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Synthesis of novel 1,3‐oxazino[6,5‐ b ]indole‐2,4‐(3 H ,9 H )‐dione and 2 H ‐1,3,5‐oxadiazino[3,2‐ a ]indole‐2,4‐(3 H )‐dione from oxindoles
Author(s) -
Gallaschun Randall J.,
Schnur Rodney C.
Publication year - 1992
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.5570290214
Subject(s) - chemistry , indole test , phosgene , triethylamine , ring (chemistry) , stereochemistry , tetrahydrofuran , tricyclic , serine protease , organic chemistry , protease , solvent , enzyme
Two novel tricyclic ring systems were designed as serine protease inhibitors and synthesized from oxindoles; the first series, 1,3‐oxazino[6,5‐ b ]indole‐2,4‐(3 H ,9 H )‐diones, were prepared from 2,3‐dihydro‐2‐oxo‐(1 H )‐indole‐3‐carboxamides and phosgene in tetrahydrofuran with triethylamine. The second, a 2 H ‐1,3,5‐oxadiazino[3,2‐ a ]indole‐2,4‐(3 H )‐dione was made using a similar cyclization on 2,3‐dihydro‐2‐oxo‐ N ‐phenyl‐(1 H )‐indole‐1‐carboxamide.