Premium
Presence of an N ‐6 acetate group shifts the alkylation site of the ambident nucleophile sodium 1‐ N ‐methylisoguanide
Author(s) -
Nachman Ronald J.
Publication year - 1985
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570220403
Subject(s) - chemistry , alkylation , nucleophile , sodium acetate , tautomer , medicinal chemistry , sodium , leaving group , nucleophilic substitution , stereochemistry , organic chemistry , catalysis
Inclusion of an N ‐6 acetate into the ambident nucleophile, sodium 1‐ N ‐methylisoguanide, resulted in a shift in alkylation preference from N ‐9 to N ‐3. The preparation of the N ‐6 acetate of 1‐ N ‐methylisoguanine, 9‐ N ‐acetyl‐1‐ N ‐methylisoguanine (4) , and related acetate analogs are described and evidence presented for their structural determination. Analysis of long range 13 C‐ 1 H coupling data facilitated the structural elucidation of the predominant alkylation products and provided evidence for the unusual N ‐7 hydrogen tautomeric form in one of them, 3‐ N ‐benzyl‐6‐ N ‐acetyl‐1‐ N ‐methylisoguanine (8).