A Simple, One-Pot Synthesis of Trans-Substituted Spiro [5,5] undecane-1,5,9-triones with Aromatic Aldehydes and Meldrum's Acid as the Starting Materials

2015 ◽  
Vol 68 (10) ◽  
pp. 1599 ◽  
Author(s):  
Jingping Ou-Yang ◽  
Yu Zhao ◽  
Huailei Jiang ◽  
Lingxin Meng ◽  
Xingshu Li ◽  
...  
Keyword(s):  
1H Nmr ◽  
Aromatic Aldehydes ◽  
Quantum Mechanical ◽  
Quantum Mechanical Calculations ◽  
Meldrum's Acid ◽  
X Ray Diffraction ◽  
Meldrum’S Acid ◽  
Reaction Conditions ◽  
One Pot ◽  
X Ray

A simple, one-pot process for the construction of substituted spiro[5,5]undecane-1,5,9-triones using aromatic aldehydes and Meldrum’s acid, and aniline as a catalyst, is reported. Fifteen compounds were synthesized, and the trans/cis ratios were calculated based on 1H NMR analyses of the unpurified products. Quantum mechanical calculations and X-ray diffraction were undertaken to identify the configuration of compound 2a. The proposed mechanisms for these reactions are presented in this paper. In contrast to previous literature, this method endows excellent diastereoselectivity to a series of trans-substituted derivatives. The method is characterized by its simple operation, commercial availability of all materials, mild reaction conditions and moderate-to-good chemical yields.

Crystal Forms of Semisynthetic Ergot Alkaloid Terguride

2002 ◽  
Vol 67 (4) ◽  
pp. 479-489 ◽  
Author(s):  
Michal Hušák ◽  
Bohumil Kratochvíl ◽  
Ivana Císařová ◽  
Ladislav Cvak ◽  
Alexandr Jegorov ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Ergot Alkaloid ◽  
Simplified Model ◽  
Quantum Mechanical ◽  
Quantum Mechanical Calculations ◽  
X Ray Diffraction ◽  
Torsion Angles ◽  
Crystal Forms ◽  
X Ray ◽  
Independent Molecules

Two new structures of semisynthetic ergot alkaloid terguride created by unusual number of symmetry-independent molecules were determined by X-ray diffraction methods at 150 K. Form A (monoclinic, P212121, Z = 12) contains three symmetry-independent terguride molecules and two molecules of water in the asymmetric part of the unit cell. The form CA (monoclinic, P21, Z = 8) is an anhydrate remarkable by the presence of four symmetry-independent molecules in the crystal structure. Conformations of twelve symmetry-independent molecules that were found in four already described terguride structures are compared with torsion angles obtained by ab initio quantum-mechanical calculations for the simplified model of N-cyclohexyl-N'-diethylurea.

Replacing sulfonate by carboxylate: application of pyridyliminocarboxylato copper(II) complexes in rac-lactide polymerization and Chan–Evans–Lam coupling

2019 ◽  
Vol 97 (3) ◽  
pp. 178-190 ◽  
Author(s):  
Valérie Hardouin Duparc ◽  
Clémentine Dimeck ◽  
Frank Schaper
Keyword(s):  
Molecular Sieves ◽  
Weight Control ◽  
Phenylboronic Acid ◽  
Side Reactions ◽  
X Ray Diffraction ◽  
Reaction Conditions ◽  
One Pot ◽  
X Ray ◽  
Induction Periods ◽  
Lactide Polymerization

Copper(II) complexes carrying pyridylmethyleneaminobenzoate or –propanoate ligands, LCuX, were prepared in one-pot reactions from pyridinecarboxaldehyde, aminobenzoic acid or β-alanine, and CuX2 (X = Cl, NO3, OAc, or OTf). All complexes were characterized by single-crystal X-ray diffraction studies and formed either dimers, tetramers, or coordination polymers. Attempted preparation of the respective alkoxide complexes, LCu(OR), was unsuccessful, but use of LCuX/NaOMe mixtures in rac-lactide polymerization indicated under some conditions coordination–insertion polymerization via a copper alkoxide as the mechanism. The complexes performed poorly in rac-lactide polymerization, showing low activities (12 h to completion at 140 °C), low to moderate heterotacticity (Pr = 0.6–0.8), and poor polymer molecular weight control (intramolecular transesterification). They were competent catalysts for Chan–Evans–Lam couplings with phenylboronic acid, without any indication of side reactions such as deboration or aryl homocoupling. The complexes were active in undried methanol, without addition of base, ligand, or molecular sieves. Aniline, n-octylamine, and cyclohexylamine were coupled quantitatively under identical reaction conditions. There is only little influence of the anion on activities (less than a factor of 2) but a strong influence on induction periods. The complexes were not active in CEL coupling with alcohols, phenols, or alkylboronic acids.

One-Pot Multicomponent Synthesis of Highly Functionalized Piperidines from Substituted β-Nitrostyrenes, Meldrum’s Acid, Aromatic Aldehydes, and Ammonium Acetate

2014 ◽  
Vol 16 (3) ◽  
pp. 113-119 ◽  
Author(s):  
Yan Li ◽  
Zhiheng Xue ◽  
Weijian Ye ◽  
Juanjuan Liu ◽  
Juan Yao ◽  
...  
Keyword(s):  
Ammonium Acetate ◽  
Aromatic Aldehydes ◽  
Meldrum's Acid ◽  
Multicomponent Synthesis ◽  
Meldrum’S Acid ◽  
One Pot

Three-component Reaction of Cycloheptanone, 6-Amino-1,3-Dimethyluracil and Aromatic Aldehydes; X-Ray Structure, and Anti-inflammatory Evaluation of the Products

