Benzomorphan related compounds. XII   2,5‐Methanothieno[3,2‐ g ]quinolines as rigid bridged thienomorphans | Zendy

Bosch J. | Zendy; Alvarez M. | Zendy; Granados R. | Zendy

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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.

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