New recyclization reaction in the imidazo[4,5-c]pyridine series

1982 ◽  
Vol 18 (5) ◽  
pp. 540-540
Author(s):  
Yu. M. Yutilov ◽  
I. A. Svertilova
Keyword(s):  
Recyclization Reaction ◽  
Pyridine Series

[5-(Adenin-9-yl)-5-deoxy-L-pentofuranosyl]phosphonates - A Novel Type of Nucleotide Analogs Related to HPMPA. II. Synthesis of L-ribo and L-xylo Configurated Derivatives by Recyclization of Diethyl (5-RS)-[1,2-O-Isopropylidene-5-O-methanesulfonyl-D-pentofuranos-5-C-yl]phosphonates under Acidic Conditions

1993 ◽  
Vol 58 (9) ◽  
pp. 2180-2196 ◽  
Author(s):  
Miroslav Otmar ◽  
Ivan Rosenberg ◽  
Milena Masojídková ◽  
Antonín Holý
Keyword(s):  
Phosphonic Acid ◽  
Trifluoroacetic Acid ◽  
Recyclization Reaction ◽  
Nucleotide Analogs ◽  
Acidic Conditions

Further cyclic analogs of the antiviral (S)-9-(3-hydroxy-2-phosphonomethoxypropyl)adenine (I) were prepared: both anomers of [5-(adenin-9-yl)-5-doxy-L-ribofuranosyl]phosphonic acid (α-IId and β-IId) and [5-(adenin-9-yl)-5-doxy-α-L-ribofuranosyl]phosphonic acid (IIe). Recyclization reaction of diethyl (5RS-(3-O-benzyl-1,2-O-isopropylidene-5-O-methanesulfonyl-D-ribofuranos-5-C-yl)phosphonate (IVb) and diethyl (5RS-(3-O-benzyl-1,2-O-isopropylidene-5-O-methanesulfonyl-D-xylofuranos-5-C-yl)phosphonate (IVd) in trifluoroacetic acid led to cyclic aldehydes Va and Vb which were reduced to diethyl α- and β-L-ribofuranosylphosphonates VIb and α-L-xylofuranosylphosphonate VIIb. Conversion to the protected 5-O-tosylates VId and VIId, followed by reaction with adenine and deprotection, afforded the mentioned nucleotide analogs IId and IIe. An attempt to prepare L-pentofuranosylphosphonates Vc and XIII, suitable for the synthesis of nucleotide analogs of 3-deoxy-L-erythro and L-xylo configuration (IIf and IIg, respectively) by the recyclization reaction of the corresponding 5-O-methanesulfonyl derivatives IVf and XIIb failed. In this case, anhydro derivatives IXa, XVa and XVIa were isolated and identified.

Studies in the pyridine series. XXV. Dissociation constants of some piperidine and piperideine bases

1968 ◽  
Vol 33 (6) ◽  
pp. 1700-1708 ◽  
Author(s):  
J. Lakomý ◽  
A. Šilhánková ◽  
M. Ferles ◽  
O. Exner
Keyword(s):  
Dissociation Constants ◽  
Pyridine Series
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