2008 ◽  
Vol 63 (9) ◽  
pp. 1117-1126 ◽  
Author(s):  
Mohamed I. Hegab ◽  
Nasser A. Hassan ◽  
Farouk M. E. Abdel-Megeid
Keyword(s):  
Schiff Bases ◽  
Aromatic Aldehydes ◽  
X Ray Diffraction ◽  
Nmr Studies ◽  
Reaction Conditions ◽  
X Ray ◽  
Three Component Reaction ◽  
The Given ◽  
First Time ◽  
C Nmr

1,3-Dimethyl-5-aryl-1,6,7,8,9,10-hexahydrocyclohepta[5,6]pyrido[2,3-d]pyrimidine-2,4-diones 4a, b (the linear regioisomers) and the Schiff bases, 6-N-benzylidenamino-1,3-dimethyluracil derivatives 5a, b, were isolated from a three-component reaction of cycloheptanone, 6-amino-1,3- dimethyluracil, and 4-chloro- or 4-bromobenzaldehyde. Surprisingly, 1,3-dimethyl-10-aryl-1,5,6,7, 8,9-hexahydrocyclohepta[4,5]pyrido-[2,3-d]pyrimidine-2,4-diones 6f, g (the angular regioisomers which are described for the first time in the literature under the given reaction conditions) and the Schiff bases, 6-N-benzylidenamino-1,3-dimethyluracil derivatives 5f, g, were isolated and characterized from the reaction with 4-methoxybenzaldehyde and 4-cyanobenzaldehyde. However, the three-component reaction of 6-amino-1,3-dimethyluracil, cycloheptanone, and 2-methoxybenzaldehyde afforded 1,3-dimethylbenzo[4,5]pyrido[3,2-d]pyrimidine-3,4-dione (7). Single crystal X-ray diffraction and 13C NMR studies of 4a and 6f provided support for the established structures. Some of the new products were tested for antiinflammatory activity comparable to indomethacin.

A Novel Route for the Diastereoselective Synthesis of Dispiro[tetrahydroquinoline-bis(2,2-dimethyl[1,3]dioxane-4,6-dione)] Derivatives via a One-Pot Domino Multicomponent Reaction of Arylamines, Aromatic Aldehydes, and Meldrum's Acid

2014 ◽  
Vol 52 (3) ◽  
pp. 873-879 ◽  
Author(s):  
Mojtaba Lashkari ◽  
Malek Taher Maghsoodlou ◽  
Nourallah Hazeri ◽  
Sayyed Mostafa Habibi-Khorassani ◽  
Niloufar Akbarzadeh Torbati ◽  
...  
Keyword(s):  
Multicomponent Reaction ◽  
Aromatic Aldehydes ◽  
Diastereoselective Synthesis ◽  
Meldrum's Acid ◽  
Meldrum’S Acid ◽  
One Pot

One-Pot Synthesis of Trifluoromethylated Pyrazol-4-yl-pyrrole-2,5-dione Derivatives

Synthesis ◽  
2019 ◽  
Vol 51 (17) ◽  
pp. 3345-3355 ◽  
Author(s):  
Fangchong Yuan ◽  
Wenwen Duan ◽  
Zeyu Li ◽  
Xi Luo ◽  
Min Zhang ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Diffraction Analysis ◽  
Spectral Methods ◽  
Aromatic Aldehydes ◽  
X Ray Diffraction ◽  
One Pot ◽  
X Ray ◽  
Effect Of Solvents ◽  
Intramolecular Hydrogen ◽  
Strong Intramolecular Hydrogen Bond

Efficient and convenient one-pot, three-component reactions of pyrrolidone, aromatic aldehydes and 1-phenyl-3-trifluoromethyl-5-pyrazolone afforded highly functionalized trifluoromethylated pyrazol-4-ylpyrrole-2,5-dione derivatives in good yields. The effect of solvents on the reaction efficiency and yield was briefly investigated. The structures of products were determined by spectral methods and X-ray diffraction analysis. The latter showed that the products formed have a strong intramolecular hydrogen bond, which made them particularly stable and the corresponding annulated products were not obtained by treatment with dehydrating reagents.

scholarly journals Synthesis, Characterization, Crystallographic Studies of 5-Acetyl-8-hydroxyquinoline and Their Chalcone Derivatives

2020 ◽  
Vol 32 (7) ◽  
pp. 1609-1613
Author(s):  
C.B. Vagish ◽  
Karthik Kumara ◽  
N.K. Lokanath ◽  
K. Ajay Kumar ◽  
P.G. Chandrasherkar
Keyword(s):  
Single Crystal ◽  
Benzoyl Chloride ◽  
Condensation Reaction ◽  
Aromatic Aldehydes ◽  
Spectral Studies ◽  
Monoclinic Crystal System ◽  
X Ray Diffraction ◽  
Monoclinic Crystal ◽  
One Pot ◽  
X Ray

An efficient, easy and one pot synthesis for the Friedel-Craft acetylation reaction of quinolines was developed. The reaction between 8-hydroxyquinoline and acetyl/benzoyl chloride in nitrobenzene immediately flocculates as yellow precipitate. On further addition of Lewis acid causes the Friedel-Craft acetylation leads to formation of acetylated quionlines in good yields. The structure of compound 5-acetyl-8-hydroxyquinoline (3) was confirmed by single crystal X-ray diffraction studies. The compound crystallizes in the monoclinic crystal system with the space group P21/c. The synthesized acetylated quionlines undergoes condensation reaction with aromatic aldehydes leads to 8-hydroxyquinoline chalcones derivatives. The products were characterized by spectral studies, elemental analysis and single crystal X-ray diffraction studies.

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