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4,5,8,9‐tetrahydro‐8‐methyl‐9‐oxothieno[3′,2′:5,6]cyclohepta[1,2‐ b ]‐ pyrrole‐7‐acetic acid. A new anti‐inflammatory/analgesic agent
Author(s) -
Goudie A. C.,
Rosenberg H. E.,
Ward R. W.
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.5570200437
Subject(s) - chemistry , pyrrole , morpholine , tricyclic , friedel–crafts reaction , alkylation , acetic acid , ring (chemistry) , medicinal chemistry , organic chemistry , stereochemistry , catalysis
The synthesis of the thienocyclohepta[1, 2‐ b ]pyrrole acid 1 from the morpholide 3 is reported. This novel morpholide was prepared by regiospecific alkylation of the dianion of 4 ‐(1, 3‐dioxobutyl)morpholine with 3‐bromomethylthiophene. Subsequent Knorr pyrrole synthesis led to the morpholide 8b which was converted to the desired tricyclic ring system under Vilsmeier conditions. An alternative route involving Friedel‐Crafts cyclisation was used to prepare the related benzocycloheptapyrrole 2 .