Synthesis of Annelated 1,2,3-Selena- or -Thia-diazoles

Reddy, D. Bhaskar; Reddy, A. Somasekhar; Padmavathi, V.

doi:10.1039/a804381g

Cited by 25 publications

(8 citation statements)

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“…Michael addition reaction of appropriate carboanionic reagents to α,β-unsaturated carbonyl compounds such as chalcones is of synthetic interest for C-C bond formation [10]. Addition of 1,3-dicarbonyl compounds such as malonate esters and acetoacetate esters is important for synthesis of 1,5-dicarbonyl compounds which are the key compounds for the preparation of many biological heterocyclic compounds [11]. Many studies have been reported on related addition of diethyl malonate to chalcone derivatives [12][13].…”

Section: Introductionmentioning

confidence: 99%

<b>Preparation of diethyl malonate adducts from chalcone analogs containing a thienyl ring</b>

Budak¹,

Gürdere²,

Keçeci³

et al. 2010

Bull. Chem. Soc. Eth.

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Section: Introductionmentioning

confidence: 99%

<b>Preparation of diethyl malonate adducts from chalcone analogs containing a thienyl ring</b>

Budak¹,

Gürdere²,

Keçeci³

et al. 2010

Bull. Chem. Soc. Eth.

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“…Cyclohexenones are cyclic chalcones derive from the Michael additions of ethyl acetoacetate to chalcones, followed by internal aldol condensation . Literature revealed that the cyclic chalcones possess numerous pharmacological properties including anti‐cancer, anti‐HIV, anti‐fungal, anti‐tumor, anticonvulsant, and antitubercular activity .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, spectroscopic characterization, and computed optical analysis of green fluorescent cyclohexenone derivatives

Nazar

Badshah

Mahmood

et al. 2015

J. Phys. Org. Chem.

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Cyclohexenone containing chalcones core is one important class of materials, which exhibit high nonlinear optical (NLO) responses and good crystallizability. The present study reports the successful development of six new fluorescent cyclohexenone derivatives (CDs) via conventional Robinson annulation method. The molecular structures of these newly synthesized CDs were confirmed by using various analytical techniques such as 1 H NMR, 13 C NMR, FTIR, EIMS, UV-Vis spectroscopy and single crystal X-ray diffraction. The crystallographic data revealed that the spatial structure of the representative CD (4BE) belongs to monoclinic, P2 1 /c space group. The results from luminescence studies show that the CDs molecules apparently emit intense green light at room temperature in aqueous media. The relative polarity and molecular chemical stability of the CDs molecules were predicted by measuring the molecular electrostatic potential and frontier molecular orbital energy. In addition, the UV-Vis spectra, transition character and electronic structures of these CDs were computed by using quantum chemical methodology. It was interesting to note that the values of computed and experimental electronic transitions (λ max ) were in good agreement and these CDs display high hyperpolarizability (β) values. The present work will be helpful for systematical understanding of the structures and the optical properties of CDs for studying the structure-activity relationship that will suggest their potential application in photonic devices.Yellow solid, Yield 3.5 g (65.0%); m.p.: 126-127°C. 1 H NMR (CDCl 3 , 300 MHz): δ 1.07 (t, J = 7.2 Hz, 3H), 4.08 (q, J = 7.2 Hz, 2H), 3.03 (dd, J 1 = 2.2 Hz, J 2 = 18.0, 1H), 2.71-2.81 (m, 1H), 3.73 (dd J 1 = 2.9 Hz, J 2 = 6.9, 2H), 6.53 (s, 1H), 7.44 (dd J 1 = 2.8 Hz, J 2 = 6.85, 2H), 7.02 (dd J 1 = 2.5 Hz, J 2 = 6.9, 2H), 6.85 (dd J 1 = 2.1 Hz, J 2 = 6.6, 2H), 7.23 (dd J 1 = 3.0 Hz, J 2 = 6.6, 2H), 1.43 (t, J = 7.2 Hz, 3H), 4.09 (q, J = 7.1 Hz, 2H). 13 C NMR (CDCl 3 , 300 MHz): δ 193.6, 169.3, 160.3, Scheme 1. General methodology for the synthesis of cyclohexenone derivatives

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“…It is known that a weak base or acid such as piperidine [7] or phosphorus trichloride [8] often afforded open chain adducts, while cyclic products have been obtained in presence of sodium methoxide [2] or sodium hydroxide [9]. Particularly, the products of these cyclic reactions are of interest in term of their stereochemistry and as starting materials for the synthesis of compounds with possible biological activity [10,11]. Reddy et al have reported that the synthesis of 1,1-disubstituted-2,6-diarylcyclohexane-4-ones was carried out in moderate to good yields via double Michael addition of bis-chalcone with active methylene compounds in the presence of sodium methoxide at reflux temperature in alcohol [12], but the catalyst cannot be recycled.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 1,1-disubstituted-2,6-diarylcyclohexane-4-ones catalyzed by KF/basic Al2O3 under ultrasound

Li¹,

Xu²,

Chen³

et al. 2005

Ultrasonics Sonochemistry

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Synthesis of Annelated 1,2,3-Selena- or -Thia-diazoles

Cited by 25 publications

References 5 publications

<b>Preparation of diethyl malonate adducts from chalcone analogs containing a thienyl ring</b>

<b>Preparation of diethyl malonate adducts from chalcone analogs containing a thienyl ring</b>

Synthesis, spectroscopic characterization, and computed optical analysis of green fluorescent cyclohexenone derivatives

Synthesis of 1,1-disubstituted-2,6-diarylcyclohexane-4-ones catalyzed by KF/basic Al2O3 under ultrasound

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