Proline triflate catalysed Diels–Alder reaction in the synthesis of tetrahydroquinoline derivatives

2009 ◽  
Vol 2009 (8) ◽  
pp. 499-504 ◽  
Author(s):  
Jianjun Li ◽  
Jia Li ◽  
Weike Su
Keyword(s):  
Aromatic Amines ◽  
Alder Reaction ◽  
Diels Alder ◽  
One Pot ◽  
One Pot Synthesis ◽  
Diels Alder Reaction ◽  
The One ◽  
High Stereoselectivity

Proline triflate was found to catalyse efficiently the one-pot synthesis of 2H-pyranotetrahydroquinolines from aryl imines, and 3,4-dihydro-2 H-pyran with high stereoselectivity. The aryl imines were formed in situ from aromatic amines and arylaldehydes.

Facile One-Pot Synthesis and Crystal Structure of 2:1 Adducts of Myrcene (or Ocimene) with Benzoquinones

2020 ◽  
Vol 17 (8) ◽  
pp. 624-627
Author(s):  
Sujata V. Bhat ◽  
Rohan S. Pawar ◽  
P. Rajakannu
Keyword(s):  
Crystal Structure ◽  
Single Crystal ◽  
Alder Reaction ◽  
Diels Alder ◽  
One Pot ◽  
Synthesis And Crystal Structure ◽  
X Ray ◽  
One Pot Synthesis ◽  
Diels Alder Reaction

One-pot tandem oxidation and double Diels-Alder reaction of myrcene or ocimene with in situ generated 1,4-benzoquinone or 1,2-benzoquinone at 0°C for 1.5 h yielded polyalkylated 1,4,4a,5,8,8a,9a,10a-octahydro-9,10-anthracenediones and bis(alkylated) 9,10-phenanthrenedione respectively. The structure of novel bis-adduct from ocimene, (1R,4aR,5S,8aS,9aS,10aR)-rel- 1,4,4a,5,8,8a,9a,10a-octahydro-2,6-dimethyl-1,5-bis(3-methyl-2-buten-1-yl)-9,10-anthracenedione, was elucidated through single crystal X-ray analysis.

scholarly journals Preparación simple de nuevas N-(6-metil-2-nitrofenil-1,2,3,4-tetrahidroquinolin-4-il) pirrolidin-2-onas y su análisis espectroscópico. Objetivos.

2011 ◽  
Vol 16 (2) ◽  
pp. 160 ◽  
Author(s):  
John H. Bermudez ◽  
José Luis Pinto ◽  
Carlos Mario Meléndez ◽  
José A. Henao ◽  
Vladimir V. Kouznetsov
Keyword(s):  
Cycloaddition Reaction ◽  
2D Nmr ◽  
Alder Reaction ◽  
Diels Alder ◽  
Nmr Studies ◽  
One Pot ◽  
Isolation And Purification ◽  
One Pot Synthesis ◽  
Diels Alder Reaction ◽  
The One

<p><strong>Objectives. </strong>To prepare new N-(1,2,3,4-tetrahydroquinolin-4-yl) pyrrolidin-2-one molecules and to characterize them by spectroscopic methods. <strong>Materials and methods. </strong>All reagents were purchased from Aldrich, commercial grade. The purity of the products and the composition of the reaction mixtures were monitored by thin layer chromatography over Silufol UV<sub>254</sub> chromatoplates (0.25 mm). Product isolation and purification were performed by column chromatography (SiO<sub>2</sub>), using ethyl acetate. <strong>Results.</strong> Preparation of new N-(2-nitrophenyl-1,2,3,4-tetrahydroquinolin-4-yl) pyrrolidin-2-ones has been achieved via the one-pot synthesis, based on a BiCl<sub>3</sub>-catalyzed imino Diels-Alder cycloaddition reaction of toluidine, N-vinylpyrrolidin-2-one and 4-nitro- or 3-nitrobenzaldehydes. The structure of the pyrrolidine derivatives was confirmed by <sup>1</sup>H nmr and <sup>13</sup>C nmr studies, in addition to inverse-detected 2D NMR experiments and monocrystal X-ray diffraction. <strong>Conclusions. </strong>An efficient, economic, and fast synthetic route (multi-component imino Diels-Alder reaction) was employed in the construction of several new tetrahydroquinoline derivatives, useful and attractive rigid skeleton with well-defined stereochemistry.</p> <p> </p> <p><strong>Key words: </strong>tetrahydroquinoline derivatives, N-substituted pyrrolidin-2-ones, three component imino Diels-Alder reaction, one-pot synthesis.</p>

scholarly journals One-pot cross-enyne metathesis (CEYM)–Diels–Alder reaction of gem-difluoropropargylic alkynes

2013 ◽  
Vol 9 ◽  
pp. 2688-2695 ◽  
Author(s):  
Santos Fustero ◽  
Paula Bello ◽  
Javier Miró ◽  
María Sánchez-Roselló ◽  
Günter Haufe ◽  
...  
Keyword(s):  
Research Group ◽  
Alder Reaction ◽  
Diels Alder ◽  
Internal Source ◽  
Enyne Metathesis ◽  
One Pot ◽  
Diels Alder Reaction ◽  
Heterocyclic Derivatives ◽  
The One

Propargylic difluorides 1 were used as starting substrates in a combination of cross-enyne metathesis and Diels–Alder reactions. Thus, the reaction of 1 with ethylene in the presence of 2nd generation Hoveyda–Grubbs catalyst generates a diene moiety which in situ reacts with a wide variety of dienophiles giving rise to a small family of new fluorinated carbo- and heterocyclic derivatives in moderate to good yields. This is a complementary protocol to the one previously described by our research group, which involved the use of 1,7-octadiene as an internal source of ethylene.

Catalytic Imino Diels—Alder Reaction by Triflic Imide and Its Application to One-Pot Synthesis from Three Components.

ChemInform ◽  
2007 ◽  
Vol 38 (14) ◽  
Author(s):  
Kiyosei Takasu ◽  
Naoya Shindoh ◽  
Hidetoshi Takuyama ◽  
Masataka Ihara
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
One Pot ◽  
One Pot Synthesis ◽  
Diels Alder Reaction ◽  
Three Components

scholarly journals One-Pot Synthesis of 5,6-Dihydro-4H-1,2-Oxazines by Cyclization of Ketoximes with Derivatives of Allylbenzene

2010 ◽  
Vol 6 (1) ◽  
pp. 884-890
Author(s):  
Raad Kasim Yahya ◽  
K. M. Lokanatha Rai ◽  
Ebraheem Abdu Musad ◽  
P. T. Sowmya
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
One Pot ◽  
One Pot Synthesis ◽  
Diels Alder Reaction ◽  
Chloramine T ◽  
Derivatives Of

A new series of 5,6-dihydro-4H-1,2-oxazines were synthesized via hetero Diels-Alder reaction of  α-nitrosolefins with derivatives of allylbenzene. α-Nitrosoolefins were generated from ketoximes by the action of chloramine-T and triethylamine.

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