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Benzomorphan related compounds. XII 2,5‐Methanothieno[3,2‐ g ]quinolines as rigid bridged thienomorphans
Author(s) -
Bosch J.,
Alvarez M.,
Granados R.
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.5570170423
Subject(s) - chemistry , quinoline , acrylate , dihydropyridine , ethyl acrylate , stereochemistry , medicinal chemistry , organic chemistry , calcium , monomer , polymer
The preparation of a 1,2,3,4,4a,5,9,9a‐octahydro‐2,5‐methanothieno[3,2‐ g ]quinoline, which can be considered as a rigid thieno[3,2‐ f ]morphan system due to an additional two‐atoms bridge between the 3 and 9 positions of the morphan nucleus, is described. The synthetic route involved the acidic cyclization of a 3‐(2‐thenyl)‐2‐azabicyclo[2.2.2]oct‐7‐ene, obtained by the Diels‐Alder reaction between 1,3,4‐trimethyl‐2‐(2‐thenyl)‐1,2‐dihydropyridine and ethyl acrylate.