An efficient and practical chemo-enzymatic route to (3R,3aR,6R,6aR)-hexahydrofuro[3,2-b]furan-6-amino-3-ol (6-aminoisomannide) from renewable sources

SynOpen ◽

10.1055/a-1532-5825 ◽

2021 ◽

Author(s):

Valerio Zullo ◽

Antonella Petri ◽

Anna Iuliano

Keyword(s):

Hydroxy Group ◽

Sodium Azide ◽

Hydroxyl Group ◽

Azido Group ◽

One Pot ◽

Renewable Sources ◽

Nucleophilic Displacement ◽

Trifluoromethanesulfonic Anhydride ◽

Enzymatic Route

The synthesis of 6-aminoisomannide is easily achieved starting from the renewable, inexpensive and commercially available isosorbide, in 66% overall yield. A biocatalysed highly regioselective acetylation of the 3-endo hydroxyl group of isosorbide was followed by the stereospecific interconversion of the 6-exo hydroxyl group into azido group, through reaction with trifluoromethanesulfonic anhydride followed by nucleophilic displacement of the triflate group by sodium azide. Finally, reduction of the azido group and deacetylation of the 3-hydroxy group were performed one pot by using LiAlH4.

Download Full-text

One-pot synthesis of 1-substituted 1H-1,2,3,4-tetrazoles from 2aminothiazoles using tributylmethylammonium chloride as a catalyst

Heterocyclic Communications ◽

10.1515/hc-2017-0039 ◽

2017 ◽

Vol 23 (5) ◽

Cited By ~ 3

Author(s):

Kerru Nagaraju ◽

Gummidi Lalitha ◽

Parvesh Singh ◽

Chunduri Venkata Rao

Keyword(s):

Sodium Azide ◽

Triethyl Orthoformate ◽

One Pot ◽

One Pot Synthesis ◽

Substituted 1

AbstractReaction between substituted thiazolylamine or oxazolylamine, triethyl orthoformate and sodium azide in the presence of tributylmethylammonium chloride in DMSO furnishes 1-substituted 1

Download Full-text

Synthesis of a Novel Series of Cu(I) Complexes Bearing Alkylated 1,3,5-Triaza-7-phosphaadamantane as Homogeneous and Carbon-Supported Catalysts for the Synthesis of 1- and 2-Substituted-1,2,3-triazoles

Nanomaterials ◽

10.3390/nano11102702 ◽

2021 ◽

Vol 11 (10) ◽

pp. 2702

Author(s):

Ivy L. Librando ◽

Abdallah G. Mahmoud ◽

Sónia A. C. Carabineiro ◽

M. Fátima C. Guedes da Silva ◽

Carlos F. G. C. Geraldes ◽

...

Keyword(s):

Aqueous Medium ◽

Sodium Azide ◽

Supported Catalysts ◽

Cycloaddition Reaction ◽

Water Soluble ◽

Terminal Alkynes ◽

One Pot ◽

Catalytic Systems ◽

Immobilized Catalyst ◽

High Yields

The N-alkylation of 1,3,5-triaza-7-phosphaadamantane (PTA) with ortho-, meta- and para-substituted nitrobenzyl bromide under mild conditions afforded three hydrophilic PTA ammonium salts, which were used to obtain a new set of seven water-soluble copper(I) complexes. The new compounds were fully characterized and their catalytic activity was investigated for the low power microwave assisted one-pot azide–alkyne cycloaddition reaction in homogeneous aqueous medium to obtain disubstituted 1,2,3-triazoles. The most active catalysts were immobilized on activated carbon (AC), multi-walled carbon nanotubes (CNT), as well as surface functionalized AC and CNT, with the most efficient support being the CNT treated with nitric acid and NaOH. In the presence of the immobilized catalyst, several 1,4-disubstituted-1,2,3-triazoles were obtained from the reaction of terminal alkynes, organic halides and sodium azide in moderate yields up to 80%. Furthermore, the catalyzed reaction of terminal alkynes, formaldehyde and sodium azide afforded 2-hydroxymethyl-2H-1,2,3-triazoles in high yields up to 99%. The immobilized catalyst can be recovered and recycled through simple workup steps and reused up to five consecutive cycles without a marked loss in activity. The described catalytic systems proceed with a broad substrate scope, under microwave irradiation in aqueous medium and according to “click rules”.

