Furopyridines. Synthesis and Properties

Shiotani, Shunsaku

doi:10.3987/rev-97-488

Cited by 38 publications

(21 citation statements)

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“…Shiotani's group was one of the first team interested in furopyridine scaffolds. In 1997, they summarized their results in an interesting review dealing with the synthesis and the reactivity of furopyridines 4…”

Section: Introductionmentioning

confidence: 99%

Phosphate Monoester Hydrolysis by Trinuclear Alkaline Phosphatase; DFT Study of Transition States and Reaction Mechanism

Chen

Liao

2014

ChemPhysChem

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Alkaline phosphatase (AP) is a trinuclear metalloenzyme that catalyzes the hydrolysis of a broad range of phosphate monoesters to form inorganic phosphate and alcohol (or phenol). In this paper, by using density functional theory with a model based on a crystal structure, the AP-catalyzed hydrolysis of phosphate monoesters is investigated by calculating two substrates, that is, methyl and p-nitrophenyl phosphates, which represent alkyl and aryl phosphates, respectively. The calculations confirm that the AP reaction employs a "ping-pong" mechanism involving two chemical displacement steps, that is, the displacement of the substrate leaving group by a Ser102 alkoxide and the hydrolysis of the phosphoseryl intermediate by a Zn2-bound hydroxide. Both displacement steps proceed via a concerted associative pathway no matter which substrate is used. Other mechanistic aspects are also studied. Comparison of our calculations with linear free energy relationships experiments shows good agreement.

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Section: Introductionmentioning

confidence: 99%

Phosphate Monoester Hydrolysis by Trinuclear Alkaline Phosphatase; DFT Study of Transition States and Reaction Mechanism

Chen

Liao

2014

ChemPhysChem

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“…The following compounds were prepared with above described general procedure. 6, 118.2, 122.1, 127.5, 128.8, 129.3, 130.8, 137.0, 145.7, 148.1, 154 2,20.1,31.7,34.8,97.1,118.4,122.0,142.7,144.6,147.1,155.7;MS (EI) NO: C,75.43;H,7.43;N,8.00;found: C,75.61;H,7.53;N,7.95.…”

Section: Methodsmentioning

confidence: 99%

“…The product was obtained as a colorless oil (62%) from 2bromo-3-hydroxypyridine and 4-pentyn-1-ol after 20 h of reaction; 1 H NMR (400 MHz, CDCl 3 ) δ 2.26 (m, 2H), 2.73 (t, J = 7.4 Hz, 2H), 3.56 (t,J = 7.4 Hz,2H),6.75 (s,1H),7.26 (dd,J = 5.2,2.0 Hz,1H),7.75 (d,J = 8.0 Hz,1H),8.43 (d,J = 4.8 Hz,1H); 13 C NMR (100 MHz, CDCl 3 ) δ 30. 1, 31.7, 60.3, 97.1, 118.0, 122.1, 142.6, 144.5, 147.3, 155. (22); calcd for C 10 H 11 NO 2 : C,67.80;H,6.21;N,7.91;found: C,67.87;H,6.23;N,7. 5,29.5,34.2,62.1,97.1,118.8,122.0,142.7,144.0,146.6,155.2;MS (EI) (22); calcd for C 11 H 13 NO 2 : C, 69.11; H, 6.81; N, 7.33; found: C, 69.01; H, 6.83; N, 7. 5, 121.5, 125.2, 128.9, 129.3, 129.5, 129.6, 143.9, 155.7, 161.9; MS (EI) m/z 196 (M + , 100), 197 (M + 1, 12); calcd for C 13 H 9 NO: C, 80.00; H, 4.61; N, 7.18; found: C, 80.18; H, 4.58; N, 7.12.…”

Section: -(3-hydroxypropyl)furo[32-b]pyridine (2d)mentioning

confidence: 99%

“…The product was obtained as a colorless oil (70%) from 3-bromo-2hydroxypyridine and 1-hexyne after 18 h of reaction; 1 8, 22.2, 28.3, 29.4, 100.9, 118.9, 121.1, 128.7, 142.7, 159.8, 161.9; MS (EI) m/z 175 (M + , 100), 190 (40), 124 (10); calcd for C 11 H 13 NO: C,75.43;H,7.43;N,8.00;found: C,75.52;H,7.38;N,7. 3, 61.8, 101.4, 119.1, 121.0, 128.9, 142.9, 158.9; MS (EI) m/z 177 (M + , 50), 159 (85), 132 (100), 83 (45); calcd for C 10 H 11 NO 2 : C,67.80;H,6.21;N,7.91;found: C,67.75;H,6.18;N,7.93. Table 6.…”

