scholarly journals One-Pot Green Catalytic Preparation of 3-Aminobenzoic Acid in the Presence of Carbonaceous Bio-Based Materials in Subcritical Water

2020 ◽  
Vol 2 (1) ◽  
pp. 16
Author(s):  
Sarra Tadrent ◽  
Christophe Len
Keyword(s):  
Nitro Group ◽  
Subcritical Water ◽  
Aminobenzoic Acid ◽  
Formyl Group ◽  
One Pot

A green and sustainable approach for the production of 3-aminobenzoic acid (3-ABA) from 3-nitrobenzaldehyde promoted by NORIT GAC 12-40 as a carbonaceous bio-based material was successfully achieved in subcritical water. The process involves two successive reactions: reduction of the nitro group and oxidation of the formyl group. At 300 °C under 90 bar for 6 h, the yield of 3-ABA is 59%.

Reductive Condensation of a Nitro Group with Carboxylic Acids Promoted by Phosphorus(III) Compounds: A Short Route to 5H-Dibenzo[b,e][1,4]diazepin-11(10H)-ones

Synthesis ◽  
2020 ◽  
Author(s):  
Zbigniew Wróbel ◽  
Michał Tryniszewski ◽  
Robert Bujok ◽  
Roman Gańczarczyk
Keyword(s):  
Nitro Group ◽  
Carboxylic Acids ◽  
Carboxyl Group ◽  
Short Route ◽  
Step Method ◽  
One Pot ◽  
Aryl Group ◽  
Intramolecular Condensation ◽  
Reductive Condensation

Tributyl- or triphenylphosphine promotes a one-pot, three-step method for the synthesis of differently substituted dibenzodiazepinones from N-aryl-2-nitroanilines. Pyridine analogues and the corresponding thiazepinones can also be formed using this method. The process involves deoxygenation of the nitro group, then formation of an iminophosphorane intermediate and its intramolecular condensation with a carboxyl group placed in the N-aryl group. The role of the carboxyl group in the formation of the iminophosphorane and the mode of cyclization are discussed.

Simple Synthesis of Fused Thiazolo[4,5-b]pyridines through Successive SNAr Processes

Synlett ◽  
2020 ◽  
Author(s):  
Alexey M. Starosotnikov ◽  
Maxim A. Bastrakov ◽  
Vadim V. Kachala ◽  
Ivan V. Fedyanin ◽  
Tatyana A. Klimova ◽  
...  
Keyword(s):  
Nucleophilic Substitution ◽  
Nitro Group ◽  
Chlorine Atom ◽  
Simple Synthesis ◽  
Smiles Rearrangement ◽  
One Pot

AbstractA convenient process is described for the synthesis of novel thiazolo[4,5-b]pyridines fused with triazole or pyrimidine rings. The base-promoted reactions of 2-chloro-3-nitropyridines with 1,3-(S,N)-binucleophiles (triazole-5-thiols, 4-oxopyrimidine-2-thiones) resulted in nucleophilic substitution of the chlorine atom and subsequent S–N-type Smiles rearrangement followed by nucleophilic substitution of the nitro group. Reactions with pyrimidine-2-thiones were carried out as one-pot processes while, in the case of triazole-5-thiols, isolation of intermediate substitution products was found to be preferable.

scholarly journals New fast “One-pot” Technique for the Production of Glycyrrhetinic Acid from the Roots of licorice (Glycyrrhiza glabra)

2018 ◽  
Vol 13 (7) ◽  
pp. 1934578X1801300
Author(s):  
Anna V. Lekar ◽  
Sergey N. Borisenko ◽  
Elena V. Vetrova ◽  
Elena V. Maksimenko ◽  
Salima S. Khizrieva ◽  
...  
Keyword(s):  
Organic Solvents ◽  
Subcritical Water ◽  
Low Cost ◽  
Glycyrrhetinic Acid ◽  
Glycyrrhiza Glabra ◽  
One Pot ◽  
Glycyrrhiza Glabra L ◽  
The One ◽  
Toxic Organic Solvents ◽  
Pot Technique

The aim of this work was to develop and study a fast “one-pot” procedure for the production of glycyrrhetinic acid (GLA) from the roots of licorice ( Glycyrrhiza glabra L.) using subcritical water (SBW). Technique requires no use expensive and toxic organic solvents. For the first time the new method was used for the production of glycyrrhetinic acid (aglycone of glycyrrhizic acid) by “one-pot” technique. HPLC was used to determine the quantitative compositions of the obtained products. It has been shown that variation of only one parameter of the process (temperature) allows alteration of composition of the products obtained by new “one-pot” technique. The “one-pot” procedure developed for the production of GLA in SBW is faster (12 folds) than conventional methods that use expensive and toxic organic solvents. The proposed procedure has the excellent potential for the future development of the fast and low cost technologies for the production of GLA and its derivatives in the pharmaceutical, food and cosmetic industries.

scholarly journals Synthesis and characterization of novel bioactive 1,2,4-oxadiazole natural product analogs bearing the N-phenylmaleimide and N-phenylsuccinimide moieties

2013 ◽  
Vol 9 ◽  
pp. 2202-2215 ◽  
Author(s):  
Catalin V Maftei ◽  
Elena Fodor ◽  
Peter G Jones ◽  
M Heiko Franz ◽  
Gerhard Kelter ◽  
...  
Keyword(s):  
Natural Product ◽  
Synthesis And Characterization ◽  
Aminobenzoic Acid ◽  
One Pot ◽  
X Ray ◽  
X Ray Crystallography ◽  
Quisqualic Acid ◽  
Oxobutanoic Acid

