Imino Diels–Alder reaction — An efficient synthetic protocol for 2-methyl-4-substituted tetrahydroquinolines catalyzed by copper dipyridine dichloride

2010 ◽  
Vol 88 (5) ◽  
pp. 443-452 ◽  
Author(s):  
C. S. Kavitha ◽  
K. M. Hosamani ◽  
R. S. Harisha
Keyword(s):  
Elemental Analysis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Reusable Catalyst ◽  
Substituted Anilines ◽  
H Nmr ◽  
Diels Alder Reaction ◽  
First Time ◽  
C Nmr

For the first time, copper dipyridine dichloride (CuPy2Cl2) is used as an efficient and reusable catalyst for the imino Diels–Alder reaction of para-substituted anilines with N-vinylpyrrolidinone, N-vinylcarbazole, and N-vinylcaprolactam in acetonitrile to afford the corresponding 2-methyl-4-substituted-1,2,3,4-tetrahydroquinoline derivatives in excellent yields with good purity. The products were characterized by FTIR, 1H NMR, 13C NMR, MS, and elemental analysis.

scholarly journals Synthesis and Evaluation of Substituted 4,4a-Dihydro-3H,10H-pyrano[4,3-b][1]benzopyran-10-one as Antimicrobial Agent

2013 ◽  
Vol 2013 ◽  
pp. 1-11 ◽  
Author(s):  
Amanpreet Kaur ◽  
Vishal Sharma ◽  
Abhishek Budhiraja ◽  
Harpreet Kaur ◽  
Vivek Gupta ◽  
...  
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Enol Ethers ◽  
Spectral Techniques ◽  
Mass Spectral ◽  
H Nmr ◽  
Diels Alder Reaction ◽  
Electron Withdrawing Group ◽  
Inhibitory Potential ◽  
C Nmr

A series of pyrano[4,3-b][1]benzopyranones (7a–t) were synthesized through hetero-Diels-Alder reaction of substituted 3-formylchromones (5) with enol ethers (6), characterized by IR, 1H NMR, 13C NMR, and mass spectral techniques. All the compounds were evaluated for antimicrobial activity against various bacterial and fungal strains, found to possess significant inhibitory potential, particularly, compounds bearing electron withdrawing group -fluoro such as 7i and 7h. Compounds were also tested and displayed a significant inhibitory potential against methicillin-resistant Staphylococcus aureus (MRSA).

Ring-Closing Metathesis Approach to Cage Propellanes Containing Oxepane and Tetrahydrofuran Hybrid System

Synthesis ◽  
2017 ◽  
Vol 49 (24) ◽  
pp. 5339-5350 ◽  
Author(s):  
Sambasivarao Kotha ◽  
Subba Cheekatla ◽  
Darshan Mhatre
Keyword(s):  
Claisen Rearrangement ◽  
Alder Reaction ◽  
Diels Alder ◽  
Ring Closing Metathesis ◽  
Cage Compounds ◽  
Transannular Cyclization ◽  
Diels Alder Reaction ◽  
Grignard Addition ◽  
Key Steps ◽  
First Time

The preparation of a variety of structurally interesting oxygenated cage compounds involving atom-economic processes such as Claisen rearrangement, Diels–Alder reaction, [2+2] photocycloaddition, and ring-closing metathesis (RCM) as key steps is reported. For the first time, oxepane ring system is introduced in cage framework using olefin metathesis as a key step. These cage systems assembled here are difficult to prepare by traditional methods. The synthetic sequence described here opens up new routes to higher order polycycles containing heteroatoms without the involvement of protecting groups. Transannular cyclization observed during Grignard addition and the RCM protocol used here may be applicable to generate unknown oxygenated cage systems.

Diels−Alder Reaction of 2-Amino-Substituted Furans as a Method for Preparing Substituted Anilines

1997 ◽  
Vol 62 (12) ◽  
pp. 4088-4096 ◽  
Author(s):  
Albert Padwa ◽  
Martin Dimitroff ◽  
Alex G. Waterson ◽  
Tianhua Wu
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Substituted Anilines ◽  
Diels Alder Reaction ◽  
Substituted Furans

Synthesis, Generic Dyeing of Nindigo Derivatives on Unmodified Polypropylene; First Time Application in Dyeing Technology

2019 ◽  
Vol 19 (11) ◽  
pp. 7105-7111 ◽  
Author(s):  
Raju Penthala ◽  
Rangaraju Satish Kumar ◽  
Hyorim Kim ◽  
Gisu Heo ◽  
Young-A Son
Keyword(s):  
Mass Spectrometry ◽  
Polypropylene Fiber ◽  
Blue Color ◽  
Substituted Anilines ◽  
Simple Route ◽  
H Nmr ◽  
Dispersing Agent ◽  
Didodecyldimethylammonium Bromide ◽  
First Time ◽  
C Nmr

Hydrophobic nindigo dyes were designed and successfully synthesized from indigo by reacting with substituted anilines in a simple route. Four nindigo dyes were fruitfully analyzed by 1H NMR 13C NMR, electronic and mass spectrometry. Here, we have firstly introduced these nindigo dyes into dyeing area for the dyeing of unmodified polypropylene fiber in aqueous medium. Dyeing experiments has been performed by using didodecyldimethylammonium bromide dispersing agent to make dye-dispersant complex for enhancing the dispersion of dyes. All the dyes were displayed profound blue color hue on polypropylene. The dyeing efficiency and dye fixation order of the nindigo dyes are 3d > 3c ≥ 3b > 3a. Compound 3d having higher the hydrophobic character (logP ═ 7.04), so greater the dye ability on the polypropylene fiber and exhibiting deep coloration.

