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1‐Aminohypoxanthine and analogues
Author(s) -
Scheiner Peter,
Arwin Sara,
Eliacin Manes,
Tu James
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.5570220563
Subject(s) - chemistry , hydrazide , triethyl orthoformate , riboside , hydrolysis , orthoester , carboxylic acid , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , biochemistry
1‐Aminohypoxanthine ( 1a ), a new positional isomer of guanine, has been obtained from 5‐aminoimidazole‐4‐carboxylic acid hydrazide and triethyl orthoformate. Pyrazolo 11 and triazolo 21 analogues of 1 result from similar reactions of the corresponding o ‐aminoazole hydrazides. An indirect synthesis involving excess ortho‐ester and hydrolysis of the resulting intermediate 6 was found most effective for 1 , but 11 may be prepared directly from 3‐aminopyrazole‐4‐carboxylic acid hydazide and orthoesters. Triazoles proved most resistant to fused pyrimidinone formation. The riboside of 1a (1‐aminoinosine) has been synthesized, indicating the versatility of the method.