Synthesis of 6 H ‐pyrazolo[2,3‐ a ][1,3,5]benzotriazepines | Zendy

Peet Norton P. | Zendy; Sunder Shyam | Zendy; Barbuch Robert J. | Zendy

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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.

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