Synthesis of 2-amino-7-hydroxy-4H-chromene derivatives under ultrasound irradiation: A rapid procedure without catalyst

Safari, Javad; Heydarian, Marzieh; Zarnegar, Zohre

doi:10.1016/j.arabjc.2013.11.038

Cited by 29 publications

(18 citation statements)

References 24 publications

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“…The pathway for the preparation of the target compounds is outlined under (1) is the key compound in our study for the production of its functionalized derivatives [52]. Compound 1 was condensed with cyanothioacetamideunder basic condition to give11-amino-12-(4-methoxyphenyl)-9-thioxo-9,12dihydro-8H-benzo [5,6] chromeno[2,3-b]pyridin-10-carbonitrile (2) (Scheme 1). The NMR spectra revealed two D2O replaceable main peaks at 6.9 and 8.3 ppm related to the presence of NH2 and NH protons.…”

Section: Chemistrymentioning

confidence: 99%

“…The NMR spectra revealed two D2O replaceable main peaks at 6.9 and 8.3 ppm related to the presence of NH2 and NH protons. Additionally, compound 1 was allowed to react with phenyl isothiocyanatein order to form 11-imino-12-(4-methoxyphenyl)-10phenyl,10,11-dihydro-8H-benzo [5,6]chromeno[2,3-d] pyrimidin-9-(12H) thione (3). The NMR spectra of compound 3 showed two D2O changeable singles at 8.3 and 8.4 ppm corresponding to NH and =NH, respectively.…”

Section: Chemistrymentioning

confidence: 99%

“…The NMR spectra of compound 3 showed two D2O changeable singles at 8.3 and 8.4 ppm corresponding to NH and =NH, respectively. Basic catalyzed reaction of 1 with malononitrile afforded 9,11-diamino-12-(4-methoxyphenyl)-14,12H-benzo [5,6] chromeno[2,3-b]pyridin-10-carbonitrile (4). Interaction of compound 1 with carbon disulfide in dimethyl sulfoxide gave 9mercapto [2,3-d]pyrimidin-11-thione derivative (5) (Scheme 1).…”

Section: Chemistrymentioning

confidence: 99%

“…Imidazo [1,2-c]pyrimidin-5-amine derivative (11) was obtained via intermolecular cyclization of the compound 6 with phenyl isothiocyanate. Compound 6 was heated with chloroacetyl chloride in glacial acetic acid at 60 °C to provide 5-(chloromethyl)-14-(4-methoxyphenyl)-3,14-dihydro-2H-benzo [5,6] chromeno[3,2-e]imidazo[1,2-c]pyrimidine (12) (Scheme 3). IR data of compound 12 indicated a peak at υ 744.5 cm -1 for C-Cl and disappearance of NH2 and NH groups that could be related to their involvement in the cyclization process.…”

Section: Scheme 2: Synthesis Of Benzo[56]-chromeno[32-e]imidazo[12mentioning

confidence: 99%

“…The mass spectrum of compound 12 showed a molecular ion peak at m/z 472 (M + , 2%), 406 (M + +2, 8%), which indicate the presence of Cl atom. The cyclo condensation of compound 6 with 1,4-dichlorobutane in DMF in the presence of anhydrous potassium carbonate led to the formation of imidazo[1,2-a] [1,5]diazocine derivative (13).…”

Section: Scheme 2: Synthesis Of Benzo[56]-chromeno[32-e]imidazo[12mentioning

confidence: 99%

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Synthesis and Utility of New Polycyclic Compounds as Potential Antimicrobials Based on Chromene Moiety

