- Knoevenagel-Cyclization Cascade Reactions of Substituted 5,6-Dihydro-2H-Pyran Derivatives
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The diastereoselective domino-Knoevenagel-IMHDA reactions of 5,6-dihydro-2H-pyran derivatives containing an o-formylaryl amine or ether moiety were performed with active methylene reagents. In the spiro heterocyclic products representing a novel skeleton, a tetrahydroquinoline or chroman unit is fused with two pyran rings and the bridgehead carbon atoms are chirality centers formed diastereoselectively. Depending on the substitution pattern, a domino Knoevenagel-[1,5]-hydride shift-cyclization sequence was identified as a competing pathway, which resulted in the formation of tetrahydroquinoline derivatives with a 5,6-dihydro-2H-pyran-3-yl substituent. The relative configurations of the products were determined by means of the characteristic NOE correlations and single crystal X-ray diffraction analysis. Antiproliferative activity assays of two products against A2780 and WM35 human cancer cell lines showed low micromolar IC50 values down to 2.99 μM.
- Bényei, Attila,Bíró, Tamás,Király, Sándor Balázs,Kurtán, Tibor,Lisztes, Erika,Tóth, Balázs István
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supporting information
p. 6161 - 6170
(2021/12/10)
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- METHOD FOR PRODUCING CONDENSED HETEROCYCLIC COMPOUND
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PROBLEM TO BE SOLVED: To provide a novel and industrially advantageous method for producing a condensed heterocyclic compound useful as an agrochemical. SOLUTION: A high-yield and inexpensive method for producing a compound represented by formula (1) comprises synthesis of a pyridine derivative having a cyclopropyl group at the 5-position, and a subsequent reaction. (In the formula, n and m are integers from 0 to 2.) SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT
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Paragraph 0090
(2020/11/12)
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- Carbon Dioxide Copolymerization Study with a Sterically Encumbering Naphthalene-Derived Oxide
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Poly(1,4-dihydronaphthalene carbonate) has been prepared via the catalytic coupling of carbon dioxide and 1,4-dihydronaphthalene oxide using chromium(III) catalysts. The copolymer formation is found to be greatly dependent on the steric environment around the metal center. Traditional (salen)CrIIIX/cocatalyst systems bearing bulky t-butyl groups hinder the approach of the large monomer, significantly diminishing polymer chain growth and providing the entropically favored cyclic byproduct in excess. In contrast, employing the sterically unencumbered azaannulene-derived catalyst, (tmtaa)CrIIIX/cocatalyst system (tmtaa = tetramethyltetraazaannulene) shows polymer selectivity close to 90% with three times the activity (TOF = 20-30 h-1). With the use of a bifunctional (salen)CrIII catalyst, even higher polymer selectivity (>90%) can be observed. The complete synthesis of a new bifunctional tetraazaannulene ligand for a more effective catalyst is also described herein.
- Darensbourg, Donald J.,Kyran, Samuel J.
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p. 5421 - 5430
(2015/09/15)
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- Synthesis and evaluation of pyrazolo[3,4-b]pyridines and its structural analogues as TNF-α and IL-6 inhibitors
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In the present article, we have synthesized three different series of pyrazolo[3,4-b]pyridines and their structural analogues using novel synthetic strategy involving one-pot condensation of 5,6-dihydro-4H-pyran-3-carbaldehyde/2-formyl-3,4,6-tri-O-methyl-d-glucal /chromone-3-carbaldehyde with heteroaromatic amines. All synthesized compounds were evaluated for their anti-inflammatory activity against TNF-α and IL-6. Out of 28 compounds screened, 40, 51, 52 and 56 exhibited promising activity against IL-6 with 60-65% inhibition at 10 μM concentration. Amongst these, 51, 52 and 56 showed potent IL-6 inhibitory activity with IC50's of 0.2, 0.3 and 0.16 μM, respectively. Compound 56 was not cytotoxic in CCK-8 cells up to the concentration of >100 μM.
- Bharate, Sandip B.,Mahajan, Tushar R.,Gole, Yogesh R.,Nambiar, Mahesh,Matan,Kulkarni-Almeida, Asha,Balachandran, Sarala,Junjappa,Balakrishnan, Arun,Vishwakarma, Ram A.
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p. 7167 - 7176
(2008/12/22)
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- Direct formylation of enol ethers using cyanuric chloride and N,N-dimethylformamide
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A new method to prepare α,β-unsaturated enol aldehydes is described. 3-Ethoxymethacrolein (1) and 5-formyl-3,4-dihydro-2H-pyran (5) were effectively prepared from enol ethers and the Vilsmeier-Haack type complex, derived from cyanuric chloride and DMF. One byproduct, amidine 4, was also characterized.
- Hou, Duen-Ren,Sun, Chong-Si,Sie, Wu-Sian,Jian, Jing-Yu,Hsu, Yun
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p. 671 - 674
(2007/10/03)
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- 1,8-Dihydro-6,13-bis(3-hydroxypropyl)-1,4,8,11-tetraazaannulenes from 3,4-Dihydro-2H-pyran-5-carbaldehyde
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1,8-Dihydro-6,13-bis(3-hydroxypropyl)-1,4,8,11-tetraazaannulenes 6 are synthesized from 1,2-benzenediamines 5 and 3,4-dihydro-2H-pyran-5-carbaldehyde (3a) as a cyclic 3-alkoxyacrolein.These macrocyclic N4 ligands chelate nickel(II) ions.The nickel(II) chelates 7 are also directly obtained by metal template condensation of the 1,2-diamines 5, the aldehyde 3a and nickel(II) acetate.
- Hanke, Reiner,Breitmaier, Eberhard
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p. 1657 - 1661
(2007/10/02)
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