Regioselective cross-coupling reactions in the synthesis of multisubstituted purine bases and nucleosides

2005 ◽  
Author(s):  
Michal Hocek ◽  
Dana Hocková
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
Purine Bases ◽  
Cross Coupling Reactions

Synthesis of 6-Amino-, 6-Methyl- and 6-Aryl-2-(hydroxymethyl)purine Bases and Nucleosides

2006 ◽  
Vol 71 (6) ◽  
pp. 788-803 ◽  
Author(s):  
Peter Šilhár ◽  
Radek Pohl ◽  
Ivan Votruba ◽  
Blanka Klepetářová ◽  
Michal Hocek
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
Purine Derivatives ◽  
Purine Bases ◽  
Arylboronic Acids ◽  
Cross Coupling Reactions ◽  
Zinc Iodide

An efficient methodology of the synthesis of 6-substituted 2-(hydroxymethyl)purine derivatives (bases and nucleosides) was developed. Regioselective Pd-catalyzed cross-coupling reactions of 6-chloro-2-iodopurines with [(benzoyloxy)methyl]zinc iodide gave 2-[(benzoyloxy)-methyl]-6-chloropurines that were converted to 2-(hydroxymethyl)adenines by reactions with ammonia and to 6-methyl- or 6-aryl-2-(hydroxymethyl)purines by cross-coupling reactions with trimethylaluminium or arylboronic acids followed by deprotection. The title 6-substituted 2-(hydroxymethyl)purine bases and nucleosides did not exhibit significant cytostatic or anti-HCV activity.

New developments in direct functionalization of C–H and N–H bonds of purine bases via metal catalyzed cross-coupling reactions

RSC Advances ◽  
2015 ◽  
Vol 5 (55) ◽  
pp. 44371-44389 ◽  
Author(s):  
Morteza Abdoli ◽  
Zohreh Mirjafary ◽  
Hamid Saeidian ◽  
Ali Kakanejadifard
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
New Developments ◽  
Purine Bases ◽  
Cross Coupling Reactions ◽  
Concise Overview ◽  
Direct Functionalization ◽  
The Cross ◽  
Metal Catalyzed

This review provides a concise overview on the cross-coupling reactions in direct functionalization of purine bases in recent years.

Synthesis of 2-Substituted 6-(Hydroxymethyl)purine Bases and Nucleosides

2005 ◽  
Vol 70 (10) ◽  
pp. 1669-1695 ◽  
Author(s):  
Peter Šilhár ◽  
Radek Pohl ◽  
Ivan Votruba ◽  
Michal Hocek
Keyword(s):  
Adenosine Deaminase ◽  
Cross Coupling ◽  
The Other ◽  
Coupling Reactions ◽  
Purine Derivatives ◽  
Cytostatic Effect ◽  
Purine Bases ◽  
Cross Coupling Reactions ◽  
Zinc Iodide

A facile and efficient methodology of the synthesis of 6-(hydroxymethyl)purine derivatives (bases and nucleosides) was developed based on Pd-catalyzed cross-coupling reactions of 6-halopurines or N-protected 2-amino-6-halopurines with (benzoyloxymethyl)zinc iodide followed by deprotection. Regioselective hydroxymethylations of 2,6-dihalopurines were also studied and used for the synthesis of 2-chloro-6-(hydroxymethyl)- or 2,6-bis(hydroxymethyl)purines. The 6-(hydroxymethyl)purine ribonucleoside 5f exerted high cytostatic effect and moderate inhibition of adenosine deaminase, while all the other derivatives were much less effective or entirely inactive.

scholarly journals Synthesis of (purin-6-yl)acetates and their transformations to 6-(2-hydroxyethyl)- and 6-(carbamoylmethyl)purines

2009 ◽  
Vol 74 (7-8) ◽  
pp. 1035-1059 ◽  
Author(s):  
Zbyněk Hasník ◽  
Radek Pohl ◽  
Blanka Klepetářová ◽  
Michal Hocek
Keyword(s):  
Antiviral Activity ◽  
Cross Coupling ◽  
Significant Activity ◽  
Coupling Reactions ◽  
Nucleophilic Substitutions ◽  
Purine Bases ◽  
Cross Coupling Reactions ◽  
Novel Approach ◽  
Reformatsky Reagent ◽  
Activity Screening

A novel approach to the synthesis of (purin-6-yl)acetates was developed based on Pd-catalyzed cross-coupling reactions of 6-chloropurines with a Reformatsky reagent. Their reduction with NaBH4 and treatment with MnO2 gave 6-(2-hydroxyethyl)purines, while reactions with amines in presence of NaCN afforded 6-(carbamoylmethyl)purines. Mesylation of the 6-(2-hydroxyethyl)purines followed by nucleophilic substitutions gave rise to several 6-(2-substituted ethyl)purines. This methodology was successfully applied to the synthesis of substituted purine bases and nucleosides for cytostatic and antiviral activity screening. None of the compounds exerted significant activity.

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