Premium
The synthesis of 11 H ‐1,2,4‐triazolo[4,3‐ b ]pyridazino[4,5‐ b ]indoles,11 H ‐tetrazolo[4,5‐ b ]pyridazino[4,5‐ b ]indoles and 1,2,4‐triazolo[3,4‐ f ]‐1,2,4‐triazino[4,5‐ a ]indoles
Author(s) -
Monge Vega A.,
Aldana I.,
Rabbani M. M.,
FernandezAlvarez E.
Publication year - 1980
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.5570170116
Subject(s) - chemistry , hydrazine (antidepressant) , acylation , formic acid , medicinal chemistry , indole test , stereochemistry , organic chemistry , catalysis , chromatography
This paper describes the synthesis of the previously unknown 11 H ‐1,2,4‐triazolo[4,3‐ b ]pyridazino[4,5‐ b ]indoles (2) and 11 H ‐tetrazolo[4,5‐ b ]pyridazino[4,5‐ b ]indoles (3) from 4‐hydrazino‐5 H ‐pyridazino[4,5‐ b ]indoles (1) , as well as the synthesis of 1,2,4‐triazolo[3,4‐ f ]‐1,2,4‐triazino‐[4,5‐ a ]indoles (10) from 2‐indolecarbohydrazide (4) . Compounds 2 were obtained by acylation of compounds 1 , followed of thermal cyclization and compounds 3 by treating compounds 1 with nitrous acid. The reactions of compound 4 with formic acid or ethyl orthoformiate gave 1,2‐dihydro‐1‐oxo‐1,2,4‐triazino[4,5‐ a ]indole (6) . Treating this last compound with phosphorus oxychloride or phosphorus pentasulfide, followed by hydrazine, gave 1‐hydrazino‐1,2,4‐triazino‐[4,5‐ a ]indole (9) . Acylation of this last compound, followed of cyclization gave compounds 10 . All the compounds were characterized by elemental analysis and ir and 1 H‐nmr spectra.