Diethyl Azodicarboxylate-Promoted Oxidative [3 + 2] Cycloaddition for the Synthesis of Pyrrolo[2,1-a]isoquinolines

2020 ◽  
Vol 86 (1) ◽  
pp. 91-102
Author(s):  
Ya-Wen Xu ◽  
Jiankun Wang ◽  
Guangji Wang ◽  
Le Zhen
Keyword(s):  
Diethyl Azodicarboxylate

ChemInform Abstract: Highly Stereoselective Synthesis of cis-β-Enaminones Mediated by Diethyl Azodicarboxylate.

ChemInform ◽  
2012 ◽  
Vol 43 (22) ◽  
pp. no-no
Author(s):  
Xiaoliang Xu ◽  
Ping Du ◽  
Dongping Cheng ◽  
Hong Wang ◽  
Xiaonian Li
Keyword(s):  
Stereoselective Synthesis ◽  
Diethyl Azodicarboxylate

THE REACTION OF DIETHYL AZODICARBOXYLATE WITH DIHYDROGELSEMINE

1955 ◽  
Vol 33 (4) ◽  
pp. 604-609 ◽  
Author(s):  
Thelma Habgood ◽  
Léo Marion
Keyword(s):  
Infrared Spectrum ◽  
Methyl Ether ◽  
Sodium Borohydride ◽  
Lithium Aluminum Hydride ◽  
Chromic Acid ◽  
Aluminum Hydride ◽  
Membered Ring ◽  
Lithium Aluminum ◽  
Diethyl Azodicarboxylate ◽  
Methylene Group

Dihydrogelsemine reacts with diethyl azodicarboxylate yielding a carbinolamine which forms a methyl ether. Both this ether and the carbinolamine base can be oxidized by chromic acid to the same neutral lactam. That there has been no rearrangement of the carbon skeleton during these reactions is shown by reduction of the methyl ether of the carbinolamine with sodium borohydride to dihydrogelsemine and by reduction of the lactam with lithium aluminum hydride to tetrahydrodesoxygelsemine. It is concluded that both dihydrogelsemine and gelsemine contain a methylene group adjacent to N(b), and from the infrared spectrum of the lactam of dihydrogelsemine, N(b) appears to be part of a five-membered ring.

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