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Synthesis of 3‐amino‐5 H ‐1,2,3‐triazino[5,4‐ b ]indol‐4‐one. New compounds with blood platelet antiaggregation activity
Author(s) -
Monge A.,
Aldana I.,
Arrarás J. A.,
FernándezAlvarez E.
Publication year - 1991
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.5570280304
Subject(s) - chemistry , hydrazine (antidepressant) , hydrate , azine , boiling , dimethylformamide , ethanol , medicinal chemistry , derivative (finance) , organic chemistry , nuclear chemistry , chromatography , solvent , financial economics , economics
Starting with 3‐aminoindole‐2‐carbohydrazide 1 a series of arylidene hydrazones 2 was obtained with good yields (79–85%). Upon treating 2 with nitrous acid a series of 3‐arylidineamino‐5 H ‐1,2,3‐triazino[5,4‐ b ]indol‐4‐ones 3 was obtained (80–86%). The reaction of 4‐methoxybenzylidene derivative 3e with hydrazine hydrate, in ethanol, gave 3‐amino‐5 H ‐1,2,3‐triazino[5,4‐ b ]indol‐4‐one 4 (64%). However, by treating 3e in boiling hydrate, 3‐aminoindole‐2‐carbaldehyde azine 5 was obtained (44%). By boiling 1 in N,N ‐dimethylformamide, 3‐amino‐5 H ‐pyrimido[5,4‐ b ]indol‐4‐one, 6 was obtained (52%).