Download Full-text

Synthesis of 4-Nitrophenyl 2-Acetamido-2-deoxy-β-D-mannopyranoside and 4-Nitrophenyl 2-Acetamido-2-deoxy-α-D-mannopyranoside

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc20030801 ◽

2003 ◽

Vol 68 (4) ◽

pp. 801-811 ◽

Cited By ~ 14

Author(s):

Pavel Krist ◽

Marek Kuzma ◽

István F. Pelyvás ◽

Pavla Simerská ◽

Vladimír Křen

Keyword(s):

Sodium Azide ◽

Selective Reduction ◽

Epoxide Ring ◽

Azido Group

The title compounds were synthesized by the selective reduction of the azido group in 4-nitrophenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranoside (8) and 4-nitrophenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-mannopyranoside (11), and by subsequent acetylation. Compound 8 was prepared by opening of the epoxide ring in methyl 2,3-anhydro-4,6-O-benzylidene-α-D-glucopyranoside (1) with sodium azide, followed by inversion of the configuration at C-3 in the resulting altropyranoside and glycosidation with 4-nitrophenol.

Download Full-text

Funktionalisierte tripod-Liganden mit Neopentan-Grundgerüst: Umsetzung von HOCH2C(CH2PR2)3 mit Elektrophilen / Functionalized tripod-Ligands with N eopentane Fram ew ork: R eaction of HOCH2C(CH2PR2)3 with Electrophiles

Zeitschrift für Naturforschung B ◽

10.1515/znb-1995-0902 ◽

1995 ◽

Vol 50 (9) ◽

pp. 1287-1306 ◽

Cited By ~ 12

Author(s):

Thomas Seitz ◽

Alexander Asam ◽

Gottfried Hüttner ◽

Olaf Walter ◽

Laszlo Zsolnai

Keyword(s):

Hydroxy Group ◽

Analytical Techniques ◽

One Pot ◽

X Ray ◽

One Pot Synthesis ◽

Tripod Ligands ◽

Esterification Reactions ◽

New Compounds

AbstractSeveral ways to functionalize hydroxy-tripod-ligands (HOCH2C(CH2PR2)3) by activation with electrophiles are presented. The use of carboxylic halides and anhydrides is shown to be generally successful for esterification reactions in a one-pot synthesis starting from the oxetanes O(CH2)2C(CH2PR2)2. Facial coordinaton of the related esters towards iron(II) and molybdenum(O) can be achieved depending on the nature of the phosphane donor groups. If methyliodide or trimethylsilylchloride are used as electrophiles in order to functionalize the hydroxy group in HOCH2C(CH2PR2)3, it is necessary to proctect the phosphane groups by formation of the tris-borane adduct. All new compounds have been fully characterized by the usual analytical techniques as well as by X-ray analyses on selected examples.

Download Full-text

Substitution of a Hydroxy Group in a One-Pot Procedure

Category 3, Compounds with Four and Three Carbon Heteroatom Bonds ◽

10.1055/sos-sd-019-00138 ◽

2004 ◽

pp. 1

Author(s):

L. R. Subramanian

Keyword(s):

Hydroxy Group ◽

One Pot

Download Full-text

One-Pot Hydroxy Group Activation/Carbon-Carbon Bond Forming Sequence Using a Brønsted Base/Brønsted Acid System

Advanced Synthesis & Catalysis ◽

10.1002/adsc.201000602 ◽

2010 ◽

Vol 352 (17) ◽

pp. 2881-2886 ◽

Cited By ~ 33

Author(s):

Alice Devineau ◽

Guillaume Pousse ◽

Catherine Taillier ◽

Jérôme Blanchet ◽

Jacques Rouden ◽

...

