Synthesis of pyrrolopyridines (azaindoles)

Ambident heterocyclic reactivity: Alkylation of 2-substituted-4-methylbenzimidazoles

Ambident heterocyclic reactivity: the alkylation of pyrrolopyridines (azaindoles, diazaindenes)

Synthesis of purine-acridine hybrid molecules related to artificial endonucleases

Design, synthesis and characterization of N9/N7-substituted 6-aminopurines as VEGF-R and EGF-R inhibitors.

The N3 : N7 : N9 alkylation patterns for reactions of the lithium, sodium, and potassium salts of adenine with various alkylating agents in dimethyl sulfoxide were determined by 1H n.m.r. spectroscopy. Only for the Li+ salt was any significant effect of ionic association noticed. Of the alkylating agents used, only chloromethyl pivalate gave a concentration dependent alkylation pattern. The latter effect was most pronounced with the heterogeneous alkylation conditions of anhydrous Na2CO3/HCONMe2, adenine, and chloromethyl pivalate; here, increasing concentrations changed the main reaction from N7- to N9-alkylation. Solvent effects on the alkylation patterns were also studied. Within the common dipolar aprotic solvent group, (Me2N)3PO, HCONMe2 and Me2SO, effects were small; in protic solvents, particularly formamide, enhanced N3-alkylation was observed.

M Rasmussen

Papers

Heterocyclic ambident nucleophiles. IV. The alkylation of metal salts of adenine