Mild and green synthesis of tetrahydrobenzopyran, pyranopyrimidinone and polyhydroquinoline derivatives and DFT study on product structures

Bodaghifard, Mohammad Ali; Solimannejad, Mohammad; Asadbegi, Sajad; Dolatabadifarahani, Samira

doi:10.1007/s11164-015-2079-1

Cited by 69 publications

(10 citation statements)

References 29 publications

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“…Several methods for synthesizing tetrahydrobenzo[ b ]pyran scaffolds with MCRs in the presence of various catalysts have been published. For example, CaHPO 4 ( Bodaghifard et al, 2016 ), SiO 2 NPs ( Banerjee et al, 2011 ), ethylenediamine diacetate ( Zhou et al, 2017 ), silica-bonded N-propylpiperazine sodium n-propionate ( Niknam et al, 2013 ), I 2 ( Bhosale et al, 2007 ), NH 4 Al(SO 4 ) 2 .12H 2 O ( Mohammadi et al, 2017 ), NH 4 H 2 PO 4 /Al 2 O 3 ( Maleki and Sedigh Ashrafi, 2014 ), ACoPc-MNPs ( Zolfigol et al, 2016 ), ZnO NPs ( Banerjee and Saha, 2013 ), Fe 3 O 4 @SiO 2 -imid-PMA ( Esmaeilpour et al, 2015 ), NiFe 2 O 4 @SiO 2 –H 3 PW 12 O 40 ( Maleki et al, 2016 ), theophylline ( Mohamadpour, 2021c ), triethanolamine ( Rahnamaf et al, 2020 ), sodium alginate ( Mohamadpour, 2022a ), Fe 3 O 4 @SiO 2 @TiO 2 ( Khazaei et al, 2015 ), MgFe 2 O 4 nanoparticles ( Eshtehardian et al, 2020 ), trichloroisocyanuric acid ( Hojati et al, 2018 ), Na2 eosin Y ( Mohamadpour, 2021d ), DABCO ( Tahmassebi et al, 2011 ), and Pd nanoparticles ( Saha and Pal, 2012 ). There are limitations on metal catalysts such as, expensive reagents, severe reaction conditions, monotonous yields, environmental hazards, workup processes, and long reaction times associated with these methods.…”

Section: Introductionmentioning

confidence: 99%

Methylene Blue as a Photo-Redox Catalyst: The Development Synthesis of Tetrahydrobenzo[b]pyran Scaffolds via a Single-Electron Transfer/Energy Transfer

Mohamadpour

2022

Front. Chem.

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In a green tandem reaction using aldehyde derivatives, malononitrile, and dimedone, a radical tandem Knoevenagel–Michael cyclocondensation reaction of tetrahydrobenzo[b]pyran scaffolds was developed. Using visible light as a sustainable energy source, methylene blue (MB+)-derived photo-excited state functions were employed in an aqueous solution as single-electron transfer (SET) and energy transfer catalysts. The range of yields is quite uniform (81–98%, average 92.18%), and the range of reaction time is very fast (2–7 min, average 3.7 min), and the point mentioned in the discussion is that the procedure tolerates a range of donating and withdrawing groups, while still giving very excellent yields. The reaction is fairly insensitive to the nature of the substituents. Research conducted in this project aims to develop a non-metallic cationic dye that is both inexpensive and widely available for more widespread use. In addition to energy efficiency and environmental friendliness, methylene blue also offers an excellent atom economy, time-saving features, and ease of use. As a result, a wide range of long-term chemical and environmental properties can be obtained. The turnover number and turnover frequency of tetrahydrobenzo[b]pyran scaffolds have been computed. Surprisingly, gram-scale cyclization is a possibility, implying that the technology may be applied in industries.

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Section: Introductionmentioning

confidence: 99%

Methylene Blue as a Photo-Redox Catalyst: The Development Synthesis of Tetrahydrobenzo[b]pyran Scaffolds via a Single-Electron Transfer/Energy Transfer

Mohamadpour

2022

Front. Chem.

