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Synthesis of pyrrolo[2,1‐ f ][1,2,4]triazine congeners of nucleic acid purines via the N ‐amination of 2‐substituted pyrroles
Author(s) -
Patil Shirish A.,
Otter Brian A.,
Klein Robert S.
Publication year - 1994
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.5570310415
Subject(s) - chemistry , amidine , hydroxylamine , amination , annulation , triazine , synthon , amide , pyrrole , purine metabolism , hydrazine (antidepressant) , stereochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis , chromatography , enzyme
The synthesis of several new 4‐mono‐ and 2,4‐disubstituted pyrrolo[2,1‐ f ][1,2,4]triazines is described. Key 1‐aminopyrrole‐2‐carbonitrile intermediates 3 and 15 were obtained by N ‐amination of the corresponding pyrrole‐2‐carboxaldehyde followed by CHO → CN conversion with either hydroxylamine‐ O ‐sulfonic acid for 3 or O ‐mesitylenesulfonylhydroxylamine for 15. Cyclization of 3 or 15 with a variety of amidine reagents or, after conversion of 3 to its corresponding amide, base‐catalyzed annulation completed the synthesis of the title products.