Synthesis and application of 3,4,7,8-tetrakis-exo-methylenecycloocta-1,5-diene as a versatile Diels–Alder diene: synthesis of V-shaped cyclooctatetraene fused acenes

2020 ◽  
Vol 18 (34) ◽  
pp. 6738-6744
Author(s):  
Savita Gadigennavar ◽  
Sethuraman Sankararaman
Keyword(s):  

Synthesis of 3,4,7,8-tetrakis-exo-methylenecycloocta-1,5-diene, has been reported. Diels-Alder reactions with this diene provides a shorter route for the synthesis of cyclooctatetraene fused with rigid aromatic wings.

2001 ◽  
Vol 79 (12) ◽  
pp. 1906-1909 ◽  
Author(s):  
Christopher K Jankowski ◽  
Gaëtan LeClair ◽  
Jacqueline MR Bélanger ◽  
Jocelyn RJ Paré ◽  
Marie-Rose VanCalsteren

The synthesis of isoquinolinone carboxylates was performed using arecoline or its isomer N-methyl tetrahydro pyridine carboxylate with Danishefsky's diene via thermal or microwave assisted Diels-Alder reaction. The comparison of both condensation modes showed that the microwave method not only afforded higher yields of the adducts, but also lead to the formation of a new α,β-unsaturated pyridyl ketone. All structures were identified with the help of high resolution 2D NMR.Key words: Diels-Alder microwave assisted reaction, microwave synthesis, Michael, diene, isoquinoline carboxylate synthesis, Danishefsky diene synthesis, MAP Diels-Alder2.


Tetrahedron ◽  
1996 ◽  
Vol 52 (18) ◽  
pp. 6325-6338 ◽  
Author(s):  
Teh-Chang Chou ◽  
Pao-Chiung Hong ◽  
Yane-Fong Wu ◽  
Wen-Yean Chang ◽  
Cheng-Tung Lin ◽  
...  

1942 ◽  
Vol 31 (2) ◽  
pp. 319-523 ◽  
Author(s):  
James A. Norton
Keyword(s):  

1947 ◽  
Vol 25b (3) ◽  
pp. 272-282 ◽  
Author(s):  
G. J. Janz ◽  
R. G. Ascah ◽  
A. G. Keenan

Cyanogen and butadiene have been found to react. The main product of the reaction was identified as 2-cyanopyridine. Some 2,2′-dipyridyl and a number of unidentified compounds were also found present in the product in small yields. No evidence for the presence of β-hydromucononitrile could be found. The reaction has been studied at atmospheric pressure in the vapour phase, and in ether solution, and at superatmospheric pressures in steel or glass bombs. In all cases the course of the reaction was essentially the same, 2-cyanopyridine being the main product. The formation of 2-cyanopyridine from butadiene and cyanogen is formulated as a Diels–Alder synthesis, in which the primary adduct undergoes a dehydrogenation to yield the final product. This is the first time to our knowledge that cyanogen has been reported as a dienophile in the diene synthesis.


1960 ◽  
Vol 25 (2) ◽  
pp. 276-278 ◽  
Author(s):  
Howard Burkett ◽  
William Wright
Keyword(s):  

Synlett ◽  
1989 ◽  
Vol 1989 (01) ◽  
pp. 30-32
Author(s):  
Thomas V. Lee ◽  
Alistair J. Leigh ◽  
Christopher B. Chapleo

2009 ◽  
Author(s):  
Pedro Mancini ◽  
Maria Kneeteman ◽  
Claudia Della Rosa
Keyword(s):  

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