Green synthetic approach toward new chromeno[4,3-b]quinoline and chromeno[4,3-b]pyridine derivatives

Olyaei, Abolfazl; Ebrahimi, Reyhaneh Mohammad; Adl, Alireza; Sadeghpour, Mahdieh

doi:10.1007/s10593-019-02585-4

Cited by 19 publications

(11 citation statements)

References 25 publications

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“…Synthesis of symmetrical and unsymmetrical bis-chromeno [4,3b]quinolin-6-one from dialdehyde . [44] [26] Scheme 22. Synthesis of chromeno-quinolines under oxygen atmosphere.…”

Section: The Synthesis Of Chromeno-quinoline Derivatives Via Single-s...mentioning

confidence: 99%

“…An organocatalyst based synthesis of chromeno[4,3b]quinolines 31 and chromeno[4,3-b]pyridine derivatives 32 has been described by Olyaei et alvia a facile one-pot three component methodology. [26] Guanidine hydrochloride was used as the organocatalyst. The mixture of aromatic aldehydes and 4-amino coumarins were allowed to react with dimedone in water or with meldrum's acid in ethanol separately.…”

Section: Chemistryselectmentioning

confidence: 99%

“…A diverse range of efficient strategies are available in the literature including both transition-metal catalyzed [25] and transition metal-free pathway. [26] Among transition metals, copper [27] and palladium [28] have often been used. Some examples of gold, [10] silver, [29] ytterbium [23] and other metal [30][31] catalysts are also available.…”

Section: Introductionmentioning

confidence: 99%

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Recent Advances on Synthesis of Fused Chromeno‐Quinoline Heterocycles under Transition Metal‐Free Condition

Mal

Jana

2022

ChemistrySelect

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Among the various other organic compounds, the compounds having heterocyclic core are extensively circulated in nature and are often crucial for life. The concerned heterocyle may or may not be aromatic. They often show a variety of physiological, industrial and also theoretical significance. Quinoline derivatives are very popular anti-biotics and benzopyran or chromenes is another important heterocyclic moiety found widely in naturally occurring plant products like fruits and vegetables. However, when chromene and quinoline are present in a molecule in fused form, a subclass of very important bio-active chromene-fused quinoline heterocycles is formed. This review covers recent reports on transition metalfree synthesis of chromeno-quinoline derivatives in short and hassle-free reaction protocols.

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“…Synthesis of symmetrical and unsymmetrical bis-chromeno [4,3b]quinolin-6-one from dialdehyde . [44] [26] Scheme 22. Synthesis of chromeno-quinolines under oxygen atmosphere.…”

Section: The Synthesis Of Chromeno-quinoline Derivatives Via Single-s...mentioning

confidence: 99%

Section: Chemistryselectmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Recent Advances on Synthesis of Fused Chromeno‐Quinoline Heterocycles under Transition Metal‐Free Condition

Mal

Jana

2022

ChemistrySelect

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“…The synthesis of chromeno [4,3-b]quinoline-6,8(9H)dione derivatives have been reported by multicomponent reactions. [35][36][37][38][39][40] Chromeno [4,3-b]quinoline-6,8(9H)-diones are Scheme 1. Starch/SPION@SO 3 H catalyzed synthesis of chromeno [4,3-b]quinoline-6,8(9H)-dione derivatives.…”

Section: Introductionmentioning

confidence: 99%

“…The synthesis of chromeno[4,3‐ b ]quinoline‐6,8(9 H )‐dione derivatives have been reported by multicomponent reactions. [ 35–40 ] Chromeno[4,3‐ b ]quinoline‐6,8(9 H )‐diones are significant, due to the vast biological activities, including cytotoxic activity. [ 41,42 ]…”

