Cleavage of benzyloxycarbonyl-5-oxazolidinones to α-benzyloxycarbonylamino-α-alkyl esters by alcohols and sodium hydrogen carbonate

2001 ◽  
Vol 42 (31) ◽  
pp. 5319-5321 ◽  
Author(s):  
Pietro Allevi ◽  
Giuliana Cighetti ◽  
Mario Anastasia
Keyword(s):  
Sodium Hydrogen Carbonate ◽  
Alkyl Esters ◽  
Sodium Hydrogen ◽  
Hydrogen Carbonate

scholarly journals Experiments towards the Synthesis of the Ergot Alkaloids and Related Structures. Part 7.1 Novel Syntheses of some 4-Acyl-2,3,4,4a,5,6-hexahydrobenzo[f]quinolin-2-ones

1999 ◽  
Vol 23 (2) ◽  
pp. 94-95
Author(s):  
Mark A. E. Bowman ◽  
Ralph E. Bowman
Keyword(s):  
Sodium Hydrogen Carbonate ◽  
Ergot Alkaloids ◽  
Aqueous Sodium ◽  
Sodium Hydrogen ◽  
Hydrogen Carbonate ◽  
Aqueous Sodium Hydrogen Carbonate

Reaction of the N-formyl enol-lactone 4 and the corresponding N-acetyl 10 and N-methoxycarbonyl 11 derivatives with bis(trimethylsilyl)potassiomalonate in THF at 60°C followed by treatment with aqueous sodium hydrogen carbonate and cyclisation as above, yielded the 4-formyl-, 4-acetyl- and 4-methoxycarbonyl-tricyclic ketones 7, 13 and 14 in yields of 31, 35 and 36%, respectively.

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