4230-27-7Relevant academic research and scientific papers
Purine N-alkylated derivatives. SRN1 synthesis and functional group transformations
Gharbaoui, Tawfik,Benhida, Rachid,Chastanet, Jacqueline,Lechevallier, Andre,Maillos, Philippe,Beugelmans, Rene
, p. 561 - 574 (2007/10/02)
Purine and its 6-chloro, 6-methoxy, 6-amino and 2-amino-6-chloro derivatives are efficient nucleophiyles in SRN1 reactions with various functionalized gem halo-nitroalkanes as substrates in which good regioselectivity on N9 is observ
Heterocyclic Ambident Nucleophiles. IV* The alkylation of Metal Salts of Adenine
Rasmussen, Malcolm,Hope, Janet M.
, p. 535 - 542 (2007/10/02)
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 heterogenous alkylation conditions of anhydrous Na2CO3/HCONMe2, adenine, and chloromethyl pivalate; here, increasingconcentrations 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.