Section: Introductionmentioning

confidence: 99%

Sulfonic Acid Functionalized Magnetic Starch as an Efficient Catalyst for the Synthesis of Chromeno[4,3‐b]quinoline‐6,8(9H)‐dione Derivatives

et al. 2021

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In this paper, sulfonic acid functionalize magnetic starch (denoted Starch/SPION@SO3H) is fabricated by the polymerization of 4‐styrenesulfonic acid on the surface of magnetic starch. Magnetic starch (Starch/SPION) is synthesized by covalent modification of starch by silica capsulate superparamagnetic iron oxide nanoparticles (SPION). For this purpose, Starch/SPION is modified by allyltrimethoxysilane, follows by the polymerization of 4‐styrenesulfonic acid onto this material. The catalyst is characterized by various characterization techniques, including transmission electron microscopy (TEM), high resolution transmission electron microscopy (HRTEM), thermogravimetric analysis (TGA), vibrating‐sample magnetometer (VSM), X‐ray photoelectron spectroscopy (XPS), and acid/base titration. The characterizations prove the structure of Starch/SPION@SO3H catalyst. The catalytic activity of Starch/SPION@SO3H is evaluated in the multicomponent reaction of 4‐hydroxycoumarin, benzaldehydes, dimedone, and ammonium acetate for the synthesis of chromeno[4,3‐b]quinoline‐6,8(9H)‐dione derivatives. The catalyst shows very good activity in the synthesis of chromeno[4,3‐b]quinoline‐6,8(9H)‐dione derivatives. Several benzaldehydes with electron donating or electron withdrawing functionalities are used as starting material and all the substrates give the desired products in high isolated yields. In addition, the catalyst is extremely reusable during 10 sequential runs. Characterization of Starch/SPION@SO3H catalyst by TEM, VSM, and acid/base titration after recovery from the reaction proves the stability of the catalyst in the reaction conditions.

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A novel magnetic layered double hydroxide as potent mesoporous recyclable heterogeneous nanocatalyst for the synthesis of 1H‐chromeno[2,3‐b]pyridine‐3‐carbonitrile derivatives

Ghobakhloo

Azarifar

Ghaemi

2021

Applied Organom Chemis

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A magnetically separable cobalt complex of macrocyclic pseudo-crown ether (PCE) immobilized on magnetic Cu/Al-layered double hydroxide (γ-Fe 2 O 3 @Cu 3 Al-layered double hydroxide (LDH)/PCE-Co) was readily fabricated using a simple four-step postsynthetic modification strategy. This newly prepared nanocomposite was characterized by different chemo-physical approaches, including Fourier transform infrared (FT-IR), scanning electron microscopy (SEM), transmission electron microscopy (TEM), inductively coupled plasma optical emission spectroscopy (ICP-OES), vibrating sample magnetometer (VSM), X-ray diffraction (XRD), nitrogen adsorptiondesorption isotherms, energy-dispersive X-ray spectroscopy (EDX), and elemental mapping. The catalytic performance of these nanoparticles (NPs) was explored in the synthesis of diverse 1H-chromeno[2,3-b]pyridine-3-carbonitrile derivatives via one-pot three-component reactions under green reaction conditions. Environmentally benign reaction conditions, simple separation, high yields of the reactions, versatility, easy magnetic separation, and reusability for several runs without significant loss of catalytic performance are the key advantages that make this protocol an ideal alternative method for the synthesis of chromene derivatives.

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Green synthetic approach toward new chromeno[4,3-b]quinoline and chromeno[4,3-b]pyridine derivatives

Cited by 19 publications

References 25 publications

Recent Advances on Synthesis of Fused Chromeno‐Quinoline Heterocycles under Transition Metal‐Free Condition

Recent Advances on Synthesis of Fused Chromeno‐Quinoline Heterocycles under Transition Metal‐Free Condition

Sulfonic Acid Functionalized Magnetic Starch as an Efficient Catalyst for the Synthesis of Chromeno[4,3‐b]quinoline‐6,8(9H)‐dione Derivatives

A novel magnetic layered double hydroxide as potent mesoporous recyclable heterogeneous nanocatalyst for the synthesis of 1H‐chromeno[2,3‐b]pyridine‐3‐carbonitrile derivatives

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