Section: -Butylfuro[23-b]pyridine (3b)mentioning

confidence: 99%

“…The product was obtained as a pale yellow oil (48%) from 3-bromo-2hydroxypyridine and 5-hexyn-1-ol after 22 h of reaction; 1 H NMR (400 MHz, CDCl 3 ) δ 1.69 (m, 2H), 1.90 (m, 2H), 2.85 (t, J = 7.2 Hz, 2H), 3.71 (t, J = 6.4 Hz, 2H), 6.41 (s,1H),7.17 (dd,J = 7.6,4.8 Hz,1H),7.81 (d,J = 7.6 Hz,1H),8.22 (d,J = 4.8 Hz,1H); 13 C NMR (100 MHz, CDCl 3 ) δ 23. 6,28.3,32.0,62.4,101.2,119.0,121.0,128.8,142.7,159.2,161.8;MS (EI) m/z 192 (M + ,100),131(5); calcd for C 11 H 13 NO 2 : C, 69.11; H, 6.81; N, 7.33; found: C, 69.25; H, 6.83; N, 7.25 4,115.9,127.5,128.8,129.1,130.2,142.2,148.8,154.0;MS (EI) m/ z 195 (M + ,100),116 (32); calcd for C 13 H 9 NO: C,80.00;H,4.61;N,7.18;found: C,80.13;H,4.58;N,7.23.…”

Section: -(Hydroxybutyl)furo[23-b]pyridine (3d)mentioning

confidence: 99%

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Copper‐ and Ligand‐free Heteroannulation of o‐Halohydroxypyridine with Terminal Alkynes Using Pd/C Catalyst: One‐Pot Synthesis of 2‐Substituted Furopyridines and their Functionalization

Park

Kim

Yum

et al. 2015

Bulletin Korean Chem Soc

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Three types of isomeric 2-substituted furo [3,2-b]pyridine, furo [2,3-b]pyridine and furo[3,2-c]pyridine were prepared using Pd/C-catalyzed heteroannulation of o-halopyridinols and terminal alkynes under copperand ligand-free conditions. We also demonstrated that double functionalization yielding 2,3-disubstituted furopyridines could be achieved through heteroannulation followed by bromination and Suzuki/Heck reactions. In addition, the use of recoverable Pd/C in the absence of a cocatalyst and ligand can aid in the development of greener chemical processes.

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Conjugated Dienyne‐Imides as Robust Precursors of 1‐Azatrienes for 6π Electrocyclizations to Furo[2,3‐b]dihydropyridine Cores

Wan

Zheng

2018

Angewandte Chemie

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A novel strategy to generate functionalized 1‐azatriene intermediates for 6π electrocyclizations was developed by using readily accessible dienyne‐imides and various terminal olefins under PdII catalysis. Taking advantage of the sequential cooperation between preloaded and incorporated functional handles at 1,3‐dien‐5‐yne skeletons, this method not only enables the selective generation of putative 1‐azatrienes but significantly accelerates their thermal 6π‐electrocyclic ring‐closure processes to a series of highly substituted furo[2,3‐b]dihydropyridine derivatives in good yields.

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Furopyridines. Synthesis and Properties

Cited by 38 publications

References 0 publications

Phosphate Monoester Hydrolysis by Trinuclear Alkaline Phosphatase; DFT Study of Transition States and Reaction Mechanism

Phosphate Monoester Hydrolysis by Trinuclear Alkaline Phosphatase; DFT Study of Transition States and Reaction Mechanism

Copper‐ and Ligand‐free Heteroannulation of o‐Halohydroxypyridine with Terminal Alkynes Using Pd/C Catalyst: One‐Pot Synthesis of 2‐Substituted Furopyridines and their Functionalization

Conjugated Dienyne‐Imides as Robust Precursors of 1‐Azatrienes for 6π Electrocyclizations to Furo[2,3‐b]dihydropyridine Cores

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