Abdelaziz

Zarie

Sarhan

2019

Int J Pharm Pharm Sci

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Objective: The present research aims to synthesize some new polycyclic compounds including chromene moiety and study their antimicrobial activity.Methods: Several new polycyclic systems including chromene scaffold incorporated with pyridine, pyrimidine, imidazopyrimidine, and imidazodiazocine were achieved via condensation reaction of chromene derivative under the proper condition with various reagents namely; cyanothioacetamide, phenyl isothiocyanate, malononitrile, carbon disulfide, benzaldehyde, triethylorthoformate, and 1,4-dichlorobutane. Moreover, a chlorodiazenyl chromene derivative was reacted with some substances possessing active-CH2-bridge such as ethyl cyanoacetate and malononitrile to end up with hydrazono compounds. Such compounds were eventually cyclized with hydrazine hydrate to form pyrazole and oxopyrazole derivatives. Moreover, compound 1 was treated with benzoyl acetone, and then followed by cyclization with malononitrile to provide the corresponding 2-amino14-(4-methoxyphenyl)-4-methy-5-phenyl-14H-benzo[5,6] chromeno [2,3H][1,6]naphthyridine-3-carbonitrile (20). Results:The results of the antimicrobial screening in vitro revealed that the inhibition zone (mm) of the synthesized compounds 1-3, 5 and 8 implied their optimum antibacterial activity, while the compounds 4, 6 and 9-13, 15 showed a moderate to weak antibacterial activity against multiple species of B. subtilis, S. aureus, E. coli and P. aeruginosa. In contrast, the compounds 1, 6, 11, 15 showed high antifungal activities against different species of A. flavinand C. albicans, while the other compounds exhibit a moderate to poor antifungal activity. Conclusion:It is remarkable that a series of chromene derivatives synthesized by a simple and available method leads to a molecule of promising antimicrobial activity. Further research is recommended to approve the importance of polycyclic systems for various applications.

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Section: Chemistrymentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

Section: Scheme 2: Synthesis Of Benzo[56]-chromeno[32-e]imidazo[12mentioning

confidence: 99%

Section: Scheme 2: Synthesis Of Benzo[56]-chromeno[32-e]imidazo[12mentioning

confidence: 99%

See 3 more Smart Citations

Synthesis and Utility of New Polycyclic Compounds as Potential Antimicrobials Based on Chromene Moiety

Abdelaziz

Zarie

Sarhan

2019

Int J Pharm Pharm Sci

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An inorganic–organic hybrid material based on a Keggin‐type polyoxometalate@Dysprosium as an effective and green catalyst in the synthesis of 2‐amino‐4H‐chromenes via multicomponent reactions

Hosseinzadeh‐Baghan

Mirzaei

Eshtiagh‐Hosseini

et al. 2020

Applied Organom Chemis

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New insight into experimental and theoretical mechanistic study on a green synthesis of functionalized 4H‐chromenes using magnetic nanoparticle catalyst

Ghavidel

Mirza

Soleimani‐Amiri

et al. 2020

J Chinese Chemical Soc

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A green synthesis of functionalized 4H-chromenes using one-pot, threecomponent reaction of salicylaldehyde (1), active methylene (2), and carbonbased nucleophile (3) using Fe 3 O 4 @CONa nanoparticles in water has been performed at 60 C. The Fe 3 O 4 @CONa nanoparticle as an efficient, green, and magnetically reusable heterogeneous catalyst was applied in these reactions up to the nine runs. Green catalyst and solvent, short reaction time, high product yields, as well as simple work-up procedure were found as some advantages of this methodology. The density functional theory calculations were applied to all-inclusive perception of the one-pot, three-component reaction mechanism. The most reactions progressed through the following route: (a) nucleophilic addition of 2 to 1; (b) ring closing, dehydration; (c) nucleophilic substitution of 3 (2-naphtol, 4-hydroxycumarin) to intermediate. Sometimes mechanism mutated to: (a) nucleophilic addition of 3 (indole, 2-methylindole) to 1, and dehydration; (b) nucleophilic addition of 2 to intermediate; and (c) ring closing, and dehydration. The frontier molecular orbitals, NBO analyses, molecular electrostatic potential of reactants, and intermediates confirmed the proposal mechanisms. Theoretical study could be so helpful to pick out suitable reactants of the reaction.

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Synthesis of 2-amino-7-hydroxy-4H-chromene derivatives under ultrasound irradiation: A rapid procedure without catalyst

Cited by 29 publications

References 24 publications

Synthesis and Utility of New Polycyclic Compounds as Potential Antimicrobials Based on Chromene Moiety

Synthesis and Utility of New Polycyclic Compounds as Potential Antimicrobials Based on Chromene Moiety

An inorganic–organic hybrid material based on a Keggin‐type polyoxometalate@Dysprosium as an effective and green catalyst in the synthesis of 2‐amino‐4H‐chromenes via multicomponent reactions

New insight into experimental and theoretical mechanistic study on a green synthesis of functionalized 4H‐chromenes using magnetic nanoparticle catalyst

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