Synthèse d'aryl nitronorbornènes par cycloaddition de Diels–Alder entre les aryl-nitroéthylènes et le cyclopentadiène. Justification de la stéréochimie et de la réactivité relative observées par la méthode CNDO/II. Obtention d'aryl aminonorbornènes

1985 ◽  
Vol 63 (9) ◽  
pp. 2354-2361 ◽  
Author(s):  
Jean Bourguignon ◽  
Gilles Le Nard ◽  
Guy Queguiner
Keyword(s):  
Theoretical Calculations ◽  
Alder Reaction ◽  
Diels Alder ◽  
Relative Reactivity ◽  
H Nmr ◽  
Diels Alder Reaction

Syntheses of numerous 2-aryl nitroethylenes (nitrostyrenes) have been optimized. The nitrostyrenes have been reacted with cyclopentadiene in Diels–Alder cycloadditions and the 3-aryl 2-nitronorbornenes obtained have been reduced into 3-aryl 2-aminonorbornenes. These compounds are potentially dopaminergic molecules. The stereochemistry of the adducts obtained in the Diels–Alder reaction has been determined by 1H nmr. The stereochemistry and the relative reactivity of the nitrostyrenes versus cyclopentadiene have been confirmed by theoretical calculations based on the CNDO/II method.

A new route for the synthesis of highly substituted 4-aminoquinoline drug like molecules via aza hetero–Diels–Alder reaction

2015 ◽  
Vol 13 (28) ◽  
pp. 7614-7618 ◽  
Author(s):  
Shinde Vidyacharan ◽  
A. Sagar ◽  
Duddu S. Sharada
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
First Time

A new route has been developed for the synthesis of 4-aminoquinoline drug like moleculesviaaza hetero–Diels–Alder reaction starting from 2H-indazole as a diene for the first time.

Synthesis and X-ray powder diffraction data of cis-4-(4-methoxyphenyl)-3-methyl-6-nitro-2-phenyl-1,2,3,4-tetrahydroquinoline

2013 ◽  
Vol 28 (4) ◽  
pp. 307-311 ◽  
Author(s):  
M.A. Macías ◽  
J.A. Henao ◽  
Arnold R. Romero Bohórquez ◽  
Vladimir V. Kouznetsov
Keyword(s):  
Powder Diffraction ◽  
Alder Reaction ◽  
Diels Alder ◽  
Gas Chromatography Mass Spectrometry ◽  
One Pot ◽  
X Ray ◽  
Cell Parameters ◽  
Diels Alder Reaction ◽  
The One ◽  
C Nmr

The 2,4-diaryl 1,2,3,4-tetrahydroquinoline derivative (1), described in the title (Chemical formula: C23H22N2O3), was synthesized via the “one-pot” three-component imino Diels–Alder reaction catalyzed by Cu(OTf)2. Molecular characterization was performed by 1H and 13C NMR, Fourier transform-infrared, and gas chromatography-mass spectrometry. The X-ray powder diffraction pattern for the title compound was analyzed and found to be crystallized in an orthorhombic system with space group P212121 (No. 19) and refined unit-cell parameters a = 8.6415(8) Å, b = 12.679(2) Å, c = 17.601(2) Å, and V = 1928.4(2) Å3.

Scandium trifluoromethanesulfonate (Sc(OTf)3). A novel reusable catalyst in the Diels-Alder reaction

1993 ◽  
Vol 34 (23) ◽  
pp. 3755-3758 ◽  
Author(s):  
Shū Kobayashi ◽  
Iwao Hachiya ◽  
Mitsuharu Araki ◽  
Haruro Ishitani
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Reusable Catalyst ◽  
Diels Alder Reaction

Enantioselective Diels-Alder reaction of (E)-1-trimethylsilyloxy-1,3-butadiene with chiral glyoxylates

1990 ◽  
Vol 55 (1) ◽  
pp. 230-244 ◽  
Author(s):  
Otakar Červinka ◽  
Aleš Svatoš ◽  
Petr Trška ◽  
Pavel Pech
Keyword(s):  
Nmr Spectroscopy ◽  
Quantum Chemical Calculations ◽  
Absolute Configuration ◽  
Quantum Chemical ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Chemical Correlation ◽  
The Absolute ◽  
C Nmr

Enantioselective Diels-Alder reaction of (E)-1-trimethylsilyloxy-1,3-butadiene (I) with chiral (-)-menthyl (II) and (-)-8-phenylmenthyl (III) glyoxylates in various solvents without or with catalysts was studied. The reactions gave a mixture of trans-and cis-isomers of (-)-menthyl (IV) and (-)-8-phenylmenthyl (V) 2-trimethylsilyloxy-5,6-dihydro-2H-pyran-6-carboxylates. The regioselectivity of the reaction was explained by quantum-chemical calculations, the enantioselectivity was determined using 13C NMR spectroscopy and the absolute configuration of the addition products was assigned on the basis of chemical correlation with (S)-(-)-dimethyl malate.

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