Keyword(s):

Hydroxy Group ◽

Bronsted Acid ◽

Acid System ◽

Brønsted Acid ◽

One Pot ◽

Carbon Bond ◽

Bond Forming ◽

Carbon Carbon Bond ◽

Brönsted Acid ◽

Brønsted Base

Download Full-text

Synthesis and Antioxidant Activity of Caffeic Acid Derivatives

Molecules ◽

10.3390/molecules23092199 ◽

2018 ◽

Vol 23 (9) ◽

pp. 2199 ◽

Cited By ~ 14

Author(s):

Katarzyna Sidoryk ◽

Anna Jaromin ◽

Nina Filipczak ◽

Piotr Cmoch ◽

Marcin Cybulski

Keyword(s):

Organic Chemistry ◽

Antioxidant Activity ◽

Caffeic Acid ◽

Wittig Reaction ◽

Hydroxyl Group ◽

Hydroxyl Groups ◽

Water Medium ◽

One Pot ◽

Safe Alternative ◽

Caffeic Acid Derivatives

A series of caffeic acid derivatives were synthesized via a modified Wittig reaction which is a very important tool in organic chemistry for the construction of unsaturated carbon–carbon bonds. All reactions were performed in water medium at 90 °C. The aqueous Wittig reaction worked best when one unprotected hydroxyl group was present in the phenyl ring. The olefinations in the aqueous conditions were also conducted with good yields in the presence of two unprotected hydroxyl groups. When the number of the hydroxyl groups was increased to three, the reaction yields were worse, and the derivatives 12, 13, and 18 were obtained with 74%, 37%, and 70% yields, respectively. Nevertheless, the Wittig reaction using water as the essential medium is an elegant one-pot synthesis and a greener method, which can be a safe alternative for implementation in organic chemistry. The obtained compounds were tested for their antioxidant activity, and 12, 13, and 18 showed the highest activities. Moreover, all synthesized compounds displayed no cytotoxicity, and can therefore be used in the pharmaceutical or cosmetic industry.

Download Full-text

A metal-free biaryl coupling reaction activated by a sulfonium salt

Organic Chemistry Frontiers ◽

10.1039/c8qo00798e ◽

2018 ◽

Vol 5 (22) ◽

pp. 3219-3225 ◽

Cited By ~ 6

Author(s):

Kazuhiro Higuchi ◽

Takuhiro Tago ◽

Yusuke Kokubo ◽

Motoki Ito ◽

Masanori Tayu ◽

...

Keyword(s):

Coupling Reaction ◽

Sulfonium Salt ◽

One Pot ◽

Metal Free ◽

Trifluoromethanesulfonic Anhydride ◽

Biaryl Coupling ◽

Aryl Ethers

A metal-free biaryl coupling reaction of phenol or aryl ethers mediated by a sulfonium salt formed from diphenyl sulfoxide and trifluoromethanesulfonic anhydride has been developed. The method is a rapid, one-pot reaction, leaving no traces of the sulfonium moiety in the product.

Download Full-text

CuI/Et2NH-Catalyzed One-Pot Highly Efficient Synthesis of 1,4-Disubstituted 1,2,3-Triazoles in Green Solvent Glycerol

Synthesis ◽

10.1055/s-0036-1591557 ◽

2018 ◽

Vol 50 (11) ◽

pp. 2191-2199 ◽

Cited By ~ 4

Author(s):

Yongde Zhao ◽

Shengqiang Guo ◽

Yang Zhou ◽

Bencai Dai ◽

Cuimeng Huo ◽

...

Keyword(s):

Catalytic System ◽

Sodium Azide ◽

Room Temperature ◽

Green Solvent ◽

Efficient Synthesis ◽

One Pot ◽

Highly Efficient ◽

Three Component Reaction ◽

Efficient Route ◽

Terminal Acetylenes

A concise one-pot three-component reaction of organic halides, terminal acetylenes, and sodium azide provided an efficient route for the synthesis of 1,2,3-triazoles. A variety of 1,2,3-triazoles were prepared in good to excellent yields with green solvent glycerol. This procedure used CuI and diethylamine, which are two easily available reagents as the new catalytic system at room temperature.

Download Full-text