Premium
Synthesis of 6 H ‐pyrazolo[2,3‐ a ][1,3,5]benzotriazepines
Author(s) -
Peet Norton P.,
Sunder Shyam,
Barbuch Robert J.
Publication year - 1983
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.5570200304
Subject(s) - triethyl orthoformate , chemistry , yield (engineering) , ring (chemistry) , pyrazole , medicinal chemistry , stereochemistry , organic chemistry , materials science , metallurgy , catalysis
Treatment of 5‐amino‐1‐(2‐aminophenyl)‐1 H ‐pyrazole‐4‐carbonitrile ( 15 ) with triethyl orthoformate produces 6 H ‐pyrazolo[2,3‐ a ][1,3,5]benzotriazepine‐3‐carbonitrile ( 16 ). Other members of this novel ring system result from treating 15 with triethyl orthoacetate and triethyl orthopropionate. These latter reactions, which yield homologs 17 and 19 , respectively, of 16 , also produce acyclic Schiff bases. These Schiff bases are useful in determining the position of the triazepine double bond in pyrazolobenzotriazepines 16 , 17 and 19 , using 13 C nmr spectroscopy.