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Benzomorphan related compounds. V . Synthesis of thienomorphans
Author(s) -
Alvarez M.,
Bosch J.,
Cranados R.,
López F.
Publication year - 1978
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.5570150204
Subject(s) - chemistry , stereochemistry , series (stratigraphy) , combinatorial chemistry , paleontology , biology
Abstract A series of thieno [2,3‐ƒ]‐, [3,2‐ƒ]‐ and [3,4‐ƒ]morphans prepared both by the Grewe synthesis and by the reaction of 2‐cyanopyridines with 3‐thienyllithium is described. Furthermore, a new synthetic route to thieno [2,3‐ƒ] morphans from 3‐ketotetrahydrolhiophene is reported. Separation and assignment of the α‐ and β‐diastereomerie structures by means of nmr data is reported. Some side products were isolated and their structures were confirmed on the basis of their spectral data. Mechanisms for their formation are proposed.