Presence of an  N ‐6 acetate group shifts the alkylation site of the ambident nucleophile sodium 1‐ N ‐methylisoguanide | Zendy

Nachman Ronald J. | Zendy

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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).

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