Cross-coupling reactions of 2-amino-6-halopurine derivatives with organometallic reagents leading to 6-alkylated purine acyclic nucleotide analogues

1999 ◽  
Author(s):  
Michal Česnek ◽  
Michal Hocek ◽  
Antonín Holý
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
Nucleotide Analogues ◽  
Organometallic Reagents ◽  
Cross Coupling Reactions

Synthesis of Acyclic Nucleotide Analogues Derived from 6-Hetarylpurines via Cross-Coupling Reactions of 9-[2-(Diethoxyphosphonylmethoxy)ethyl]-6-iodopurine with Hetaryl Organometallic Reagents

1997 ◽  
Vol 62 (1) ◽  
pp. 136-146 ◽  
Author(s):  
Michal Hocek ◽  
Milena Masojídková ◽  
Antonín Holý
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
Nucleotide Analogues ◽  
Organometallic Reagents ◽  
Cross Coupling Reactions ◽  
Adenine Derivative

The title acyclic nucleotide analogues derived from 6-hetarylpurines were prepared by Pd(0)-catalysed cross-coupling reactions of 9-[2-(diethoxyphosphonylmethoxy)ethyl]-6-iodopurine (1) with hetarylorganometallics: (pyridin-2-yl)-, (imidazol-2-yl)- and (pyrrol-2-yl)zinc chlorides or (imidazol-5-yl)- stannanes, followed by deprotection in fair to good yields. The starting 6-iodopurine derivative 1 was prepared by iododeamination of the adenine derivative.

Synthesis of Acyclic Nucleotide Analogues Derived from 2-Amino-6-C-substituted Purines via Cross-Coupling Reactions of 2-Amino-9-{2-[(diisopropoxyphosphoryl)methoxy]ethyl}-6-halopurines with Diverse Organometallic Reagents

2000 ◽  
Vol 65 (8) ◽  
pp. 1357-1373 ◽  
Author(s):  
Michal Česnek ◽  
Michal Hocek ◽  
Antonín Holý
Keyword(s):  
Ion Exchange ◽  
Cross Coupling ◽  
Ion Exchange Chromatography ◽  
Exchange Chromatography ◽  
Cytostatic Activity ◽  
Coupling Reactions ◽  
Nucleotide Analogues ◽  
Organometallic Reagents ◽  
Arylboronic Acids ◽  
Cross Coupling Reactions

Cross-coupling reactions of 2-amino-6-chloro-9-{2-[(diisopropoxyphosphoryl)methoxy]ethyl}purine (1) and 2-amino-9-{2-[(diisopropoxyphosphoryl)methoxy]ethyl}-6-iodopurine (2) with diverse types of organometallic reagents have been studied. Arylboronic acids reacted with 1 to give the corresponding 2-amino-6-arylpurines 3a-3d in good yields. Analogously, trialkylaluminium reagents were used for the preparation of 6-alkyl-2-aminopurines 3k and 3l from 1. Hetarylzinc halides and hetarylstannanes required the use of 2-amino-6-iodopurine 2 to give the corresponding 2-amino-6-hetarylpurines 3e-3j in fair to good yields. A CuI/KF mediated coupling of perfluoroalkylsilanes with 2 afforded the 2-amino-6-perfluoroalkylpurines 3m and 3n in moderate yields. Cleavage of the esters 3 with bromo(trimethyl)silane gave the target free phosphonates 4 that were purified by ion- exchange chromatography. The title compounds were tested on antiviral and cytostatic activity.

scholarly journals α-Arylation of Amides from α-Halo Amides Using Metal-Catalyzed Cross-Coupling Reactions

Synthesis ◽  
2018 ◽  
Vol 51 (01) ◽  
pp. 178-184 ◽  
Author(s):  
E. Barde ◽  
A. Guérinot ◽  
J. Cossy
Keyword(s):  
Palladium Catalysis ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Nickel Catalysis ◽  
Organometallic Reagents ◽  
Iron Catalysis ◽  
Cross Coupling Reactions ◽  
Metal Catalyzed

Metal-catalyzed α-arylation of amides from α-halo amides with organometallic reagents is reviewed. The article includes Suzuki–Miyaura, Kumada–Corriu, Negishi, and Hiyama cross-coupling reactions.1 Introduction2 Suzuki–Miyaura Cross-Coupling2.1 Palladium Catalysis2.2 Nickel Catalysis3 Kumada–Corriu Cross-Coupling3.1 Nickel Catalysis3.2 Iron Catalysis3.3 Cobalt Catalysis4 Negishi Cross-Coupling5 Hiyama Cross-Coupling6 Conclusion

Are Organozirconium Reagents Applicable in Current Organic Synthesis?

Synthesis ◽  
2020 ◽  
Author(s):  
Ivana Némethová ◽  
Radovan Šebesta
Keyword(s):  
Cross Coupling ◽  
Short Review ◽  
Coupling Reactions ◽  
Conjugate Additions ◽  
Organometallic Reagents ◽  
Practical Applications ◽  
Cross Coupling Reactions ◽  
Allylic Substitutions ◽  
Schwartz Reagent ◽  
Polar Functional Groups

AbstractThe search for mild, user-friendly, easily accessible, and robust organometallic reagents is an important feature of organometallic chemistry. Ideally, new methodologies employing organometallics should be developed with respect to practical applications in syntheses of target compounds. In this short review, we investigate if organozirconium reagents can fulfill these criteria. Organozirconium compounds are typically generated via in situ hydrozirconation of alkenes or alkynes with the Schwartz reagent. Alkyl and alkenylzirconium reagents have proven to be convenient in conjugate additions, allylic substitutions, cross-coupling reactions, and additions to carbonyls or imines. Furthermore, the Schwartz reagent itself is a useful reducing agent for polar functional groups.1 Introduction2 Synthesis and Generation of the Schwartz Reagent3 Structure and Properties of Cp2Zr(H)Cl4 Reactivity of Organozirconium Reagents4.1 Asymmetric Conjugate Addition4.2 Asymmetric Allylic Alkylations4.3 Desymmetrization Reactions4.4 Cross-Coupling Reactions4.5 1,2-Additions5 Conclusions

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