystal Structure and Computational Study on Methyl-3-Aminothiophene-2-Carboxylate

Crystal Structure and Computational Study on Methyl-3-Aminothiophene-2-Carboxylate

Design and Synthesis of Coumarin‐Based Pyrazolopyridines as Biocompatible Fluorescence Dyes for Live‐Cell Imaging

Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity

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