New synthetic approach to epoxyisoindolo[2,1-a]quinolines based on cycloaddition reactions of 2-furyl-substituted tetrahydroquinolines with maleic anhydride and acryloyl chloride

2007 ◽  
Vol 56 (5) ◽  
pp. 1063-1079 ◽  
Author(s):  
F. I. Zubkov ◽  
V. P. Zaitsev ◽  
A. S. Peregudov ◽  
N. M. Mikhailova ◽  
A. V. Varlamov
Keyword(s):  
Maleic Anhydride ◽  
Synthetic Approach ◽  
Acryloyl Chloride ◽  
Cycloaddition Reactions

Synthesis of functionalized hexahydro-, octahydro-, and decahydro-1H-phenalenes via Diels–Alder reactions of 1-methylene-4a-methoxycarbonyl-1,2,3,4,4a,5,6,7-octahydronaphthalene and related dienes

1993 ◽  
Vol 71 (9) ◽  
pp. 1463-1483 ◽  
Author(s):  
Edward Piers ◽  
Richard W. Friesen ◽  
Paul Kao ◽  
Steven J. Rettig ◽  
James Trotter
Keyword(s):  
Maleic Anhydride ◽  
Transition State ◽  
Methyl Acrylate ◽  
Diels Alder ◽  
Cycloaddition Reactions ◽  
Methoxycarbonyl Group ◽  
The Face ◽  
Group Reaction ◽  
Bicyclic Dienes

The results of a study of Diels–Alder reactions of the bicyclic dienes 6–8 with a variety of dienophiles are reported. Although 6 and 7 undergo cycloaddition reactions smoothly and efficiently, thermal Diels–Alder reactions of 8 are generally sluggish or, under the conditions investigated, do not proceed at all. Additions of tetracyanoethylene (TCNE) to 6–8 are highly face-selective, with preferential attack of the dienophile on the side of the dienes opposite to the angular methoxycarbonyl group. Reaction of 7 with maleic anhydride (MAN) is completely face-selective and proceeds preferentially via an endo transition state. Diels–Alder reactions of 6 and 7 with methyl acrylate (MAC) and nitroethylene (NE) are entirely regioselective, but the face-selectivities, which vary from ~2:1 to ~3:1, are rather low. The use of this chemistry as a method for the synthesis of functionalized, stereochemically defined, perhydro-1H-phenalenes is demonstrated.

Studying the effect of high pressure on the cycloaddition reactions of maleic anhydride and substituted anthracenes

2012 ◽  
Vol 87 (1) ◽  
pp. 160-162 ◽  
Author(s):  
V. D. Kiselev ◽  
I. I. Shakirova ◽  
D. A. Kornilov ◽  
E. A. Kashaeva ◽  
L. N. Potapova ◽  
...  
Keyword(s):  
High Pressure ◽  
Maleic Anhydride ◽  
Cycloaddition Reactions

Natural 1,2-Dithiolane 1-Oxides. A Synthetic Approach Based on [2+2]-Cycloaddition Reactions with Thiones

Synlett ◽  
1991 ◽  
Vol 1991 (09) ◽  
pp. 717-718
Author(s):  
Gerald Pattenden ◽  
Anthony J. Shuker
Keyword(s):  
Synthetic Approach ◽  
Cycloaddition Reactions

New Synthetic Approach to Substituted Isoindolo[2,1-a]quinoline Carboxylic Acids via Intramolecular Diels—Alder Reaction of 4-(Furyl-2)-4-arylaminobutenes-1 with Maleic Anhydride.

ChemInform ◽  
2005 ◽  
Vol 36 (34) ◽  
Author(s):  
Fedor I. Zubkov ◽  
Ekaterina V. Boltukhina ◽  
Konstantin F. Turchin ◽  
Roman S. Borisov ◽  
Alexey V. Varlamov
Keyword(s):  
Maleic Anhydride ◽  
Carboxylic Acids ◽  
Alder Reaction ◽  
Diels Alder ◽  
Synthetic Approach ◽  
Diels Alder Reaction

Intramolecular [4+2] cycloaddition of furfurylsubstituted homoallylamines to allylhalides, acryloyl chloride and maleic anhydride

2006 ◽  
Vol 43 (6) ◽  
pp. 1479-1495 ◽  
Author(s):  
Alexey V. Varlamov ◽  
Ekaterina V. Boltukhina ◽  
Fedor I. Zubkov ◽  
Eugenia V. Nikitina ◽  
Konstantin F. Turchin
Keyword(s):  
Maleic Anhydride ◽  
Acryloyl Chloride
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