Synthesis of pyrrolo[2,1‐ f ][1,2,4]triazine congeners of nucleic acid purines  via  the  N ‐amination of 2‐substituted pyrroles | Zendy

Patil Shirish A. | Zendy; Otter Brian A. | Zendy; Klein Robert S. | Zendy

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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.

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