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“…Heterocyclic compounds are the cyclic organic compounds which contain at least one hetero atom, the most common heteroatoms are the nitrogen, oxygen and sulphur but heterocyclic rings containing other hetero atoms are also widely known. Carbocyclic compound a cyclic organic compound containing all carbon atoms in ring formation [1][2][3][4][5][6][7][8][9][10][11][12][13].The most common heterocycles are those having five-or six-membered rings and containing heteroatoms of nitrogen (N), oxygen (O), or sulfur (S). The best known of the simple heterocyclic compounds are pyridine, pyrrole, furan, and thiophene.…”

Section: Introductionmentioning

confidence: 99%

review on green multicomponent synthesis of heterocyclic compounds

D’souza

D’Souza

Mendonca

et al. 2022

ijhs

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Heterocyclic compounds are of very much concern in our daily life. These compounds constitute the largest and most varied family of organic compounds. Heterocyclic compounds have one or more hetero atoms in their structure., Day by day the number is increasing rapidly due to the enormous synthetic research and also their synthetic utility. They may be cyclic or non-cyclic in nature. They are predominantly used as pharmaceuticals, as agrochemicals and as veterinary products. They also find applications as sanitizers, developers, antioxidants, as corrosion inhibitors, as copolymers, dye stuff and anticancer drugs. They are used as vehicles in the synthesis of other organic compounds. In this review, we cover most biological active heterocyclic compounds that it’s recently synthesized or extracted from the plants e.g. antibiotics such as penicillin’s, cephalosporin; alkaloids such as vinblastine, morphine, reserpine etc. have heterocyclic moiety.

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“…Given this, a large number of catalysts were introduced for the three‐component synthesis of tetrahydrobenzo[ b ]pyran and pyrano[2,3‐ d ]‐pyrimidinone/thiones under multifarious catalytic circumstances. [ 9 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 ] There are numerous catalysts derived from fruit extracts, and agro‐wastes have been utilized to synthesize various heterocycles. [ 35 , 36 , 37 , 38 , 39 ]…”

Section: Introductionmentioning

confidence: 99%

WELPSA: A natural catalyst of alkali and alkaline earth metals for the facile synthesis of tetrahydrobenzo[b]pyrans and pyrano[2,3‐d]pyrimidinones as inhibitors of SARS‐CoV‐2

Nesaragi

Kamble

Hoolageri

et al. 2021

Applied Organom Chemis

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Since 2019, the infection of SARS‐CoV‐2 has been spreading worldwide and caused potentially lethal health problems. In view of this, the present study explores the most commodious and environmentally benign synthetic protocol for the synthesis of tetrahydrobenzo[ b ]pyran and pyrano[2,3‐ d ]pyrimidinones as SARS‐CoV‐2 inhibitors via three‐component cycloaddition of aromatic aldehyde, malononitrile, and dimedone/barbituric acid in water. Lemon peel from juice factory waste, namely, lemon ( Citrus limon ), sweet lemon ( C. limetta ), and Kaffir lime or Citron ( C. hystrix ), effectually utilized to obtain WELPSA, WESLPSA, and WEKLPSA, respectively, for the synthesis of title compounds. The catalyst was characterized by scanning electron microscope (SEM) and energy‐dispersive x‐ray spectroscopy (EDX). The concentration of sodium, potassium, calcium, and magnesium in the catalyst (WELPSA) was determined using atomic absorption spectrometry (AAS). The current approach manifests numerous notable advantages that include ease of preparation, handling and benignity of the catalyst, low cost, green reaction conditions, facile workup, excellent yields (93%–97%) with extreme purity, and recyclability of the catalyst. Compounds were docked on the crystal structure of SARS‐CoV‐2 (PDB: 6M3M). The consensus score obtained in the range 2.47–4.63 suggests that docking study was optimistic indicating the summary of all forces of interaction between ligands and the protein.

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Mild and green synthesis of tetrahydrobenzopyran, pyranopyrimidinone and polyhydroquinoline derivatives and DFT study on product structures

Cited by 69 publications

References 29 publications

Methylene Blue as a Photo-Redox Catalyst: The Development Synthesis of Tetrahydrobenzo[b]pyran Scaffolds via a Single-Electron Transfer/Energy Transfer

Methylene Blue as a Photo-Redox Catalyst: The Development Synthesis of Tetrahydrobenzo[b]pyran Scaffolds via a Single-Electron Transfer/Energy Transfer

review on green multicomponent synthesis of heterocyclic compounds

WELPSA: A natural catalyst of alkali and alkaline earth metals for the facile synthesis of tetrahydrobenzo[b]pyrans and pyrano[2,3‐d]pyrimidinones as inhibitors of SARS‐CoV‐2

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