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Synthesis and Reactions of Pyridinethiones
Author(s) -
Köditz Jens,
Rudorf WolfDieter,
Hartung Helmut,
Heinemann Frank
Publication year - 1993
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1993199301159
Subject(s) - chemistry , combinatorial chemistry
The push‐pull systems 1 and 7 undergo regioselective cyclization with cyanothioacetamide 2 leading to pyridinethiones 3 and 8 . Subsequent S ‐alkylation affords the alkylthio derivatives 5 and 10 . Thieno[2,3‐ b ]pyridines 6 and 11 are formed by using an α‐CH‐acidic halogen compound as alkylating agent, followed by Thorpe‐Ziegler reaction. The cyano group in 6d and 11d can be converted into an imidazoline ring by treatment with 1,2‐diaminoethane hydrate and carbon disulfide. Structures are supported by spectral data as well as by X‐ray analysis of 5d .