Concise synthesis of chiral 2(5H)-furanone derivatives possessing 1,2,3-triazole moiety via one-pot approach

Tan, Yue‐He; Li, Jianxiao; Xue, Fuling; Qi, Ji; Wang, Zhaoyang

doi:10.1016/j.tet.2012.01.092

Cited by 26 publications

(18 citation statements)

References 107 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The serial multi‐chiral diacetylene (DA) monomers 1 possessing 2(5 H )‐furanone structure were synthesized via the Glaser reaction of N ‐[5‐( S )‐alkoxy‐2(5 H )‐furanonyl] amino acid propargyl esters 6 (Scheme S1, Supporting Information), and systematically characterized by 1 H NMR, 13 C NMR, FTIR, UV, MS, and elemental analysis (see their data, especially their spectra and the discussion on the structural characterization of DA monomers 1 in the Supporting Information). DA monomers 1 are constructed from four parts, 2(5 H )‐furanone, L ‐menthol, amino acid, and propargyl bromide, and the former three units may make 1 have multiple chiral centers (Scheme S1, Supporting Information), which can easily bring the novel chiral PDAs with tunable structure.…”

Section: Resultsmentioning

confidence: 99%

Electrophoretic Deposition Polymerization of Diacetylenes with Tunable Structure

Huo

Deng

et al. 2013

Macromol. Rapid Commun.

View full text Add to dashboard Cite

Serial novel chiral polydiacetylenes (PDAs) are efficiently prepared at room temperature by the controllable electrophoretic deposition of diacetylenes with tunable structure as designed from easily available starting materials. The colorimetrically reversible properties of PDAs in the range between 25 and 85 °C are influenced by the different amino acid moiety in the PDAs as anticipated. The PDA containing aromatic ring is much better for the colorimetrically reversible properties, while irreversible thermochromism is displayed for the PDA with the structure of the longer methylene units in the main chain of amino acid moiety.

show abstract

Section: Resultsmentioning

confidence: 99%

Electrophoretic Deposition Polymerization of Diacetylenes with Tunable Structure

Huo

Deng

et al. 2013

Macromol. Rapid Commun.

View full text Add to dashboard Cite

show abstract

“…The alkyl azide intermediate was prepared according to the reported procedures. 31 Melting points were uncorrected. IR spectra were recorded with an FTIR spectrometer.…”

Section: Methodsmentioning

confidence: 99%

Design, Synthesis, and Characterization of 1,3,5-Tri(1H-benzo[d]imidazol-2-yl)benzene-Based Fluorescent Supramolecular Columnar Liquid Crystals with a Broad Mesomorphic Range

et al. 2014

Self Cite

View full text Add to dashboard Cite

A new kind of supramolecular columnar liquid crystal T-A with a broad mesomorphic range (up to 164.9 °C), good thermal stability, and strong fluorescence is designed and formed by the H-bonding between 1,3,5-tri(1H-benzo[d]imidazol-2-yl)benzene (T) and serial gallic acid derivatives (A). Two components are easily available because of simple routes, common reactions, high yields, commercial starting materials, and inexpensive catalysts. The introduction of the 1,2,3-triazole structure into component A makes the textures different and is slightly disadvantageous for the T-A complexes.

show abstract

“…尽管该方法具有产率高、只生成水作为副产物等优点, 但所使用的金属催化剂三氟甲磺酸铋因易吸潮、价格昂贵等不足使其不便于推广应用. 本文在前期各种关于 2(5H)-呋喃酮化学研究中 [7,16,17] 尽管如此, 这些 5-(4'-烷氧基-4-联苯氧基)-3,4-二卤-2(5H)-呋喃酮化合物的产率较低, 特别是与以往粘卤酸与薄荷醇、冰片、甲醇、乙醇、苯甲醇等醇类化合物 70% 以上的醚化产率 [7,16,17] 各种共振结构中, 由于 1-位氧原子上的孤对电子可存在较大程度的共轭作用, 相比之下 Ia 是最稳定的, 因此导致了目标化合物 6 的生成(Scheme 2). 同时, 由于粘氯酸 5a 比粘溴酸 5b 多存在一种共振结构, 故以 5a…”

Section: (5h)-呋喃酮结构单元广泛存在于天然产物中unclassified

“…总之, 相对于醇类化合物与粘卤酸进行醚化反应产率高的事实 [7,16,17] , 对本实验中酸催化的 4'-烷氧基-4-联苯酚 (Scheme 2), 但有待在未来的研究中寻找更多的证据. [2,17,18] , 有利于其进一步转化为其他的 2(5H)- 9, 19.3, 31.4, 67.8, 99.3, 114.9, 118.0, 124.9, 128.0, 128.1, 132.4, 137.7, 147.0, 154.7, 158.8, 162.8;IR (film) ν: 3051, 2967IR (film) ν: 3051, , 2930IR (film) ν: 3051, , 2872IR (film) ν: 3051, , 1796IR (film) ν: 3051, , 1640IR (film) ν: 3051, , 1606IR (film) ν: 3051, , 1501IR (film) ν: 3051, , 1474IR (film) ν: 3051, , 1240IR (film) ν: 3051, , 1098IR (film) ν: 3051, , 1022 C NMR (CDCl 3 , 100 MHz) δ: 13.…”

Section: (5h)-呋喃酮结构单元广泛存在于天然产物中unclassified

Synthesis of 2(5H)-Furanone Derivatives with Biphenyl Ether Unit

关丽涛¹,

莫广珍²,

吴彦城³

et al. 2015

Chin. J. Org. Chem.

View full text Add to dashboard Cite

Sixteen 5-(4'-alkoxybiphenyl-4-yloxy)-3,4-dihalo-2(5H)-furanones are synthesized via the direct dehydrative etherification reactions of 4'-alkoxybiphenyl-4-ol with mucochloric acid and mucobromic acid, respectively, using sulfuric acid as catalyst at reflux in toluene from 30% to 58% yields (mostly over 47%). The moderate yields may be due to that this acid-catalyzed etherification should be a S N 2 nucleophilic substitution reaction. The structures of all newly synthesized compounds are elucidated and confirmed by FTIR, UV, 1 H NMR, 13 C NMR, and elemental analysis. The synthetic procedures afford not only an important strategy for the synthesis of 2(5H)-furanone derivatives having potential bioactivity, but also a simple method for the synthesis of aromatic ether from two different hydroxyl compounds.

show abstract

Concise synthesis of chiral 2(5H)-furanone derivatives possessing 1,2,3-triazole moiety via one-pot approach

Cited by 26 publications

References 107 publications

Electrophoretic Deposition Polymerization of Diacetylenes with Tunable Structure

Electrophoretic Deposition Polymerization of Diacetylenes with Tunable Structure

Design, Synthesis, and Characterization of 1,3,5-Tri(1H-benzo[d]imidazol-2-yl)benzene-Based Fluorescent Supramolecular Columnar Liquid Crystals with a Broad Mesomorphic Range

Synthesis of 2(5H)-Furanone Derivatives with Biphenyl Ether Unit

Contact Info

Product

Resources

About