Taking into consideration the biological activity of the only natural products containing a 1,2,4-oxadiazole ring in their structure (quisqualic acid and phidianidines A and B), the natural product analogs 1-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenyl)pyrrolidine-2,5-dione (4) and 1-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenyl)-1H-pyrrole-2,5-dione (7) were synthesized starting from 4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)aniline (1) in two steps by isolating the intermediates 4-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenylamino)-4-oxobutanoic acid (3) and (Z)-4-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenylamino)-4-oxobut-2-enoic acid (6). The two natural product analogs 4 and 7 were then tested for antitumor activity toward a panel of 11 cell lines in vitro by using a monolayer cell-survival and proliferation assay. Compound 7 was the most potent and exhibited a mean IC50 value of approximately 9.4 µM. Aniline 1 was synthesized by two routes in one-pot reactions starting from tert-butylamidoxime and 4-aminobenzoic acid or 4-nitrobenzonitrile. The structures of compounds 1, 2, 4, 5 and 6 were confirmed by X-ray crystallography.

scholarly journals An Efficient Approach to 2-CF3-Indoles Based on ortho-Nitrobenzaldehydes

Molecules ◽  
2021 ◽  
Vol 26 (23) ◽  
pp. 7365
Author(s):  
Vasiliy M. Muzalevskiy ◽  
Zoia A. Sizova ◽  
Vladimir T. Abaev ◽  
Valentine G. Nenajdenko
Keyword(s):  
Nitro Group ◽  
Intramolecular Cyclization ◽  
One Pot ◽  
Efficient Approach ◽  
Catalytic Olefination Reaction

The catalytic olefination reaction of 2-nitrobenzaldehydes with CF3CCl3 afforded stereoselectively trifluoromethylated ortho-nitrostyrenes in up to 88% yield. The reaction of these alkenes with pyrrolidine permits preparation of α-CF3-β-(2-nitroaryl) enamines. Subsequent one pot reduction of nitro-group by Fe-AcOH-H2O system initiated intramolecular cyclization to afford 2-CF3-indoles. Target products can be prepared in up to 85% yields. Broad synthetic scope of the reaction was shown as well as some followed up transformations of 2- CF3-indole.

scholarly journals 6-Chloro-8-nitro-4-oxo-4H-chromene-3-carbaldehyde

2014 ◽  
Vol 70 (5) ◽  
pp. o547-o547
Author(s):  
Yoshinobu Ishikawa
Keyword(s):  
Hydrogen Bonds ◽  
Nitro Group ◽  
Title Compound ◽  
Formyl Group ◽  
Torsion Angles ◽  
Π Interactions ◽  
Compound C ◽  
Centroid Distance ◽  
Benzene Rings ◽  
The Mean

In the title compound, C10H4ClNO5, the non-H atoms of the 6-chlorochromone unit are coplanar (r.m.s. deviation = 0.017 Å) with the largest deviation from the mean plane [0.031 (2) Å] being found for the C=O C atom. The nitro group (NO2) is inclined to the chromone unit mean plane by 13.3 (2) °. The formyl group is also twisted with respect to the attached ring [C—C—C—O torsion angles = 10.8 (4) and −171.8 (2)°]. In the crystal, molecules are linked via C-H...O hydrogen bonds forming slab-like networks lying parallel to (-301). The slabs are linked by π–π interactions involving the benzene rings of the chromone units [centroid–centroid distance = 3.770 (3) Å].

“One-Pot” Technique for Transformation of the Aporphine Alkaloid Boldine into Phenanthrene Seco-Boldine with Subcritical Water

2020 ◽  
Vol 14 (7) ◽  
pp. 1153-1157
Author(s):  
A. V. Lekar’ ◽  
E. V. Maksimenko ◽  
S. N. Borisenko ◽  
S. S. Khizrieva ◽  
N. I. Borisenko ◽  
...  
Keyword(s):  
Subcritical Water ◽  
One Pot ◽  
Aporphine Alkaloid ◽  
Pot Technique

Dihydrobenzofuran production from catalytic tandem Claisen rearrangement–intramolecular hydroaryloxylation of allyl phenyl ethers in subcritical water

RSC Advances ◽  
2014 ◽  
Vol 4 (56) ◽  
pp. 29527-29533 ◽  
Author(s):  
Ligang Luo ◽  
Chunze Liu ◽  
Zhiqiang Hou ◽  
Yuanyuan Wang ◽  
Liyi Dai
Keyword(s):  
Claisen Rearrangement ◽  
Subcritical Water ◽  
One Pot ◽  
The One ◽  
Phenyl Ethers

The one pot rapid and high-yielding Claisen hydroaryloxylation of allyl phenyl ethers in subcritical water is described (see scheme).

One-Pot Synthesis of Glycyrrhetinic Acid from Licorice Root in Subcritical Water

2019 ◽  
Vol 13 (7) ◽  
pp. 1150-1154
Author(s):  
A. V. Lekar ◽  
E. V. Maksimenko ◽  
S. N. Borisenko ◽  
S. S. Khizrieva ◽  
E. V. Vetrova ◽  
...  
Keyword(s):  
Subcritical Water ◽  
Glycyrrhetinic Acid ◽  
Licorice Root ◽  
One Pot ◽  
One Pot Synthesis
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