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Alkylation of adenine with t-propargyl chlorides: acetylene/allene ratio and N9/N7 regioselectivity

✍ Scribed by Ramachandra V. Joshi; Jiri Zemlicka

Book ID
104203891
Publisher
Elsevier Science
Year
1993
Tongue
French
Weight
580 KB
Volume
49
Category
Article
ISSN
0040-4020

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✦ Synopsis

Abstmct: Alkylation of aaknine ( 6 ) with dialkylpropargyl chioriaks 3a and 3b gave I@-and fl-acetylenes 7a, 7b and 94.96 accompanied by @-allenes 8a, 8b. Bromoallene 104 gave only 7a and 7b but no allene &a. Reaction of propargyl chloride with 6 led on& to fl-propargyladenine ( 7c ) whereas clJoroallene lob #or&d 7c and allene 8c. The possible reaction

course will be discussed with emphasis on the ir@luenc~ of structure, reagent and solvent on acetylenelallene ratio andi@lfl regioselectivity of alkyhttion. The nonequkalent inethylene groups of 7b and 96 have d8 0.67 and 1.07, respectiveb, appearing as sextets in the IH NMR spectra.

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