ChemInform Abstract: The Dakin-West Reaction of N-Acyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylic Acids Using Trifluoroacetic Anhydride: Structural Revision for the Unexpected Product.

ChemInform ◽  
2010 ◽  
Vol 29 (27) ◽  
pp. no-no
Author(s):  
M. KAWASE ◽  
Y. OKADA ◽  
H. MIYAMAE
Keyword(s):  
Carboxylic Acids ◽  
Trifluoroacetic Anhydride ◽  
Structural Revision ◽  
Unexpected Product

scholarly journals Synthesis of 2,2'-Dipyrryl Ketones from Pyrrole-2-carboxylic Acids with Trifluoroacetic Anhydride

2013 ◽  
Vol 34 (9) ◽  
pp. 2604-2608 ◽  
Author(s):  
Se Hee Kim ◽  
Jin Woo Lim ◽  
Jin Yu ◽  
Jae Nyoung Kim
Keyword(s):  
Carboxylic Acids ◽  
Trifluoroacetic Anhydride

ChemInform Abstract: Synthesis of 2,2′-Dipyrryl Ketones from Pyrrole-2-carboxylic Acids with Trifluoroacetic Anhydride.

ChemInform ◽  
2014 ◽  
Vol 45 (7) ◽  
pp. no-no
Author(s):  
Se Hee Kim ◽  
Jin Woo Lim ◽  
Jin Yu ◽  
Jae Nyoung Kim
Keyword(s):  
Carboxylic Acids ◽  
Trifluoroacetic Anhydride

Access to Highly Substituted Pyrimidine N-Oxides and 4-Acetoxymethyl-Substituted Pyrimidines via the LANCA Three-Component Reaction–Cyclocondensation Sequence

Synthesis ◽  
2021 ◽  
Author(s):  
Reinhold Zimmer ◽  
Hans-Ulrich Reissig ◽  
Luise Schefzig ◽  
Timon Kurzawa ◽  
Giaime Rancan ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Room Temperature ◽  
Hydroxylamine Hydrochloride ◽  
Trifluoroacetic Anhydride ◽  
Pyrimidine Derivatives ◽  
Mild Conditions ◽  
Structural Variety ◽  
Three Component Reaction ◽  
Sterically Demanding ◽  
Synthetic Utility

AbstractThe LANCA three-component reaction of lithiated alkoxy­allenes (LA), nitriles (N), and carboxylic acids (CA) smoothly provides β-alkoxy-β-ketoenamides in broad structural variety. The subsequent cyclocondensation of these compounds with hydroxylamine hydrochloride afforded a large library of pyrimidine N-oxides under mild conditions and in good yields. Their synthetic utility was further increased by the Boekelheide rearrangement leading to 4-acetoxymethyl-substituted pyrimidines. With trifluoroacetic anhydride the rearrangement proceeds even at room temperature and directly furnishes 4-hydroxymethyl-substituted pyrimidine derivatives. The key reactions are very robust and work well even in the presence of sterically demanding substituents.

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